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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2022-03-07 02:49:08 UTC

HMDB ID

HMDB0001052

Secondary Accession Numbers

HMDB01052

Metabolite Identification

Common Name

(S)-3-Hydroxyisobutyryl-CoA

Description

(S)-3-Hydroxyisobutyryl-CoA is s metabolite of 3-hydroxyisobutyryl-CoA hydrolase (EC 3.1.2.4 ) during beta-alanine metabolism (KEGG 00410), propanoate metabolism (KEGG 00640), and valine, leucine and isoleucine degradation (KEGG 00280). Deficiencies of this enzyme in valine degradation can result in hypotonia, poor feeding, motor delay, and subsequent neurological regression in infancy, episodes of ketoacidosis and Leigh-like changes in the basal ganglia on a magnetic resonance imaging scan (PMID 17160907 ).

Structure

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


  Mrv1652309042000172D          

 54 56  0  0  0  0            999 V2000
   26.0583  -17.7878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7810  -17.4565    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554  -18.4792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.7767  -18.3324    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2642  -19.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279  -18.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704  -19.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6870  -18.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3341  -16.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688  -16.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0237  -17.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5299  -18.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3932  -18.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8391  -19.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7892  -19.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8716  -17.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1136  -17.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4399  -19.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2878  -17.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1307  -17.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -18.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9011  -17.4939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -20.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -22.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -20.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -22.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -23.2867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1258  -18.7123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9686  -18.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4814  -18.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9954  -19.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2656  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4791  -20.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9340  -18.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7044  -21.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -22.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9512  -18.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7044  -18.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1982  -18.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -22.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2882  -17.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6144  -19.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3727  -18.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7941  -18.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5472  -18.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2155  -18.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6368  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3900  -18.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4797  -17.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8114  -18.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2328  -17.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3949  -16.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 50  1  0  0  0  0
  1 52  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 34  1  0  0  0  0
 12 40  1  0  0  0  0
 15 39  1  0  0  0  0
 19 45  2  0  0  0  0
 20 48  2  0  0  0  0
 21 52  2  0  0  0  0
 22 53  1  0  0  0  0
 23 33  1  0  0  0  0
 23 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
 25 35  2  0  0  0  0
 25 44  1  0  0  0  0
 26 41  1  0  0  0  0
 26 44  2  0  0  0  0
 27 41  1  0  0  0  0
 28 45  1  0  0  0  0
 28 46  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 35 37  1  0  0  0  0
 37 41  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
 38 43  1  0  0  0  0
 39 45  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
M  END

HMDB0001052
     RDKit          3D
(S)-3-Hydroxyisobutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   13.8847    0.6014   -2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6710   -0.2779   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8091   -0.1240    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639    1.1868    0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354   -0.0669   -0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6524   -1.0596    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6772    1.5375    0.1706 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0295    1.3758    0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1191    0.7423   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7820    0.5800    0.3533 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8020   -0.0325   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -0.4625   -1.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3971   -0.2042    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -1.1350   -0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -1.4006   -0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -1.9734    0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -2.2213    1.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -2.3183    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -2.5394    2.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.5377    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -1.5543   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314   -2.1765    1.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -0.0942    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    0.4682    1.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    2.0806    1.5339 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0119    2.9680    0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408    2.2568    3.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    2.4909    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    1.0912    1.3060 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1348    0.2121    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    0.1907   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    1.4586    1.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6212    0.3656    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0729    0.6538    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7828   -0.3684   -0.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4116    0.0932   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6531   -0.6111   -1.6159 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5043   -0.3290   -2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5654   -1.1751   -2.5731 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4019   -1.9980   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1848   -3.0232   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4159   -3.4269   -1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7375   -3.6825    0.0256 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5569   -3.3250    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7837   -2.3248    0.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1968   -1.6368   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6376    1.5672   -1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6227    1.6587   -0.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2920    1.8963   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3930    3.0638    0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4772    4.2523   -0.4472 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1959    5.4061    0.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474    4.8378   -1.7869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    3.6586   -1.0190 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9316    0.8462   -2.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5025    0.0409   -2.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4254    1.5334   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7221   -1.3333   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7600   -0.8209    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7419   -0.3628   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3685    1.2252    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373    2.3766    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0799    0.7544    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4945   -0.2847   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1138    1.3965   -1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5503    0.9228    1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -0.5059    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9054    0.8136   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -0.7518   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217   -2.1186   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -1.1230   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641   -3.4066    0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -1.6621    3.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615   -2.3615   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -1.8028   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287   -0.5980   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -3.2589    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.7053    2.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824   -2.0321    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    0.4756    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -0.1161    2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    3.2017    3.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514   -0.6563   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1723    0.3797   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963   -0.5935    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5225    0.8477    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8110    0.0446   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3315    0.4611   -3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2046   -3.7850   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5518   -3.3731   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2010   -3.8593    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8008    2.1728   -1.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2563    2.0310    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884    2.0127   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3669    5.8398   -1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0137    3.5206   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 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  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  3 59  1  0
  3 60  1  0
  4 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  0
 13 67  1  0
 13 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  0
 18 72  1  0
 19 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 27 82  1  0
 31 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 36 87  1  0
 38 88  1  0
 42 89  1  0
 42 90  1  0
 44 91  1  0
 47 92  1  0
 48 93  1  0
 49 94  1  0
 53 95  1  0
 54 96  1  0
M  END


