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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (113)transporters (1) Show 114 proteins XML

enzymes (113)transporters (1) Show 114 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2022-03-07 02:49:12 UTC

HMDB ID

HMDB0002009

Secondary Accession Numbers

HMDB0059627
HMDB02009
HMDB59627

Metabolite Identification

Common Name

Crotonoyl-CoA

Description

Crotonoyl-CoA (CAS: 992-67-6) is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of acyl-coenzyme A oxidases 1, 2, and 3 (EC 1.3.3.6) corresponding to palmitoyl, branched-chain, and pristanoyl, respectively. In peroxisomal fatty acid beta-oxidation, these enzymes produce hydrogen peroxide. Abnormalities in this group of enzymes are linked to coma, dehydration, diabetes, fatty liver, hyperinsulinemia, hyperlipidemia, and leukodystrophy. Crotonoyl-CoA is also a substrate of a group of enzymes called acyl-coenzyme A dehydrogenases (EC 1.3.99-, 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids or branched-chain amino acids in the mitochondria (PMID: 7698750 ). Acyl-coenzyme A dehydrogenase has been shown to contribute to kidney-associated diseases, such as adrenogential syndrome, kidney failure, kidney tubular necrosis, homocystinuria, as well as other diseases including cretinism, encephalopathy, hypoglycemia, and medium-chain acyl-CoA dehydrogenase deficiency. The gene (ACADS) also plays a role in theta oscillation during sleep. In addition, crotonoyl-CoA is the substrate of enoyl-coenzyme A hydratase (EC 4.2.1.17) in the mitochondria during lysine degradation and tryptophan metabolism as well as benzoate degradation via CoA ligation. Crotonoyl-CoA is the product of this enzyme in butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-hydroxybutyryl-CoA dehydratase (EC 4.2.1.55), glutaconyl-CoA decarboxylase (EC 4.1.1.70), vinylacetyl-CoA delta-isomerase (EC 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (EC 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl-CoA is produced by glutaryl-coenzyme A dehydrogenase (EC 1.3.99.7). This enzyme is linked to glutaric aciduria type I, metabolic diseases, movement disorders, myelinopathy, and nervous system diseases.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222023462D          

 60 62  0  0  1  0            999 V2000
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14 10  1  1  0  0  0
 15  6  1  0  0  0  0
 16  5  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25 11  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  8  1  4  0  0  0
 27 15  2  0  0  0  0
 28  7  1  4  0  0  0
 28 23  2  0  0  0  0
 29 12  2  0  0  0  0
 29 21  1  0  0  0  0
 30 12  1  0  0  0  0
 30 22  2  0  0  0  0
 31 13  2  0  0  0  0
 31 17  1  0  0  0  0
 32 13  1  0  0  0  0
 32 22  1  0  0  0  0
 24 32  1  1  0  0  0
 33 15  1  0  0  0  0
 34 16  2  0  0  0  0
 18 35  1  6  0  0  0
 20 36  1  6  0  0  0
 37 23  1  0  0  0  0
 45 10  1  0  0  0  0
 46 11  1  0  0  0  0
 47 14  1  0  0  0  0
 47 24  1  0  0  0  0
 19 48  1  1  0  0  0
 50 38  1  0  0  0  0
 50 39  1  0  0  0  0
 50 40  2  0  0  0  0
 50 48  1  0  0  0  0
 51 41  1  0  0  0  0
 51 42  2  0  0  0  0
 51 45  1  0  0  0  0
 51 49  1  0  0  0  0
 52 43  1  0  0  0  0
 52 44  2  0  0  0  0
 52 46  1  0  0  0  0
 52 49  1  0  0  0  0
 53  9  1  0  0  0  0
 53 16  1  0  0  0  0
 54  4  1  0  0  0  0
 55  5  1  0  0  0  0
 14 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 20 59  1  6  0  0  0
 24 60  1  6  0  0  0
M  END

HMDB0002009
     RDKit          3D
Crotonoyl-CoA
 93 95  0  0  0  0  0  0  0  0999 V2000
   12.6678    3.1619    3.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4797    2.6195    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350    2.8417    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    2.3053    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3488    1.6586    1.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9548    2.5854   -1.1261 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6152    1.7853   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7707    0.3064   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -0.3484   -0.7314 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -0.3382   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734    0.2307   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053   -1.0107    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -1.1435    1.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -1.9284    0.7404 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.2629    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -1.8639    1.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -3.0786   -0.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7291   -3.1464   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -2.9511   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738   -3.3563    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -4.0757   -1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -1.7050   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -0.5338   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7808   -0.9255 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4970    1.5272   -1.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8797    0.2319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7849    0.3262   -1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -0.1814   -1.2601 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6001   -1.5001   -1.9523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -0.4597    0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222    0.8587   -1.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    1.0749   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768    1.9791   -0.7406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3043    1.3686   -1.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5385    1.1833   -1.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2389    0.0305   -1.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8685   -0.8814   -2.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8771   -1.7827   -2.7029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9021   -1.4352   -1.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1429   -1.9837   -1.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6046   -3.1468   -2.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9418   -1.3785   -0.7689 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5461   -0.2551   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3360    0.2453   -0.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4749   -0.3089   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260    0.9984    0.3653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2721    0.9618    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636    2.1624    0.5307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8215    3.3452    0.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5988    4.0896    2.2166 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1280    4.0109    2.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4169    3.3186    3.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0308    5.6997    2.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8590    2.5214    4.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5929    3.1209    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4716    4.1996    3.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690    2.0471    3.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0790    3.4268    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6409    2.0065   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5529    2.1913   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852   -0.1236   -2.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7739    0.0385   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4278   -0.8306   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6849   -2.0126    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111   -0.4459    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -0.0982    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7599   -1.5229    2.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -2.2549   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264   -4.1632    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515   -2.2368   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -2.5286    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -4.2266    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319   -3.7555    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -4.9963   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013   -3.8464   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -4.0804   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313   -1.8843   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -1.5806   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219    2.0405    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -1.3993    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078    0.1359   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    1.4772    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764    2.8834   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1171    2.1368   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9082   -0.8708   -3.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8954   -3.7515   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5980   -3.4437   -2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1894    0.2216    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.0151    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9591    0.8667    2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6145    1.8694    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3987    3.2893    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8189    5.9086    2.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 35 46  1  0
 46 47  1  0
 46 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  2  0
 50 52  1  0
 50 53  1  0
 48 33  1  0
 45 36  1  0
 45 39  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  0
  3 58  1  0
  7 59  1  0
  7 60  1  0
  8 61  1  0
  8 62  1  0
  9 63  1  0
 12 64  1  0
 12 65  1  0
 13 66  1  0
 13 67  1  0
 14 68  1  0
 17 69  1  1
 18 70  1  0
 20 71  1  0
 20 72  1  0
 20 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 26 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  6
 35 84  1  1
 37 85  1  0
 41 86  1  0
 41 87  1  0
 43 88  1  0
 46 89  1  6
 47 90  1  0
 48 91  1  1
 52 92  1  0
 53 93  1  0
M  END


