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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-10-30 10:32:48 UTC

Update Date

2022-03-07 03:17:34 UTC

HMDB ID

HMDB0059635

Secondary Accession Numbers

HMDB59635

Metabolite Identification

Common Name

Lipoyl-AMP

Description

Lipoyl-AMP belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated. Lipoyl-AMP is a strong basic compound (based on its pKa).

Structure

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

 
  Mrv0541 02241222112D          
 
 34 37  0  0  1  0            999 V2000
   11.8197  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9932  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064  -11.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0677  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7702  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5141  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2167  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9193  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -12.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4904  -10.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1103  -10.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7051  -10.7039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7797   -9.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8542  -10.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1929  -11.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0439  -10.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4572  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6062   -9.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5981  -10.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9782  -12.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3827  -10.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6306  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6807  -11.5304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2180  -10.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5974  -10.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.9518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -11.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2660  -12.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8165  -12.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 16 20  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 29 32  1  0  0  0  0
 10 32  1  0  0  0  0
 24 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

 
  Mrv0541 02241222112D          
 
 34 37  0  0  1  0            999 V2000
   11.8197  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.9932  -10.1666    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7452  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4064  -11.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0677  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7702  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5141  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2167  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9193  -10.9518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -11.3651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6632  -12.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4904  -10.4559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1103  -10.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7051  -10.7039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.7797   -9.6293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8542  -10.3319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1929  -11.7370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0439  -10.1666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4572  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6062   -9.6293    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5981  -10.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9782  -12.0677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3827  -10.6625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.6306  -11.4478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.6807  -11.5304    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.2180  -10.1666    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5974  -10.4146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9775  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.9518    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -11.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1510  -10.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3244  -10.9518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2660  -12.1558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8165  -12.1596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 13 17  1  0  0  0  0
 14 18  1  0  0  0  0
 14 19  1  0  0  0  0
 15 20  2  0  0  0  0
 16 21  1  0  0  0  0
 17 22  2  0  0  0  0
 18 23  1  0  0  0  0
 19 24  1  0  0  0  0
 21 25  2  0  0  0  0
 21 26  1  0  0  0  0
 23 27  1  1  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 16 20  1  0  0  0  0
 22 25  1  0  0  0  0
 23 24  1  0  0  0  0
 29 32  1  0  0  0  0
 10 32  1  0  0  0  0
 24 33  1  6  0  0  0
 19 34  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0059635

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1

> <INCHI_KEY>
QWEGOCJRZOKSOE-NLJBGGCZSA-N

> <FORMULA>
C18H26N5O8PS2

> <MOLECULAR_WEIGHT>
535.532

> <EXACT_MASS>
535.096040725

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_AVERAGE_POLARIZABILITY>
50.70841164834475

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid

> <ALOGPS_LOGP>
0.25

> <JCHEM_LOGP>
-2.322057993323983

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.457192389903962

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8302712598949102

> <JCHEM_PKA_STRONGEST_BASIC>
4.988470657284801

> <JCHEM_POLAR_SURFACE_AREA>
192.13999999999996

> <JCHEM_REFRACTIVITY>
124.9477

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
Lipoyl-AMP

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0      22.063 -18.978   0.000  0.00  0.00           S+0
HETATM    2  S   UNK     0      20.521 -18.978   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      20.058 -20.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.292 -21.369   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.526 -20.443   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.838 -21.215   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.226 -20.443   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.538 -21.215   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.849 -20.443   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.238 -21.215   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      29.238 -22.758   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      40.115 -19.518   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0      41.273 -20.289   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      38.650 -19.981   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.655 -17.975   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.661 -19.286   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      41.427 -21.909   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      37.415 -18.978   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      38.187 -21.369   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      42.198 -17.975   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      44.050 -19.903   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.893 -22.526   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      36.181 -19.903   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      36.644 -21.369   0.000  0.00  0.00           C+0
HETATM   25  N   UNK     0      44.204 -21.523   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      45.207 -18.978   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      34.715 -19.441   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      33.558 -20.443   0.000  0.00  0.00           O+0
HETATM   29  P   UNK     0      32.015 -20.443   0.000  0.00  0.00           P+0
HETATM   30  O   UNK     0      32.015 -21.986   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      32.015 -18.901   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      30.472 -20.443   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      35.963 -22.691   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      38.857 -22.698   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    1    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   32                                                  
CONECT   11   10                                                            
CONECT   12   13   14   15                                                  
CONECT   13   12   16   17                                                  
CONECT   14   12   18   19                                                  
CONECT   15   12   20                                                       
CONECT   16   13   21   20                                                  
CONECT   17   13   22                                                       
CONECT   18   14   23                                                       
CONECT   19   14   24   34                                                  
CONECT   20   15   16                                                       
CONECT   21   16   25   26                                                  
CONECT   22   17   25                                                       
CONECT   23   18   27   24                                                  
CONECT   24   19   23   33                                                  
CONECT   25   21   22                                                       
CONECT   26   21                                                            
CONECT   27   23   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   10                                                       
CONECT   33   24                                                            
CONECT   34   19                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