  Mrv1652309042000172D          

 54 56  0  0  0  0            999 V2000
   26.0583  -17.7878    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.7810  -17.4565    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   15.3554  -18.4792    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.7767  -18.3324    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.2642  -19.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2279  -18.0685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1704  -19.5188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6870  -18.9630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3341  -16.8443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1688  -16.9033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0237  -17.9955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5299  -18.6692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3932  -18.0096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8391  -19.1476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7892  -19.6798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8716  -17.8110    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1136  -17.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4399  -19.0855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2878  -17.5548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1307  -17.2609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8962  -18.9453    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9011  -17.4939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -20.9728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2229  -22.3006    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -20.8116    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -22.0492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -23.2867    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1258  -18.7123    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9686  -18.4184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4814  -18.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9954  -19.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2656  -19.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4791  -20.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9340  -18.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7044  -21.6367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4423  -22.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9512  -18.5223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7044  -18.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1982  -18.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7277  -22.4617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2882  -17.7692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6144  -19.2755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0132  -21.2242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3727  -18.3755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7941  -18.2285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5472  -18.5654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2155  -18.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6368  -17.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3900  -18.2716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4797  -17.6409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8114  -18.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2328  -17.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3949  -16.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 50  1  0  0  0  0
  1 52  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 32  1  0  0  0  0
  5 33  1  0  0  0  0
  6 30  1  0  0  0  0
  7 31  1  0  0  0  0
  8 34  1  0  0  0  0
 12 40  1  0  0  0  0
 15 39  1  0  0  0  0
 19 45  2  0  0  0  0
 20 48  2  0  0  0  0
 21 52  2  0  0  0  0
 22 53  1  0  0  0  0
 23 33  1  0  0  0  0
 23 35  1  0  0  0  0
 23 36  1  0  0  0  0
 24 36  2  0  0  0  0
 24 37  1  0  0  0  0
 25 35  2  0  0  0  0
 25 44  1  0  0  0  0
 26 41  1  0  0  0  0
 26 44  2  0  0  0  0
 27 41  1  0  0  0  0
 28 45  1  0  0  0  0
 28 46  1  0  0  0  0
 29 48  1  0  0  0  0
 29 49  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  0  0  0  0
 32 34  1  0  0  0  0
 35 37  1  0  0  0  0
 37 41  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
 38 43  1  0  0  0  0
 39 45  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 49 50  1  0  0  0  0
 51 52  1  0  0  0  0
 51 53  1  0  0  0  0
 51 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0001052

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)

> <INCHI_KEY>
WWEOGFZEFHPUAM-UHFFFAOYSA-N

> <FORMULA>
C25H42N7O18P3S

> <MOLECULAR_WEIGHT>
853.623

> <EXACT_MASS>
853.151987801

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
75.70314825666493

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.56

> <JCHEM_LOGP>
-5.918868144481294

> <ALOGPS_LOGS>
-2.31

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398193

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.8599999999999

> <JCHEM_REFRACTIVITY>
183.18410000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.14e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001052
     RDKit          3D
(S)-3-Hydroxyisobutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   13.8847    0.6014   -2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6710   -0.2779   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8091   -0.1240    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639    1.1868    0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354   -0.0669   -0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6524   -1.0596    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6772    1.5375    0.1706 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0295    1.3758    0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1191    0.7423   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7820    0.5800    0.3533 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8020   -0.0325   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -0.4625   -1.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3971   -0.2042    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -1.1350   -0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -1.4006   -0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -1.9734    0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -2.2213    1.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -2.3183    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -2.5394    2.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.5377    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -1.5543   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314   -2.1765    1.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -0.0942    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    0.4682    1.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    2.0806    1.5339 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0119    2.9680    0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408    2.2568    3.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    2.4909    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    1.0912    1.3060 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1348    0.2121    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    0.1907   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    1.4586    1.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6212    0.3656    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0729    0.6538    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7828   -0.3684   -0.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4116    0.0932   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6531   -0.6111   -1.6159 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5043   -0.3290   -2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5654   -1.1751   -2.5731 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4019   -1.9980   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1848   -3.0232   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4159   -3.4269   -1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7375   -3.6825    0.0256 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5569   -3.3250    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7837   -2.3248    0.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1968   -1.6368   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6376    1.5672   -1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6227    1.6587   -0.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2920    1.8963   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3930    3.0638    0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4772    4.2523   -0.4472 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1959    5.4061    0.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474    4.8378   -1.7869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    3.6586   -1.0190 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9316    0.8462   -2.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5025    0.0409   -2.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4254    1.5334   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7221   -1.3333   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7600   -0.8209    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7419   -0.3628   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3685    1.2252    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373    2.3766    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0799    0.7544    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4945   -0.2847   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1138    1.3965   -1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5503    0.9228    1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -0.5059    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9054    0.8136   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -0.7518   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217   -2.1186   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -1.1230   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641   -3.4066    0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -1.6621    3.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615   -2.3615   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -1.8028   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287   -0.5980   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -3.2589    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.7053    2.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824   -2.0321    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    0.4756    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -0.1161    2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    3.2017    3.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514   -0.6563   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1723    0.3797   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963   -0.5935    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5225    0.8477    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8110    0.0446   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3315    0.4611   -3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2046   -3.7850   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.8008    2.1728   -1.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2563    2.0310    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884    2.0127   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3669    5.8398   -1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0137    3.5206   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
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 54 96  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  S   UNK     0      48.642 -33.204   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      23.858 -32.585   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      28.663 -34.495   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      31.317 -34.220   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      24.760 -37.212   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      22.825 -33.728   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      20.851 -36.435   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      27.416 -35.398   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      24.890 -31.443   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      22.715 -31.553   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      29.911 -33.592   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      32.722 -34.849   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      25.001 -33.618   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      29.566 -35.742   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      36.940 -36.736   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      27.760 -33.247   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      31.945 -32.815   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      30.688 -35.626   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      37.871 -32.769   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      43.177 -32.220   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      50.206 -35.365   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      53.949 -32.655   0.000  0.00  0.00           O+0
HETATM   23  N   UNK     0      22.816 -39.149   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      22.816 -41.628   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      20.025 -38.848   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      18.691 -41.159   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      20.025 -43.469   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      39.435 -34.930   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0      44.741 -34.381   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0      23.299 -35.193   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.391 -36.438   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      24.762 -35.672   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      23.294 -37.685   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.010 -34.769   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      21.359 -39.619   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      23.715 -40.389   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      21.359 -41.159   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      35.376 -34.575   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      36.782 -35.204   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      33.970 -33.946   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      20.025 -41.929   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      36.005 -33.169   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      34.747 -35.981   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.691 -39.619   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      38.029 -34.301   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      40.682 -34.027   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      42.088 -34.655   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      43.336 -33.752   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      45.989 -33.478   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      47.395 -34.107   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      51.295 -32.930   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      50.048 -33.833   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      52.701 -33.558   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      51.137 -31.398   0.000  0.00  0.00           C+0
CONECT    1   50   52                                                       
CONECT    2    6    9   10   13                                             
CONECT    3    8   11   14   16                                             
CONECT    4   11   12   17   18                                             
CONECT    5   32   33                                                       
CONECT    6    2   30                                                       
CONECT    7   31                                                            
CONECT    8    3   34                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    4   40                                                       
CONECT   13    2                                                            
CONECT   14    3                                                            
CONECT   15   39                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   45                                                            
CONECT   20   48                                                            
CONECT   21   52                                                            
CONECT   22   53                                                            
CONECT   23   33   35   36                                                  
CONECT   24   36   37                                                       
CONECT   25   35   44                                                       
CONECT   26   41   44                                                       
CONECT   27   41                                                            
CONECT   28   45   46                                                       
CONECT   29   48   49                                                       
CONECT   30    6   31   32                                                  
CONECT   31    7   30   33                                                  
CONECT   32    5   30   34                                                  
CONECT   33    5   23   31                                                  
CONECT   34    8   32                                                       
CONECT   35   23   25   37                                                  
CONECT   36   23   24                                                       
CONECT   37   24   35   41                                                  
CONECT   38   39   40   42   43                                             
CONECT   39   15   38   45                                                  
CONECT   40   12   38                                                       
CONECT   41   26   27   37                                                  
CONECT   42   38                                                            
CONECT   43   38                                                            
CONECT   44   25   26                                                       
CONECT   45   19   28   39                                                  
CONECT   46   28   47                                                       
CONECT   47   46   48                                                       
CONECT   48   20   29   47                                                  
CONECT   49   29   50                                                       
CONECT   50    1   49                                                       
CONECT   51   52   53   54                                                  
CONECT   52    1   21   51                                                  
CONECT   53   22   51                                                       
CONECT   54   51                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