  Mrv1652306222023462D          

 60 62  0  0  1  0            999 V2000
    1.5749   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5383   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8883   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8554   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5698   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7120   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9975   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    8.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7133   12.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0280    6.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3874    5.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5711    8.2834    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1409   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   14.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6931    5.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8768    8.0058    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  -11.3248    8.6189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   14.0584    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  -13.4468    5.2101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6069    6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   14.4709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4643    7.2914    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7133   13.2334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5330    4.3896    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4264   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2843   14.0584    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1142    5.6950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.2743    6.8511    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9394    5.2101    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7999    6.5377    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1409   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5685   13.2334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6973    8.0921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   14.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   15.2959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3312    9.3648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4353   10.5910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2701   10.5300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5547   10.6478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7297    9.2189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2527   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6027   11.1709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8567    9.5209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.9959    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6574    7.4629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4963    9.4259    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   10.3459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8832    9.9779    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1422    9.9334    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4277   11.1709    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2830   14.4709    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8604   13.2334    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1459   15.2959    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6143    9.1072    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1725    8.7760    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1533    7.8119    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9988   13.6459    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.2882    7.2482    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 14 10  1  1  0  0  0
 15  6  1  0  0  0  0
 16  5  1  0  0  0  0
 19 14  1  0  0  0  0
 19 18  1  0  0  0  0
 21 17  2  0  0  0  0
 22 17  1  0  0  0  0
 23 20  1  0  0  0  0
 24 18  1  0  0  0  0
 25  2  1  0  0  0  0
 25  3  1  0  0  0  0
 25 11  1  0  0  0  0
 25 20  1  0  0  0  0
 26 21  1  0  0  0  0
 27  8  1  4  0  0  0
 27 15  2  0  0  0  0
 28  7  1  4  0  0  0
 28 23  2  0  0  0  0
 29 12  2  0  0  0  0
 29 21  1  0  0  0  0
 30 12  1  0  0  0  0
 30 22  2  0  0  0  0
 31 13  2  0  0  0  0
 31 17  1  0  0  0  0
 32 13  1  0  0  0  0
 32 22  1  0  0  0  0
 24 32  1  1  0  0  0
 33 15  1  0  0  0  0
 34 16  2  0  0  0  0
 18 35  1  6  0  0  0
 20 36  1  6  0  0  0
 37 23  1  0  0  0  0
 45 10  1  0  0  0  0
 46 11  1  0  0  0  0
 47 14  1  0  0  0  0
 47 24  1  0  0  0  0
 19 48  1  1  0  0  0
 50 38  1  0  0  0  0
 50 39  1  0  0  0  0
 50 40  2  0  0  0  0
 50 48  1  0  0  0  0
 51 41  1  0  0  0  0
 51 42  2  0  0  0  0
 51 45  1  0  0  0  0
 51 49  1  0  0  0  0
 52 43  1  0  0  0  0
 52 44  2  0  0  0  0
 52 46  1  0  0  0  0
 52 49  1  0  0  0  0
 53  9  1  0  0  0  0
 53 16  1  0  0  0  0
 54  4  1  0  0  0  0
 55  5  1  0  0  0  0
 14 56  1  6  0  0  0
 18 57  1  1  0  0  0
 19 58  1  1  0  0  0
 20 59  1  6  0  0  0
 24 60  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0002009

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(C)=C(\[H])C(=O)SCCN=C(O)CCN=C(O)[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/b5-4+/t14-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
KFWWCMJSYSSPSK-PAXLJYGASA-N