COMPND    HMDB0001052
HETATM    1  C1  UNL     1      13.885   0.601  -2.004  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.671  -0.278  -0.791  1.00  0.00           C  
HETATM    3  C3  UNL     1      14.809  -0.124   0.164  1.00  0.00           C  
HETATM    4  O1  UNL     1      14.964   1.187   0.626  1.00  0.00           O  
HETATM    5  C4  UNL     1      12.335  -0.067  -0.196  1.00  0.00           C  
HETATM    6  O2  UNL     1      11.652  -1.060   0.056  1.00  0.00           O  
HETATM    7  S1  UNL     1      11.677   1.537   0.171  1.00  0.00           S  
HETATM    8  C5  UNL     1      10.029   1.376   0.902  1.00  0.00           C  
HETATM    9  C6  UNL     1       9.119   0.742  -0.138  1.00  0.00           C  
HETATM   10  N1  UNL     1       7.782   0.580   0.353  1.00  0.00           N  
HETATM   11  C7  UNL     1       6.802  -0.032  -0.437  1.00  0.00           C  
HETATM   12  O3  UNL     1       7.088  -0.462  -1.609  1.00  0.00           O  
HETATM   13  C8  UNL     1       5.397  -0.204   0.072  1.00  0.00           C  
HETATM   14  C9  UNL     1       4.681  -1.135  -0.854  1.00  0.00           C  
HETATM   15  N2  UNL     1       3.291  -1.401  -0.466  1.00  0.00           N  
HETATM   16  C10 UNL     1       3.030  -1.973   0.777  1.00  0.00           C  
HETATM   17  O4  UNL     1       4.047  -2.221   1.528  1.00  0.00           O  
HETATM   18  C11 UNL     1       1.728  -2.318   1.312  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.849  -2.539   2.716  1.00  0.00           O  
HETATM   20  C12 UNL     1       0.525  -1.538   0.987  1.00  0.00           C  
HETATM   21  C13 UNL     1       0.161  -1.554  -0.460  1.00  0.00           C  
HETATM   22  C14 UNL     1      -0.631  -2.176   1.790  1.00  0.00           C  
HETATM   23  C15 UNL     1       0.571  -0.094   1.491  1.00  0.00           C  
HETATM   24  O6  UNL     1      -0.655   0.468   1.076  1.00  0.00           O  
HETATM   25  P1  UNL     1      -0.802   2.081   1.534  1.00  0.00           P  
HETATM   26  O7  UNL     1       0.012   2.968   0.615  1.00  0.00           O  
HETATM   27  O8  UNL     1      -0.241   2.257   3.114  1.00  0.00           O  
HETATM   28  O9  UNL     1      -2.465   2.491   1.477  1.00  0.00           O  
HETATM   29  P2  UNL     1      -3.359   1.091   1.306  1.00  0.00           P  
HETATM   30  O10 UNL     1      -3.135   0.212   2.503  1.00  0.00           O  
HETATM   31  O11 UNL     1      -2.905   0.191  -0.066  1.00  0.00           O  
HETATM   32  O12 UNL     1      -5.007   1.459   1.147  1.00  0.00           O  
HETATM   33  C16 UNL     1      -5.621   0.366   0.504  1.00  0.00           C  
HETATM   34  C17 UNL     1      -7.073   0.654   0.363  1.00  0.00           C  
HETATM   35  O13 UNL     1      -7.783  -0.368  -0.247  1.00  0.00           O  
HETATM   36  C18 UNL     1      -8.412   0.093  -1.368  1.00  0.00           C  
HETATM   37  N3  UNL     1      -9.653  -0.611  -1.616  1.00  0.00           N  
HETATM   38  C19 UNL     1     -10.504  -0.329  -2.626  1.00  0.00           C  
HETATM   39  N4  UNL     1     -11.565  -1.175  -2.573  1.00  0.00           N  
HETATM   40  C20 UNL     1     -11.402  -1.998  -1.538  1.00  0.00           C  
HETATM   41  C21 UNL     1     -12.185  -3.023  -1.062  1.00  0.00           C  
HETATM   42  N5  UNL     1     -13.416  -3.427  -1.634  1.00  0.00           N  
HETATM   43  N6  UNL     1     -11.738  -3.683   0.026  1.00  0.00           N  
HETATM   44  C22 UNL     1     -10.557  -3.325   0.608  1.00  0.00           C  
HETATM   45  N7  UNL     1      -9.784  -2.325   0.152  1.00  0.00           N  
HETATM   46  C23 UNL     1     -10.197  -1.637  -0.940  1.00  0.00           C  
HETATM   47  C24 UNL     1      -8.638   1.567  -1.087  1.00  0.00           C  
HETATM   48  O14 UNL     1      -9.623   1.659  -0.130  1.00  0.00           O  
HETATM   49  C25 UNL     1      -7.292   1.896  -0.428  1.00  0.00           C  
HETATM   50  O15 UNL     1      -7.393   3.064   0.324  1.00  0.00           O  
HETATM   51  P3  UNL     1      -6.477   4.252  -0.447  1.00  0.00           P  
HETATM   52  O16 UNL     1      -6.196   5.406   0.490  1.00  0.00           O  
HETATM   53  O17 UNL     1      -7.347   4.838  -1.787  1.00  0.00           O  
HETATM   54  O18 UNL     1      -5.007   3.659  -1.019  1.00  0.00           O  
HETATM   55  H1  UNL     1      12.932   0.846  -2.529  1.00  0.00           H  
HETATM   56  H2  UNL     1      14.503   0.041  -2.731  1.00  0.00           H  
HETATM   57  H3  UNL     1      14.425   1.533  -1.674  1.00  0.00           H  
HETATM   58  H4  UNL     1      13.722  -1.333  -1.181  1.00  0.00           H  
HETATM   59  H5  UNL     1      14.760  -0.821   1.031  1.00  0.00           H  
HETATM   60  H6  UNL     1      15.742  -0.363  -0.431  1.00  0.00           H  
HETATM   61  H7  UNL     1      15.368   1.225   1.533  1.00  0.00           H  
HETATM   62  H8  UNL     1       9.637   2.377   1.199  1.00  0.00           H  
HETATM   63  H9  UNL     1      10.080   0.754   1.818  1.00  0.00           H  
HETATM   64  H10 UNL     1       9.495  -0.285  -0.368  1.00  0.00           H  
HETATM   65  H11 UNL     1       9.114   1.396  -1.032  1.00  0.00           H  
HETATM   66  H12 UNL     1       7.550   0.923   1.307  1.00  0.00           H  
HETATM   67  H13 UNL     1       5.425  -0.506   1.107  1.00  0.00           H  
HETATM   68  H14 UNL     1       4.905   0.814  -0.005  1.00  0.00           H  
HETATM   69  H15 UNL     1       4.726  -0.752  -1.898  1.00  0.00           H  
HETATM   70  H16 UNL     1       5.222  -2.119  -0.863  1.00  0.00           H  
HETATM   71  H17 UNL     1       2.555  -1.123  -1.181  1.00  0.00           H  
HETATM   72  H18 UNL     1       1.464  -3.407   0.961  1.00  0.00           H  
HETATM   73  H19 UNL     1       1.838  -1.662   3.196  1.00  0.00           H  
HETATM   74  H20 UNL     1       0.661  -2.362  -1.016  1.00  0.00           H  
HETATM   75  H21 UNL     1      -0.962  -1.803  -0.564  1.00  0.00           H  
HETATM   76  H22 UNL     1       0.329  -0.598  -0.961  1.00  0.00           H  
HETATM   77  H23 UNL     1      -0.416  -3.259   1.912  1.00  0.00           H  
HETATM   78  H24 UNL     1      -0.648  -1.705   2.792  1.00  0.00           H  
HETATM   79  H25 UNL     1      -1.582  -2.032   1.248  1.00  0.00           H  
HETATM   80  H26 UNL     1       1.420   0.476   1.116  1.00  0.00           H  
HETATM   81  H27 UNL     1       0.534  -0.116   2.598  1.00  0.00           H  
HETATM   82  H28 UNL     1      -0.174   3.202   3.388  1.00  0.00           H  
HETATM   83  H29 UNL     1      -3.451  -0.656  -0.010  1.00  0.00           H  
HETATM   84  H30 UNL     1      -5.172   0.380  -0.534  1.00  0.00           H  
HETATM   85  H31 UNL     1      -5.396  -0.594   1.024  1.00  0.00           H  
HETATM   86  H32 UNL     1      -7.522   0.848   1.377  1.00  0.00           H  
HETATM   87  H33 UNL     1      -7.811   0.045  -2.304  1.00  0.00           H  
HETATM   88  H34 UNL     1     -10.332   0.461  -3.350  1.00  0.00           H  
HETATM   89  H35 UNL     1     -14.205  -3.785  -1.051  1.00  0.00           H  
HETATM   90  H36 UNL     1     -13.552  -3.373  -2.655  1.00  0.00           H  
HETATM   91  H37 UNL     1     -10.201  -3.859   1.484  1.00  0.00           H  
HETATM   92  H38 UNL     1      -8.801   2.173  -1.986  1.00  0.00           H  
HETATM   93  H39 UNL     1      -9.256   2.031   0.709  1.00  0.00           H  
HETATM   94  H40 UNL     1      -6.588   2.013  -1.274  1.00  0.00           H  
HETATM   95  H41 UNL     1      -7.367   5.840  -1.786  1.00  0.00           H  
HETATM   96  H42 UNL     1      -5.014   3.521  -2.019  1.00  0.00           H  
CONECT    1    2   55   56   57
CONECT    2    3    5   58
CONECT    3    4   59   60
CONECT    4   61
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   62   63
CONECT    9   10   64   65
CONECT   10   11   66
CONECT   11   12   12   13
CONECT   13   14   67   68
CONECT   14   15   69   70
CONECT   15   16   71
CONECT   16   17   17   18
CONECT   18   19   20   72
CONECT   19   73
CONECT   20   21   22   23
CONECT   21   74   75   76
CONECT   22   77   78   79
CONECT   23   24   80   81
CONECT   24   25
CONECT   25   26   26   27   28
CONECT   27   82
CONECT   28   29
CONECT   29   30   30   31   32
CONECT   31   83
CONECT   32   33
CONECT   33   34   84   85
CONECT   34   35   49   86
CONECT   35   36
CONECT   36   37   47   87
CONECT   37   38   46
CONECT   38   39   39   88
CONECT   39   40
CONECT   40   41   41   46
CONECT   41   42   43
CONECT   42   89   90
CONECT   43   44   44
CONECT   44   45   91
CONECT   45   46   46
CONECT   47   48   49   92
CONECT   48   93
CONECT   49   50   94
CONECT   50   51
CONECT   51   52   52   53   54
CONECT   53   95
CONECT   54   96
END