> <FORMULA>
C25H40N7O17P3S

> <MOLECULAR_WEIGHT>
835.608

> <EXACT_MASS>
835.141423115

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
93

> <JCHEM_AVERAGE_POLARIZABILITY>
75.88685494575334

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

> <ALOGPS_LOGP>
0.03

> <JCHEM_LOGP>
-4.24267576937707

> <ALOGPS_LOGS>
-2.17

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8865544644008798

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8191671959681748

> <JCHEM_PKA_STRONGEST_BASIC>
6.43491190778609

> <JCHEM_POLAR_SURFACE_AREA>
370.61000000000007

> <JCHEM_REFRACTIVITY>
183.57260000000008

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002009
     RDKit          3D
Crotonoyl-CoA
 93 95  0  0  0  0  0  0  0  0999 V2000
   12.6678    3.1619    3.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4797    2.6195    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350    2.8417    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    2.3053    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3488    1.6586    1.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9548    2.5854   -1.1261 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6152    1.7853   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7707    0.3064   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -0.3484   -0.7314 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -0.3382   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734    0.2307   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053   -1.0107    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -1.1435    1.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -1.9284    0.7404 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.2629    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -1.8639    1.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -3.0786   -0.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7291   -3.1464   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -2.9511   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738   -3.3563    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -4.0757   -1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -1.7050   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -0.5338   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7808   -0.9255 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4970    1.5272   -1.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8797    0.2319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7849    0.3262   -1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -0.1814   -1.2601 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6001   -1.5001   -1.9523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -0.4597    0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222    0.8587   -1.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    1.0749   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768    1.9791   -0.7406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3043    1.3686   -1.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5385    1.1833   -1.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2389    0.0305   -1.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8685   -0.8814   -2.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8771   -1.7827   -2.7029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9021   -1.4352   -1.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1429   -1.9837   -1.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6046   -3.1468   -2.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9418   -1.3785   -0.7689 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5461   -0.2551   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3360    0.2453   -0.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4749   -0.3089   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260    0.9984    0.3653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2721    0.9618    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636    2.1624    0.5307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8215    3.3452    0.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5988    4.0896    2.2166 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1280    4.0109    2.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4169    3.3186    3.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0308    5.6997    2.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8590    2.5214    4.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5929    3.1209    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4716    4.1996    3.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690    2.0471    3.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0790    3.4268    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6409    2.0065   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5529    2.1913   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852   -0.1236   -2.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7739    0.0385   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4278   -0.8306   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6849   -2.0126    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111   -0.4459    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -0.0982    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7599   -1.5229    2.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -2.2549   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264   -4.1632    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515   -2.2368   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -2.5286    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -4.2266    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319   -3.7555    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -4.9963   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013   -3.8464   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -4.0804   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313   -1.8843   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -1.5806   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219    2.0405    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -1.3993    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078    0.1359   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    1.4772    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764    2.8834   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1171    2.1368   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9082   -0.8708   -3.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8954   -3.7515   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5980   -3.4437   -2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1894    0.2216    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.0151    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9591    0.8667    2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6145    1.8694    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3987    3.2893    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8189    5.9086    2.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 35 46  1  0
 46 47  1  0
 46 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  2  0
 50 52  1  0
 50 53  1  0
 48 33  1  0
 45 36  1  0
 45 39  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  0
  3 58  1  0
  7 59  1  0
  7 60  1  0
  8 61  1  0
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 12 64  1  0
 12 65  1  0
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 17 69  1  1
 18 70  1  0
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 32 81  1  0
 32 82  1  0
 33 83  1  6
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 37 85  1  0
 41 86  1  0
 41 87  1  0
 43 88  1  0
 46 89  1  6
 47 90  1  0
 48 91  1  1
 52 92  1  0
 53 93  1  0
M  END

HEADER    PROTEIN                                 22-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-20         0                                  
HETATM    1  C   UNK     0       2.940  27.012   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -15.938  24.702   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -12.858  24.702   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.606  26.242   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.272  27.012   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -9.063  26.242   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -10.397  27.012   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.062  27.012   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.729  26.242   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -18.399  16.232   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.398  23.162   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -26.186  12.162   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -21.256  10.870   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -19.733  15.462   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.730  27.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.061  26.242   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -23.694  10.352   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -22.170  14.944   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -21.140  16.089   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -14.398  26.242   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -25.101   9.726   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -23.533  11.884   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -13.064  27.012   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -21.400  13.611   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -14.398  24.702   0.000  0.00  0.00           C+0
HETATM   26  N   UNK     0     -25.262   8.194   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      -6.396  26.242   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0     -11.731  26.242   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0     -26.347  10.631   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0     -24.779  12.789   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -22.287   9.726   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -22.026  12.204   0.000  0.00  0.00           N+0
HETATM   33  O   UNK     0      -7.730  28.552   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.061  24.702   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0     -23.702  15.105   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -15.732  27.012   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0     -13.064  28.552   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0     -19.285  17.481   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -21.346  19.770   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0     -19.171  19.656   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0     -17.835  19.876   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0     -16.295  17.209   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0     -17.272  20.852   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -14.192  20.852   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0     -18.399  17.772   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0     -15.732  22.392   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0     -19.894  13.931   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0     -21.460  17.595   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -15.732  19.312   0.000  0.00  0.00           O+0
HETATM   50  P   UNK     0     -20.315  18.625   0.000  0.00  0.00           P+0
HETATM   51  P   UNK     0     -17.065  18.542   0.000  0.00  0.00           P+0
HETATM   52  P   UNK     0     -15.732  20.852   0.000  0.00  0.00           P+0
HETATM   53  S   UNK     0      -2.395  27.012   0.000  0.00  0.00           S+0
HETATM   54  H   UNK     0       1.606  24.702   0.000  0.00  0.00           H+0
HETATM   55  H   UNK     0       0.272  28.552   0.000  0.00  0.00           H+0
HETATM   56  H   UNK     0     -19.813  17.000   0.000  0.00  0.00           H+0
HETATM   57  H   UNK     0     -22.722  16.382   0.000  0.00  0.00           H+0
HETATM   58  H   UNK     0     -20.819  14.582   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0     -13.064  25.472   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0     -22.938  13.530   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   25                                                            
CONECT    3   25                                                            
CONECT    4    1    5   54                                                  
CONECT    5    4   16   55                                                  
CONECT    6    7   15                                                       
CONECT    7    6   28                                                       
CONECT    8    9   27                                                       
CONECT    9    8   53                                                       
CONECT   10   14   45                                                       
CONECT   11   25   46                                                       
CONECT   12   29   30                                                       
CONECT   13   31   32                                                       
CONECT   14   10   19   47   56                                             
CONECT   15    6   27   33                                                  
CONECT   16    5   34   53                                                  
CONECT   17   21   22   31                                                  
CONECT   18   19   24   35   57                                             
CONECT   19   14   18   48   58                                             
CONECT   20   23   25   36   59                                             
CONECT   21   17   26   29                                                  
CONECT   22   17   30   32                                                  
CONECT   23   20   28   37                                                  
CONECT   24   18   32   47   60                                             
CONECT   25    2    3   11   20                                             
CONECT   26   21                                                            
CONECT   27    8   15                                                       
CONECT   28    7   23                                                       
CONECT   29   12   21                                                       
CONECT   30   12   22                                                       
CONECT   31   13   17                                                       
CONECT   32   13   22   24                                                  
CONECT   33   15                                                            
CONECT   34   16                                                            
CONECT   35   18                                                            
CONECT   36   20                                                            
CONECT   37   23                                                            
CONECT   38   50                                                            
CONECT   39   50                                                            
CONECT   40   50                                                            
CONECT   41   51                                                            
CONECT   42   51                                                            
CONECT   43   52                                                            
CONECT   44   52                                                            
CONECT   45   10   51                                                       
CONECT   46   11   52                                                       
CONECT   47   14   24                                                       
CONECT   48   19   50                                                       
CONECT   49   51   52                                                       
CONECT   50   38   39   40   48                                             
CONECT   51   41   42   45   49                                             
CONECT   52   43   44   46   49                                             
CONECT   53    9   16                                                       
CONECT   54    4                                                            
CONECT   55    5                                                            
CONECT   56   14                                                            
CONECT   57   18                                                            
CONECT   58   19                                                            
CONECT   59   20                                                            
CONECT   60   24                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  124    0
END