HMDB0001052
     RDKit          3D
(S)-3-Hydroxyisobutyryl-CoA
 96 98  0  0  0  0  0  0  0  0999 V2000
   13.8847    0.6014   -2.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6710   -0.2779   -0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8091   -0.1240    0.1641 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639    1.1868    0.6264 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3354   -0.0669   -0.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6524   -1.0596    0.0556 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6772    1.5375    0.1706 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.0295    1.3758    0.9021 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1191    0.7423   -0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7820    0.5800    0.3533 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8020   -0.0325   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0881   -0.4625   -1.6087 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3971   -0.2042    0.0716 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6807   -1.1350   -0.8544 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2906   -1.4006   -0.4663 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0296   -1.9734    0.7772 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0467   -2.2213    1.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7282   -2.3183    1.3124 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -2.5394    2.7157 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5253   -1.5377    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609   -1.5543   -0.4595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6314   -2.1765    1.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -0.0942    1.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547    0.4682    1.0763 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8024    2.0806    1.5339 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.0119    2.9680    0.6149 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2408    2.2568    3.1143 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4649    2.4909    1.4767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3594    1.0912    1.3060 P   0  0  0  0  0  5  0  0  0  0  0  0
   -3.1348    0.2121    2.5033 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9049    0.1907   -0.0662 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0073    1.4586    1.1469 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6212    0.3656    0.5036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0729    0.6538    0.3634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7828   -0.3684   -0.2473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4116    0.0932   -1.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6531   -0.6111   -1.6159 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5043   -0.3290   -2.6256 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5654   -1.1751   -2.5731 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4019   -1.9980   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.1848   -3.0232   -1.0623 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4159   -3.4269   -1.6343 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.7375   -3.6825    0.0256 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5569   -3.3250    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7837   -2.3248    0.1525 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1968   -1.6368   -0.9404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6376    1.5672   -1.0872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6227    1.6587   -0.1302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2920    1.8963   -0.4279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3930    3.0638    0.3244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4772    4.2523   -0.4472 P   0  0  0  0  0  5  0  0  0  0  0  0
   -6.1959    5.4061    0.4903 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3474    4.8378   -1.7869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0068    3.6586   -1.0190 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9316    0.8462   -2.5294 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5025    0.0409   -2.7313 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4254    1.5334   -1.6738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.7221   -1.3333   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7600   -0.8209    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.7419   -0.3628   -0.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3685    1.2252    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373    2.3766    1.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0799    0.7544    1.8181 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4945   -0.2847   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1138    1.3965   -1.0320 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5503    0.9228    1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4248   -0.5059    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9054    0.8136   -0.0045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7265   -0.7518   -1.8981 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2217   -2.1186   -0.8633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5551   -1.1230   -1.1807 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641   -3.4066    0.9615 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -1.6621    3.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6615   -2.3615   -1.0156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619   -1.8028   -0.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3287   -0.5980   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4155   -3.2589    1.9120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6480   -1.7053    2.7920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5824   -2.0321    1.2480 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4200    0.4756    1.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5339   -0.1161    2.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1739    3.2017    3.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514   -0.6563   -0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1723    0.3797   -0.5342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3963   -0.5935    1.0242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5225    0.8477    1.3774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8110    0.0446   -2.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3315    0.4611   -3.3504 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.2046   -3.7850   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.5518   -3.3731   -2.6548 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2010   -3.8593    1.4839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8008    2.1728   -1.9865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2563    2.0310    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5884    2.0127   -1.2735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3669    5.8398   -1.7856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0137    3.5206   -2.0193 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 25 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 29 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  1  0
 38 39  2  0
 39 40  1  0
 40 41  2  0
 41 42  1  0
 41 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 36 47  1  0
 47 48  1  0
 47 49  1  0
 49 50  1  0
 50 51  1  0
 51 52  2  0
 51 53  1  0
 51 54  1  0
 49 34  1  0
 46 37  1  0
 46 40  1  0
  1 55  1  0
  1 56  1  0
  1 57  1  0
  2 58  1  0
  3 59  1  0
  3 60  1  0
  4 61  1  0
  8 62  1  0
  8 63  1  0
  9 64  1  0
  9 65  1  0
 10 66  1  0
 13 67  1  0
 13 68  1  0
 14 69  1  0
 14 70  1  0
 15 71  1  0
 18 72  1  0
 19 73  1  0
 21 74  1  0
 21 75  1  0
 21 76  1  0
 22 77  1  0
 22 78  1  0
 22 79  1  0
 23 80  1  0
 23 81  1  0
 27 82  1  0
 31 83  1  0
 33 84  1  0
 33 85  1  0
 34 86  1  0
 36 87  1  0
 38 88  1  0
 42 89  1  0
 42 90  1  0
 44 91  1  0
 47 92  1  0
 48 93  1  0
 49 94  1  0
 53 95  1  0
 54 96  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-3-Hydroxyisobutyryl-coenzyme A	HMDB
3-Hydroxy-2-methylpropanoyl-CoA	HMDB
3-Hydroxy-2-methylpropanoyl-coenzyme A	HMDB
3-Hydroxy-2-methylpropionyl-CoA	HMDB
3-Hydroxy-2-methylpropionyl-coenzyme A	HMDB
3-Hydroxy-isobutyryl-CoA	HMDB
3-Hydroxy-isobutyryl-coenzyme A	HMDB
3-Hydroxyisobutyryl-CoA	HMDB
3-Hydroxyisobutyryl-coenzyme A	HMDB