COMPND    HMDB0002009
HETATM    1  C1  UNL     1      12.668   3.162   3.312  1.00  0.00           C  
HETATM    2  C2  UNL     1      11.480   2.620   2.587  1.00  0.00           C  
HETATM    3  C3  UNL     1      11.335   2.842   1.316  1.00  0.00           C  
HETATM    4  C4  UNL     1      10.160   2.305   0.595  1.00  0.00           C  
HETATM    5  O1  UNL     1       9.349   1.659   1.275  1.00  0.00           O  
HETATM    6  S1  UNL     1       9.955   2.585  -1.126  1.00  0.00           S  
HETATM    7  C5  UNL     1       8.615   1.785  -1.958  1.00  0.00           C  
HETATM    8  C6  UNL     1       8.771   0.306  -1.999  1.00  0.00           C  
HETATM    9  N1  UNL     1       8.636  -0.348  -0.731  1.00  0.00           N  
HETATM   10  C7  UNL     1       7.355  -0.338  -0.069  1.00  0.00           C  
HETATM   11  O2  UNL     1       6.373   0.231  -0.590  1.00  0.00           O  
HETATM   12  C8  UNL     1       7.205  -1.011   1.234  1.00  0.00           C  
HETATM   13  C9  UNL     1       5.770  -1.144   1.686  1.00  0.00           C  
HETATM   14  N2  UNL     1       5.008  -1.928   0.740  1.00  0.00           N  
HETATM   15  C10 UNL     1       3.631  -2.263   0.920  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.042  -1.864   1.940  1.00  0.00           O  
HETATM   17  C11 UNL     1       2.988  -3.079  -0.130  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.729  -3.146  -1.312  1.00  0.00           O  
HETATM   19  C12 UNL     1       1.530  -2.951  -0.282  1.00  0.00           C  
HETATM   20  C13 UNL     1       0.874  -3.356   1.036  1.00  0.00           C  
HETATM   21  C14 UNL     1       1.104  -4.076  -1.265  1.00  0.00           C  
HETATM   22  C15 UNL     1       0.965  -1.705  -0.835  1.00  0.00           C  
HETATM   23  O5  UNL     1       1.200  -0.534  -0.170  1.00  0.00           O  
HETATM   24  P1  UNL     1       0.430   0.781  -0.926  1.00  0.00           P  
HETATM   25  O6  UNL     1       1.497   1.527  -1.711  1.00  0.00           O  
HETATM   26  O7  UNL     1      -0.148   1.880   0.232  1.00  0.00           O  
HETATM   27  O8  UNL     1      -0.785   0.326  -1.969  1.00  0.00           O  
HETATM   28  P2  UNL     1      -2.201  -0.181  -1.260  1.00  0.00           P  
HETATM   29  O9  UNL     1      -2.600  -1.500  -1.952  1.00  0.00           O  
HETATM   30  O10 UNL     1      -2.080  -0.460   0.379  1.00  0.00           O  
HETATM   31  O11 UNL     1      -3.522   0.859  -1.576  1.00  0.00           O  
HETATM   32  C16 UNL     1      -4.268   1.075  -0.446  1.00  0.00           C  
HETATM   33  C17 UNL     1      -5.477   1.979  -0.741  1.00  0.00           C  
HETATM   34  O12 UNL     1      -6.304   1.369  -1.673  1.00  0.00           O  
HETATM   35  C18 UNL     1      -7.539   1.183  -1.101  1.00  0.00           C  
HETATM   36  N3  UNL     1      -8.239   0.030  -1.636  1.00  0.00           N  
HETATM   37  C19 UNL     1      -7.869  -0.881  -2.539  1.00  0.00           C  
HETATM   38  N4  UNL     1      -8.877  -1.783  -2.703  1.00  0.00           N  
HETATM   39  C20 UNL     1      -9.902  -1.435  -1.891  1.00  0.00           C  
HETATM   40  C21 UNL     1     -11.143  -1.984  -1.659  1.00  0.00           C  
HETATM   41  N5  UNL     1     -11.605  -3.147  -2.314  1.00  0.00           N  
HETATM   42  N6  UNL     1     -11.942  -1.379  -0.769  1.00  0.00           N  
HETATM   43  C22 UNL     1     -11.546  -0.255  -0.109  1.00  0.00           C  
HETATM   44  N7  UNL     1     -10.336   0.245  -0.360  1.00  0.00           N  
HETATM   45  C23 UNL     1      -9.475  -0.309  -1.244  1.00  0.00           C  
HETATM   46  C24 UNL     1      -7.226   0.998   0.365  1.00  0.00           C  
HETATM   47  O13 UNL     1      -8.272   0.962   1.214  1.00  0.00           O  
HETATM   48  C25 UNL     1      -6.264   2.162   0.531  1.00  0.00           C  
HETATM   49  O14 UNL     1      -6.821   3.345   0.769  1.00  0.00           O  
HETATM   50  P3  UNL     1      -6.599   4.090   2.217  1.00  0.00           P  
HETATM   51  O15 UNL     1      -5.128   4.011   2.572  1.00  0.00           O  
HETATM   52  O16 UNL     1      -7.417   3.319   3.503  1.00  0.00           O  
HETATM   53  O17 UNL     1      -7.031   5.700   2.273  1.00  0.00           O  
HETATM   54  H1  UNL     1      12.859   2.521   4.210  1.00  0.00           H  
HETATM   55  H2  UNL     1      13.593   3.121   2.669  1.00  0.00           H  
HETATM   56  H3  UNL     1      12.472   4.200   3.566  1.00  0.00           H  
HETATM   57  H4  UNL     1      10.769   2.047   3.154  1.00  0.00           H  
HETATM   58  H5  UNL     1      12.079   3.427   0.785  1.00  0.00           H  
HETATM   59  H6  UNL     1       7.641   2.007  -1.434  1.00  0.00           H  
HETATM   60  H7  UNL     1       8.553   2.191  -3.016  1.00  0.00           H  
HETATM   61  H8  UNL     1       7.985  -0.124  -2.665  1.00  0.00           H  
HETATM   62  H9  UNL     1       9.774   0.039  -2.440  1.00  0.00           H  
HETATM   63  H10 UNL     1       9.428  -0.831  -0.266  1.00  0.00           H  
HETATM   64  H11 UNL     1       7.685  -2.013   1.167  1.00  0.00           H  
HETATM   65  H12 UNL     1       7.811  -0.446   1.982  1.00  0.00           H  
HETATM   66  H13 UNL     1       5.345  -0.098   1.680  1.00  0.00           H  
HETATM   67  H14 UNL     1       5.760  -1.523   2.715  1.00  0.00           H  
HETATM   68  H15 UNL     1       5.528  -2.255  -0.115  1.00  0.00           H  
HETATM   69  H16 UNL     1       3.126  -4.163   0.286  1.00  0.00           H  
HETATM   70  H17 UNL     1       3.951  -2.237  -1.673  1.00  0.00           H  
HETATM   71  H18 UNL     1       0.805  -2.529   1.743  1.00  0.00           H  
HETATM   72  H19 UNL     1       1.454  -4.227   1.430  1.00  0.00           H  
HETATM   73  H20 UNL     1      -0.132  -3.755   0.770  1.00  0.00           H  
HETATM   74  H21 UNL     1       1.532  -4.996  -0.854  1.00  0.00           H  
HETATM   75  H22 UNL     1       1.601  -3.846  -2.228  1.00  0.00           H  
HETATM   76  H23 UNL     1       0.001  -4.080  -1.393  1.00  0.00           H  
HETATM   77  H24 UNL     1      -0.131  -1.884  -0.994  1.00  0.00           H  
HETATM   78  H25 UNL     1       1.371  -1.581  -1.886  1.00  0.00           H  
HETATM   79  H26 UNL     1      -1.122   2.041   0.129  1.00  0.00           H  
HETATM   80  H27 UNL     1      -2.202  -1.399   0.626  1.00  0.00           H  
HETATM   81  H28 UNL     1      -4.708   0.136  -0.011  1.00  0.00           H  
HETATM   82  H29 UNL     1      -3.634   1.477   0.362  1.00  0.00           H  
HETATM   83  H30 UNL     1      -5.076   2.883  -1.178  1.00  0.00           H  
HETATM   84  H31 UNL     1      -8.117   2.137  -1.272  1.00  0.00           H  
HETATM   85  H32 UNL     1      -6.908  -0.871  -3.040  1.00  0.00           H  
HETATM   86  H33 UNL     1     -10.895  -3.751  -2.795  1.00  0.00           H  
HETATM   87  H34 UNL     1     -12.598  -3.444  -2.348  1.00  0.00           H  
HETATM   88  H35 UNL     1     -12.189   0.222   0.597  1.00  0.00           H  
HETATM   89  H36 UNL     1      -6.673   0.015   0.425  1.00  0.00           H  
HETATM   90  H37 UNL     1      -7.959   0.867   2.130  1.00  0.00           H  
HETATM   91  H38 UNL     1      -5.614   1.869   1.374  1.00  0.00           H  
HETATM   92  H39 UNL     1      -8.399   3.289   3.320  1.00  0.00           H  
HETATM   93  H40 UNL     1      -7.819   5.909   2.840  1.00  0.00           H  
CONECT    1    2   54   55   56
CONECT    2    3    3   57
CONECT    3    4   58
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   59   60
CONECT    8    9   61   62
CONECT    9   10   63
CONECT   10   11   11   12
CONECT   12   13   64   65
CONECT   13   14   66   67
CONECT   14   15   68
CONECT   15   16   16   17
CONECT   17   18   19   69
CONECT   18   70
CONECT   19   20   21   22
CONECT   20   71   72   73
CONECT   21   74   75   76
CONECT   22   23   77   78
CONECT   23   24
CONECT   24   25   25   26   27
CONECT   26   79
CONECT   27   28
CONECT   28   29   29   30   31
CONECT   30   80
CONECT   31   32
CONECT   32   33   81   82
CONECT   33   34   48   83
CONECT   34   35
CONECT   35   36   46   84
CONECT   36   37   45
CONECT   37   38   38   85
CONECT   38   39
CONECT   39   40   40   45
CONECT   40   41   42
CONECT   41   86   87
CONECT   42   43   43
CONECT   43   44   88
CONECT   44   45   45
CONECT   46   47   48   89
CONECT   47   90
CONECT   48   49   91
CONECT   49   50
CONECT   50   51   51   52   53
CONECT   52   92
CONECT   53   93
END