Chemical Formula

C₂₅H₄₂N₇O₁₈P₃S

Average Molecular Weight

853.623

Monoisotopic Molecular Weight

853.151987801

IUPAC Name

{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-3-{[2-({2-[(3-hydroxy-2-methylpropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

319440-43-2

SMILES

CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C25H42N7O18P3S/c1-13(8-33)24(38)54-7-6-27-15(34)4-5-28-22(37)19(36)25(2,3)10-47-53(44,45)50-52(42,43)46-9-14-18(49-51(39,40)41)17(35)23(48-14)32-12-31-16-20(26)29-11-30-21(16)32/h11-14,17-19,23,33,35-36H,4-10H2,1-3H3,(H,27,34)(H,28,37)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)

InChI Key

WWEOGFZEFHPUAM-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0001052)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001052)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001052)

Source

Endogenous

Endogenous (HMDB: HMDB0001052)

Animal

Animal (HMDB: HMDB0001052)

Exogenous

Food

Food (HMDB: HMDB0001052)

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)

Herb and spice mixture

Curry powder (FooDB: FOOD00678)

Vegetable

Cabbage

Onion-family vegetable

Root vegetable

Shoot vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)
Endive (FooDB: FOOD00048)
Rocket salad (ssp.) (FooDB: FOOD00077)
Swamp cabbage (FooDB: FOOD00091)
Lettuce (FooDB: FOOD00095)
Garden cress (FooDB: FOOD00099)
Spinach (FooDB: FOOD00178)
Swiss chard (FooDB: FOOD00237)
Chicory leaves (FooDB: FOOD00250)
Garland chrysanthemum (FooDB: FOOD00333)
Corn salad (FooDB: FOOD00340)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
Malabar spinach (FooDB: FOOD00404)
New Zealand spinach (FooDB: FOOD00415)
Yautia (FooDB: FOOD00510)
Ostrich fern (FooDB: FOOD00556)
Romaine lettuce (FooDB: FOOD00888)
Iceberg lettuce (FooDB: FOOD00973)
Pea shoots (FooDB: FOOD00975)
Yau choy (FooDB: FOOD00976)
Water spinach (FooDB: FOOD00977)

Fruit vegetable

Pepper (FooDB: FOOD00040)
Olive (FooDB: FOOD00121)
Avocado (FooDB: FOOD00130)
Garden tomato (FooDB: FOOD00171)
Cherry tomato (FooDB: FOOD00172)
Garden tomato (var.) (FooDB: FOOD00173)
Eggplant (FooDB: FOOD00174)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Groundcherry (FooDB: FOOD00371)
Pepper (C. frutescens) (FooDB: FOOD00428)
Mexican groundcherry (FooDB: FOOD00491)
Pepper (C. pubescens) (FooDB: FOOD00849)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Orange bell pepper (FooDB: FOOD00879)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Jalapeno pepper (FooDB: FOOD00955)
Cubanelle pepper (FooDB: FOOD00971)

Tuber

Stalk vegetable

Other vegetable

Giant butterbur (FooDB: FOOD00314)
Carob (FooDB: FOOD00321)
Chinese water chestnut (FooDB: FOOD00332)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Nopal (FooDB: FOOD00416)
Okra (FooDB: FOOD00420)
Sesbania flower (FooDB: FOOD00469)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Heart of palm (FooDB: FOOD00718)
Tree fern (FooDB: FOOD00797)

Mushroom

Castanospermum australe (FooDB: FOOD00893)
Gentiana lutea (FooDB: FOOD00894)
Juniperus communis (FooDB: FOOD00895)
Albizia gummifera (FooDB: FOOD00896)

Fruit

Tropical fruit

Citrus

Lime (FooDB: FOOD00053)
Lemon (FooDB: FOOD00054)
Pummelo (FooDB: FOOD00055)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Sweet orange (FooDB: FOOD00057)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Grapefruit (FooDB: FOOD00256)
Persian lime (FooDB: FOOD00543)
Sour orange (FooDB: FOOD00918)
Mikan (FooDB: FOOD00932)
Clementine (FooDB: FOOD00959)

Pome

Berry

Black crowberry (FooDB: FOOD00075)
Strawberry (FooDB: FOOD00083)
Black huckleberry (FooDB: FOOD00084)
Sea-buckthornberry (FooDB: FOOD00087)
Mulberry (FooDB: FOOD00116)
Black mulberry (FooDB: FOOD00117)
Black chokeberry (FooDB: FOOD00136)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Gooseberry (FooDB: FOOD00157)
Cloudberry (FooDB: FOOD00161)
Red raspberry (FooDB: FOOD00162)
Black raspberry (FooDB: FOOD00163)
Black elderberry (FooDB: FOOD00166)
Rowanberry (FooDB: FOOD00176)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
American cranberry (FooDB: FOOD00192)
Bilberry (FooDB: FOOD00193)
Lingonberry (FooDB: FOOD00194)
Muscadine grape (FooDB: FOOD00203)
Common grape (FooDB: FOOD00204)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Elderberry (FooDB: FOOD00358)
Grape (FooDB: FOOD00369)
Alaska blueberry (FooDB: FOOD00380)
Loganberry (FooDB: FOOD00400)
Ohelo berry (FooDB: FOOD00419)
Salmonberry (FooDB: FOOD00456)
Strawberry guava (FooDB: FOOD00482)
Boysenberry (FooDB: FOOD00542)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)
Rabbiteye blueberry (FooDB: FOOD00898)
Blackberry (FooDB: FOOD00906)
Partridge berry (FooDB: FOOD00931)
Green grape (FooDB: FOOD00964)
Red grape (FooDB: FOOD00965)
Black plum (FooDB: FOOD00966)
Black raisin (FooDB: FOOD00968)
Chinese plum (FooDB: FOOD00978)
Green plum (FooDB: FOOD00979)
Wampee (FooDB: FOOD00980)
Goji (FooDB: FOOD00982)
Monk fruit (FooDB: FOOD00983)
Hawthorn (FooDB: FOOD00985)
Lantern fruit (FooDB: FOOD00986)
Cape gooseberry (FooDB: FOOD00988)

Other fruit

Fig (FooDB: FOOD00081)
Date (FooDB: FOOD00135)
Jujube (FooDB: FOOD00388)

Drupe

Prunus (Cherry, Plum) (FooDB: FOOD00143)
Apricot (FooDB: FOOD00144)
Sweet cherry (FooDB: FOOD00145)
Sour cherry (FooDB: FOOD00146)
European plum (FooDB: FOOD00147)
Peach (FooDB: FOOD00149)
Nectarine (FooDB: FOOD00229)
Peach (var.) (FooDB: FOOD00230)
Common chokecherry (FooDB: FOOD00562)

Nut

Cashew nut (FooDB: FOOD00011)
Peanut (FooDB: FOOD00016)
Brazil nut (FooDB: FOOD00024)
Pecan nut (FooDB: FOOD00044)
Chestnut (FooDB: FOOD00045)
Common hazelnut (FooDB: FOOD00062)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Almond (FooDB: FOOD00148)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hazelnut (FooDB: FOOD00376)
Hickory nut (FooDB: FOOD00377)
Japanese chestnut (FooDB: FOOD00385)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Macadamia nut (FooDB: FOOD00525)
Walnut (FooDB: FOOD00608)

Cereal and cereal product

Cereal

Cereal product

Pasta (FooDB: FOOD00273)
Bulgur (FooDB: FOOD00741)
Semolina (FooDB: FOOD00745)
Flour (FooDB: FOOD00799)

Dough

Sourdough (FooDB: FOOD00275)

Leavened bread

Flat bread

Other bread

Potato bread (FooDB: FOOD00811)

Sweet bread

Raisin bread (FooDB: FOOD00817)

Pulse

Pea

Lentil

Lentils (FooDB: FOOD00098)

Other pulse

Lupine (FooDB: FOOD00104)
White lupine (FooDB: FOOD00403)

Bean

Green lentil (FooDB: FOOD00970)

Gourd

Watermelon (FooDB: FOOD00052)
Muskmelon (FooDB: FOOD00064)
Cucumber (FooDB: FOOD00065)
Cucurbita (FooDB: FOOD00066)
Bitter gourd (FooDB: FOOD00115)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Calabash (FooDB: FOOD00318)
Chayote (FooDB: FOOD00325)
Towel gourd (FooDB: FOOD00492)
Wax gourd (FooDB: FOOD00499)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Acorn squash (FooDB: FOOD00972)
Cantaloupe melon (FooDB: FOOD00984)

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Soy sauce (FooDB: FOOD00694)
Miso (FooDB: FOOD00695)
Tofu (FooDB: FOOD00696)
Soy milk (FooDB: FOOD00736)
Soy cream (FooDB: FOOD00784)

Dish

Other dish

Taco shell (FooDB: FOOD00991)
Tostada shell (FooDB: FOOD00992)

Tea

Herbal tea

Hibiscus tea (FooDB: FOOD00723)
Greenthread tea (FooDB: FOOD00820)

Baking good

Wrapper

Wonton wrapper (FooDB: FOOD00818)

Exogenous (HMDB: HMDB0001052)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0001052)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0001052)
Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)
Valine Degradation (PathBank: SMP0002460)

Disease pathway

2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Isovaleric Acidemia (PathBank: SMP0120589)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
Methylmalonic Aciduria (PathBank: SMP0120525)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Propionic Acidemia (PathBank: SMP0120537)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Isovaleric Aciduria (PathBank: SMP0120723)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Lipid metabolism pathway (HMDB: HMDB0001052)

Cellular process

Cell signaling (HMDB: HMDB0001052)

Biochemical process

Lipid transport (HMDB: HMDB0001052)

Role

Biological role

Energy source (HMDB: HMDB0001052)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0001052)