HMDB0002009
     RDKit          3D
Crotonoyl-CoA
 93 95  0  0  0  0  0  0  0  0999 V2000
   12.6678    3.1619    3.3116 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4797    2.6195    2.5865 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3350    2.8417    1.3163 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1596    2.3053    0.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3488    1.6586    1.2752 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9548    2.5854   -1.1261 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.6152    1.7853   -1.9579 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7707    0.3064   -1.9991 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6355   -0.3484   -0.7314 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547   -0.3382   -0.0687 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3734    0.2307   -0.5896 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2053   -1.0107    1.2345 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7705   -1.1435    1.6858 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0080   -1.9284    0.7404 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312   -2.2629    0.9197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0423   -1.8639    1.9395 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -3.0786   -0.1300 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7291   -3.1464   -1.3123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5298   -2.9511   -0.2818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8738   -3.3563    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1036   -4.0757   -1.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9654   -1.7050   -0.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2005   -0.5338   -0.1698 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4295    0.7808   -0.9255 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.4970    1.5272   -1.7107 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482    1.8797    0.2319 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7849    0.3262   -1.9693 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2014   -0.1814   -1.2601 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.6001   -1.5001   -1.9523 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0797   -0.4597    0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5222    0.8587   -1.5762 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    1.0749   -0.4462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4768    1.9791   -0.7406 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3043    1.3686   -1.6728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5385    1.1833   -1.1010 C   0  0  1  0  0  0  0  0  0  0  0  0
   -8.2389    0.0305   -1.6360 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8685   -0.8814   -2.5391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8771   -1.7827   -2.7029 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9021   -1.4352   -1.8908 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.1429   -1.9837   -1.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.6046   -3.1468   -2.3140 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9418   -1.3785   -0.7689 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5461   -0.2551   -0.1086 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3360    0.2453   -0.3604 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4749   -0.3089   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2260    0.9984    0.3653 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.2721    0.9618    1.2136 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2636    2.1624    0.5307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.8215    3.3452    0.7690 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5988    4.0896    2.2166 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1280    4.0109    2.5724 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4169    3.3186    3.5026 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0308    5.6997    2.2732 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8590    2.5214    4.2100 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5929    3.1209    2.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.4716    4.1996    3.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7690    2.0471    3.1537 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0790    3.4268    0.7847 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6409    2.0065   -1.4344 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5529    2.1913   -3.0159 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9852   -0.1236   -2.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7739    0.0385   -2.4398 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4278   -0.8306   -0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6849   -2.0126    1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8111   -0.4459    1.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3446   -0.0982    1.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7599   -1.5229    2.7151 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5279   -2.2549   -0.1149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1264   -4.1632    0.2863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9515   -2.2368   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8052   -2.5286    1.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4541   -4.2266    1.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1319   -3.7555    0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5322   -4.9963   -0.8537 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6013   -3.8464   -2.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0013   -4.0804   -1.3934 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1313   -1.8843   -0.9942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3714   -1.5806   -1.8863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1219    2.0405    0.1288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021   -1.3993    0.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7078    0.1359   -0.0115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6344    1.4772    0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0764    2.8834   -1.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1171    2.1368   -1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9082   -0.8708   -3.0405 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8954   -3.7515   -2.7946 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.5980   -3.4437   -2.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1894    0.2216    0.5966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6727    0.0151    0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9591    0.8667    2.1302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6145    1.8694    1.3736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3987    3.2893    3.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8189    5.9086    2.8396 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 19 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 24 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 28 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 40 42  1  0
 42 43  2  0
 43 44  1  0
 44 45  2  0
 35 46  1  0
 46 47  1  0
 46 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  2  0
 50 52  1  0
 50 53  1  0
 48 33  1  0
 45 36  1  0
 45 39  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  0
  3 58  1  0
  7 59  1  0
  7 60  1  0
  8 61  1  0
  8 62  1  0
  9 63  1  0
 12 64  1  0
 12 65  1  0
 13 66  1  0
 13 67  1  0
 14 68  1  0
 17 69  1  1
 18 70  1  0
 20 71  1  0
 20 72  1  0
 20 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 26 79  1  0
 30 80  1  0
 32 81  1  0
 32 82  1  0
 33 83  1  6
 35 84  1  1
 37 85  1  0
 41 86  1  0
 41 87  1  0
 43 88  1  0
 46 89  1  6
 47 90  1  0
 48 91  1  1
 52 92  1  0
 53 93  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Crotonyl-CoA	ChEBI
trans-But-2-enoyl-CoA	ChEBI
trans-Butyr-2-enoyl-CoA	ChEBI
2-Butenoyl-CoA	Kegg
But-2-enoyl-CoA	Kegg
(2E)-But-2-enoyl-CoA	Kegg
Crotonyl-coenzyme A	HMDB
(e)-But-2-enoyl-CoA	ChEBI
Crotonoyl-CoA	HMDB
Crotonoyl-coenzyme A	HMDB
Crotonyl coenzyme A	HMDB
trans-2-Butenoyl-CoA	HMDB
trans-2-Butenoyl-coenzyme A	HMDB
trans-Crotonoyl-CoA	HMDB
trans-Crotonoyl-coenzyme A	HMDB
trans-Crotonyl CoA	HMDB