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	4.14 g/L	ALOGPS
logP	-0.56	ALOGPS
logP	-5.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	183.18 m³·mol⁻¹	ChemAxon
Polarizability	75.7 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
DarkChem	[M+H]+	285.363	31661259
DarkChem	[M-H]-	264.688	31661259
AllCCS	[M+H]+	257.097	32859911
AllCCS	[M-H]-	255.445	32859911
DeepCCS	[M-2H]-	229.64	30932474
DeepCCS	[M+Na]+	204.227	30932474
AllCCS	[M+H]+	257.1	32859911
AllCCS	[M+H-H2O]+	257.5	32859911
AllCCS	[M+NH4]+	256.7	32859911
AllCCS	[M+Na]+	256.5	32859911
AllCCS	[M-H]-	255.4	32859911
AllCCS	[M+Na-2H]-	259.6	32859911
AllCCS	[M+HCOO]-	264.2	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.	3.48 minutes	32390414
Predicted by Siyang on May 30, 2022	10.367 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	9.42 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	548.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1002.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	175.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	87.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	77.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	358.7 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	408.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	910.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	643.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	249.3 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	710.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	264.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	515.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.0 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	564.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-3-Hydroxyisobutyryl-CoA	CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12	5797.0	Standard polar	33892256
(S)-3-Hydroxyisobutyryl-CoA	CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12	4502.0	Standard non polar	33892256
(S)-3-Hydroxyisobutyryl-CoA	CC(CO)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12	6608.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 10V, Positive-QTOF	splash10-000i-1912000120-c718f8aabcd5b3328193	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 20V, Positive-QTOF	splash10-000i-1913000000-86eb8b4e6cdee60b559a	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 40V, Positive-QTOF	splash10-000i-2911000000-2d6f48b3506835c89ffd	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 10V, Negative-QTOF	splash10-00o9-9730140560-056ac34ed9b661751c57	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 20V, Negative-QTOF	splash10-001i-3920110010-37a68eba22e3eecc9757	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 40V, Negative-QTOF	splash10-057i-6900100000-e33bac5e5de19c7b719b	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 10V, Positive-QTOF	splash10-0udi-0000000090-9147721d7b7a39a06164	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 20V, Positive-QTOF	splash10-0fri-1211103790-2282fa97e4f5351f2c0e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 40V, Positive-QTOF	splash10-0002-0129000000-625efeaf22c52212984a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 10V, Negative-QTOF	splash10-0udi-0000000090-ff327f166604b01cb3f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 20V, Negative-QTOF	splash10-0udr-9800102130-8d5a197de5930d76b37c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-3-Hydroxyisobutyryl-CoA 40V, Negative-QTOF	splash10-00p1-9103505710-c610ab0387d6ed968440	2021-09-22	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

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Valine, leucine and isoleucine degradation	Not Available
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		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

FDB022393

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

C06000

BioCyc ID

Not Available

BiGG ID

47176

Wikipedia Link

Not Available

METLIN ID

453

PubChem Compound

PDB ID

Not Available

ChEBI ID

28259

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Hawes, John W.; Harper, Edwin T. Synthesis of methacrylyl-CoA and (R)- and (S)-3-hydroxyisobutyryl-CoA. Methods in Enzymology (2000), 324(Branched-Chain Amino Acids), 73-79.

Material Safety Data Sheet (MSDS)

Not Available

General References

Loupatty FJ, Clayton PT, Ruiter JP, Ofman R, Ijlst L, Brown GK, Thorburn DR, Harris RA, Duran M, Desousa C, Krywawych S, Heales SJ, Wanders RJ: Mutations in the gene encoding 3-hydroxyisobutyryl-CoA hydrolase results in progressive infantile neurodegeneration. Am J Hum Genet. 2007 Jan;80(1):195-9. Epub 2006 Nov 30. [PubMed:17160907 ]
Lehnert W, Sass JO: Glutaconyl-CoA is the main toxic agent in glutaryl-CoA dehydrogenase deficiency (glutaric aciduria type I). Med Hypotheses. 2005;65(2):330-3. [PubMed:15922108 ]

Enzymes

Enzyme Details

1. Peroxisomal bifunctional enzyme

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: EHHADH
Uniprot ID:: Q08426
Molecular weight:: 69153.26

Reactions

Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA	details

Enzyme Details

2. Enoyl-CoA hydratase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:: ECHS1
Uniprot ID:: P30084
Molecular weight:: 31387.085

Reactions

Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA	details

Enzyme Details

3. Trifunctional enzyme subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Bifunctional subunit.
Gene Name:: HADHA
Uniprot ID:: P40939
Molecular weight:: 82998.97

Reactions

Methacrylyl-CoA + Water → (S)-3-Hydroxyisobutyryl-CoA	details

Enzyme Details

4. 3-hydroxyisobutyryl-CoA hydrolase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes 3-hydroxyisobutyryl-CoA (HIBYL-CoA), a saline catabolite. Has high activity toward isobutyryl-CoA. Could be an isobutyryl-CoA dehydrogenase that functions in valine catabolism. Also hydrolyzes 3-hydroxypropanoyl-CoA.
Gene Name:: HIBCH
Uniprot ID:: Q6NVY1
Molecular weight:: 43481.935

Reactions

(S)-3-Hydroxyisobutyryl-CoA + Water → Coenzyme A + (S)-3-Hydroxyisobutyric acid	details
(S)-3-Hydroxyisobutyryl-CoA + Water → Coenzyme A + (S)-3-Hydroxyisobutyric acid	details

Showing metabocard for (S)-3-Hydroxyisobutyryl-CoA (HMDB0001052)

MOL for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

3D MOL for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

3D SDF for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

3D-SDF for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

PDB for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

3D PDB for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

SMILES for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

INCHI for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

Structure for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

3D Structure for HMDB0001052 ((S)-3-Hydroxyisobutyryl-CoA)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

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