Chemical Formula

C₂₅H₄₀N₇O₁₇P₃S

Average Molecular Weight

835.608

Monoisotopic Molecular Weight

835.141423115

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-2-hydroxy-3,3-dimethylbutanimidic acid

CAS Registry Number

38795-21-0

SMILES

C\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/b5-4+/t14-,18-,19-,20+,24-/m1/s1

InChI Key

KFWWCMJSYSSPSK-PAXLJYGASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

but-2-enoyl-CoA (CHEBI:15473 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0002009)
Peroxisome (HMDB: HMDB0002009)

Organ

Liver (HMDB: HMDB0002009)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0002009)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0002009)

Source

Endogenous

Endogenous (HMDB: HMDB0002009)

Animal

Animal (HMDB: HMDB0002009)

Exogenous

Food

Food (HMDB: HMDB0002009)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Exogenous (HMDB: HMDB0002009)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0002009)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0002009)
Fatty Acid Metabolism (PathBank: SMP0063589)
Fatty Acid Metabolism (PathBank: SMP0002361)
Butyrate Metabolism (PathBank: SMP0063603)
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids (PathBank: SMP0087265)
Lysine Degradation (PathBank: SMP0087300)
Lysine Metabolism (PathBank: SMP0002434)
Fatty Acid Oxidation (Butanoate) (PathBank: SMP0121346)

Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD) (PathBank: SMP0120632)
Lipid metabolism pathway (HMDB: HMDB0002009)

Disease pathway

Pyridoxine Dependency with Seizures (PathBank: SMP0120635)
Glutaric Aciduria Type I (PathBank: SMP0120704)
Very-Long-Chain Acyl-CoA Dehydrogenase Deficiency (VLCAD) (PathBank: SMP0120824)
Carnitine Palmitoyl Transferase Deficiency II (PathBank: SMP0120825)
Ethylmalonic Encephalopathy (HMDB: HMDB0002009)
Trifunctional Protein Deficiency (PathBank: SMP0120609)
Ethylmalonic Encephalopathy (PathBank: SMP0120696)
Hyperlysinemia I, Familial (PathBank: SMP0120811)
Hyperlysinemia II or Saccharopinuria (PathBank: SMP0120812)
Carnitine Palmitoyl Transferase Deficiency I (PathBank: SMP0120822)
2-Aminoadipic 2-Oxoadipic Aciduria (PathBank: SMP0120870)
Long Chain Acyl-CoA Dehydrogenase Deficiency (LCAD) (PathBank: SMP0120604)
Medium Chain Acyl-CoA Dehydrogenase Deficiency (MCAD) (PathBank: SMP0120607)
Short-Chain Acyl-CoA Dehydrogenase Deficiency (SCAD Deficiency) (PathBank: SMP0120740)
Saccharopinuria/Hyperlysinemia II (PathBank: SMP0120746)
Short-Chain 3-Hydroxyacyl-CoA Dehydrogenase Deficiency (HADH) (PathBank: SMP0000568)

Cellular process

Cell signaling (HMDB: HMDB0002009)

Biochemical process

Lipid transport (HMDB: HMDB0002009)

Role

Biological role

Energy source (HMDB: HMDB0002009)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0002009)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.67 g/L	ALOGPS
logP	0.03	ALOGPS
logP	-4.2	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.43	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	370.61 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	183.57 m³·mol⁻¹	ChemAxon
Polarizability	75.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	205.325	30932474
DeepCCS	[M-H]-	203.672	30932474
DeepCCS	[M-2H]-	238.099	30932474
DeepCCS	[M+Na]+	212.813	30932474
AllCCS	[M+H]+	256.2	32859911
AllCCS	[M+H-H2O]+	256.5	32859911
AllCCS	[M+NH4]+	255.9	32859911
AllCCS	[M+Na]+	255.8	32859911
AllCCS	[M-H]-	250.7	32859911
AllCCS	[M+Na-2H]-	254.8	32859911
AllCCS	[M+HCOO]-	259.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.53 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3137 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.25 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	516.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1270.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	169.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	162.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	365.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	422.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	822.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	664.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	302.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	677.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	225.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	470.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	358.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	331.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Crotonoyl-CoA	C\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	6290.3	Standard polar	33892256
Crotonoyl-CoA	C\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	4225.1	Standard non polar	33892256
Crotonoyl-CoA	C\C=C\C(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N	6490.0	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 10V, Positive-QTOF	splash10-00kr-1921000110-de694ebfa0837735d1be	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 20V, Positive-QTOF	splash10-000l-1911000000-5b106b3a07df5c8c3755	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 40V, Positive-QTOF	splash10-000i-1920000000-2ecd1925643a7cc3e17f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 10V, Negative-QTOF	splash10-00lr-7920142560-10f7deae9d59f3fd3b6d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 20V, Negative-QTOF	splash10-001i-6910110000-fc85ca4055cec31805dc	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 40V, Negative-QTOF	splash10-057i-5900100000-a22910037b80042e1f67	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 10V, Negative-QTOF	splash10-053r-0000000090-ab823464181bc32f03d2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 20V, Negative-QTOF	splash10-001i-9100102220-fd6f03390bd7a43d01c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 40V, Negative-QTOF	splash10-0170-5003512900-74bcb83a0ff12e7c4a9b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 10V, Positive-QTOF	splash10-000i-0000000190-99bf5276fb1e28f0a070	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 20V, Positive-QTOF	splash10-000i-0901002270-22f1df5d925d91d4db45	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Crotonoyl-CoA 40V, Positive-QTOF	splash10-004i-0219000000-59474207fbf5193eca0d	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Liver

Pathways

Name	SMPDB/PathBank	KEGG
Lysine degradation	Not Available
Butyrate Metabolism
Fatty acid Metabolism
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available
Ethylmalonic Encephalopathy		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022792

KNApSAcK ID

Not Available

Chemspider ID

4593713

KEGG Compound ID

C00877

BioCyc ID

CROTONYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5497143

PDB ID

Not Available

ChEBI ID

15473

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Fu Z, Wang M, Paschke R, Rao KS, Frerman FE, Kim JJ: Crystal structures of human glutaryl-CoA dehydrogenase with and without an alternate substrate: structural bases of dehydrogenation and decarboxylation reactions. Biochemistry. 2004 Aug 3;43(30):9674-84. [PubMed:15274622 ]
Rozen R, Vockley J, Zhou L, Milos R, Willard J, Fu K, Vicanek C, Low-Nang L, Torban E, Fournier B: Isolation and expression of a cDNA encoding the precursor for a novel member (ACADSB) of the acyl-CoA dehydrogenase gene family. Genomics. 1994 Nov 15;24(2):280-7. [PubMed:7698750 ]
Hyman DB, Tanaka K: Specific glutaryl-CoA dehydrogenating activity is deficient in cultured fibroblasts from glutaric aciduria patients. J Clin Invest. 1984 Mar;73(3):778-84. [PubMed:6423663 ]
Kalousek F, Darigo MD, Rosenberg LE: Isolation and characterization of propionyl-CoA carboxylase from normal human liver. Evidence for a protomeric tetramer of nonidentical subunits. J Biol Chem. 1980 Jan 10;255(1):60-5. [PubMed:6765947 ]
Dwyer TM, Rao KS, Westover JB, Kim JJ, Frerman FE: The function of Arg-94 in the oxidation and decarboxylation of glutaryl-CoA by human glutaryl-CoA dehydrogenase. J Biol Chem. 2001 Jan 5;276(1):133-8. [PubMed:11024031 ]
Babidge W, Millard S, Roediger W: Sulfides impair short chain fatty acid beta-oxidation at acyl-CoA dehydrogenase level in colonocytes: implications for ulcerative colitis. Mol Cell Biochem. 1998 Apr;181(1-2):117-24. [PubMed:9562248 ]
Lenich AC, Goodman SI: The purification and characterization of glutaryl-coenzyme A dehydrogenase from porcine and human liver. J Biol Chem. 1986 Mar 25;261(9):4090-6. [PubMed:3081514 ]
Gregersen N, Brandt NJ, Christensen E, Gron I, Rasmussen K, Brandt S: Glutaric aciduria: clinical and laboratory findings in two brothers. J Pediatr. 1977 May;90(5):740-5. [PubMed:853337 ]
Hodgins MB: Possible mechanisms of androgen resistance in 5 alpha-reductase deficiency: implications for the physiological roles of 5 alpha-reductases. J Steroid Biochem. 1983 Jul;19(1B):555-9. [PubMed:6887883 ]
Saenger AK, Nguyen TV, Vockley J, Stankovich MT: Thermodynamic regulation of human short-chain acyl-CoA dehydrogenase by substrate and product binding. Biochemistry. 2005 Dec 13;44(49):16043-53. [PubMed:16331964 ]
Finocchiaro G, Ito M, Tanaka K: Purification and properties of short chain acyl-CoA, medium chain acyl-CoA, and isovaleryl-CoA dehydrogenases from human liver. J Biol Chem. 1987 Jun 15;262(17):7982-9. [PubMed:3597357 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 114 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Enzyme Details

2. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Enzyme Details

3. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Enzyme Details

6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Reactions

Butyryl-CoA + electron-transfer flavoprotein → Crotonoyl-CoA + reduced electron-transfer flavoprotein	details
Butyryl-CoA + NAD → Crotonoyl-CoA + NADH + Hydrogen Ion	details
Butyryl-CoA + FAD → FADH + Crotonoyl-CoA	details

Enzyme Details

7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Butyryl-CoA + FAD → FADH + Crotonoyl-CoA	details

Enzyme Details

8. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Reactions

Butyryl-CoA + FAD → FADH + Crotonoyl-CoA	details

Enzyme Details

9. Peroxisomal acyl-coenzyme A oxidase 2

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:: ACOX2
Uniprot ID:: Q99424
Molecular weight:: 76826.14

Enzyme Details

10. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 114 proteins in total.

Show all enzymes and transporters

Showing metabocard for Crotonoyl-CoA (HMDB0002009)

MOL for HMDB0002009 (Crotonoyl-CoA)

3D MOL for HMDB0002009 (Crotonoyl-CoA)

3D SDF for HMDB0002009 (Crotonoyl-CoA)

3D-SDF for HMDB0002009 (Crotonoyl-CoA)

PDB for HMDB0002009 (Crotonoyl-CoA)

3D PDB for HMDB0002009 (Crotonoyl-CoA)

SMILES for HMDB0002009 (Crotonoyl-CoA)

INCHI for HMDB0002009 (Crotonoyl-CoA)

Structure for HMDB0002009 (Crotonoyl-CoA)

3D Structure for HMDB0002009 (Crotonoyl-CoA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions

Reactions

Transporters