COMPND    HMDB0059635
HETATM    1  N1  UNL     1     -10.234  -0.332  -0.921  1.00  0.00           N  
HETATM    2  C1  UNL     1      -8.829  -0.534  -0.998  1.00  0.00           C  
HETATM    3  N2  UNL     1      -8.314  -1.383  -1.905  1.00  0.00           N  
HETATM    4  C2  UNL     1      -6.982  -1.589  -1.995  1.00  0.00           C  
HETATM    5  N3  UNL     1      -6.137  -0.944  -1.171  1.00  0.00           N  
HETATM    6  C3  UNL     1      -6.576  -0.095  -0.255  1.00  0.00           C  
HETATM    7  C4  UNL     1      -7.945   0.117  -0.164  1.00  0.00           C  
HETATM    8  N4  UNL     1      -8.113   1.001   0.822  1.00  0.00           N  
HETATM    9  C5  UNL     1      -6.893   1.325   1.322  1.00  0.00           C  
HETATM   10  N5  UNL     1      -5.936   0.649   0.659  1.00  0.00           N  
HETATM   11  C6  UNL     1      -4.532   0.740   0.914  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.749   0.583  -0.230  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.464   0.453   0.231  1.00  0.00           C  
HETATM   14  C8  UNL     1      -1.594  -0.325  -0.759  1.00  0.00           C  
HETATM   15  O2  UNL     1      -0.303  -0.460  -0.305  1.00  0.00           O  
HETATM   16  P1  UNL     1       0.596  -1.313  -1.422  1.00  0.00           P  
HETATM   17  O3  UNL     1       0.140  -2.736  -1.438  1.00  0.00           O  
HETATM   18  O4  UNL     1       0.367  -0.704  -3.005  1.00  0.00           O  
HETATM   19  O5  UNL     1       2.290  -1.195  -1.116  1.00  0.00           O  
HETATM   20  C9  UNL     1       2.951   0.018  -1.128  1.00  0.00           C  
HETATM   21  O6  UNL     1       2.274   1.045  -1.371  1.00  0.00           O  
HETATM   22  C10 UNL     1       4.430   0.149  -0.864  1.00  0.00           C  
HETATM   23  C11 UNL     1       4.873   1.560  -0.938  1.00  0.00           C  
HETATM   24  C12 UNL     1       6.328   1.722  -0.731  1.00  0.00           C  
HETATM   25  C13 UNL     1       6.988   1.376   0.520  1.00  0.00           C  
HETATM   26  C14 UNL     1       6.999   0.022   1.082  1.00  0.00           C  
HETATM   27  C15 UNL     1       7.591  -1.039   0.216  1.00  0.00           C  
HETATM   28  C16 UNL     1       8.892  -0.583  -0.351  1.00  0.00           C  
HETATM   29  S1  UNL     1       9.928  -0.397   1.163  1.00  0.00           S  
HETATM   30  S2  UNL     1       8.283   0.022   2.470  1.00  0.00           S  
HETATM   31  C17 UNL     1      -2.506  -0.222   1.572  1.00  0.00           C  
HETATM   32  O7  UNL     1      -2.126   0.671   2.601  1.00  0.00           O  
HETATM   33  C18 UNL     1      -4.015  -0.420   1.768  1.00  0.00           C  
HETATM   34  O8  UNL     1      -4.391  -0.285   3.082  1.00  0.00           O  
HETATM   35  H1  UNL     1     -10.881  -1.123  -0.703  1.00  0.00           H  
HETATM   36  H2  UNL     1     -10.674   0.605  -1.077  1.00  0.00           H  
HETATM   37  H3  UNL     1      -6.615  -2.294  -2.755  1.00  0.00           H  
HETATM   38  H4  UNL     1      -6.742   2.027   2.136  1.00  0.00           H  
HETATM   39  H5  UNL     1      -4.215   1.663   1.399  1.00  0.00           H  
HETATM   40  H6  UNL     1      -2.030   1.465   0.350  1.00  0.00           H  
HETATM   41  H7  UNL     1      -1.671   0.164  -1.743  1.00  0.00           H  
HETATM   42  H8  UNL     1      -2.065  -1.346  -0.815  1.00  0.00           H  
HETATM   43  H9  UNL     1       0.523  -1.435  -3.657  1.00  0.00           H  
HETATM   44  H10 UNL     1       4.571  -0.253   0.130  1.00  0.00           H  
HETATM   45  H11 UNL     1       5.007  -0.431  -1.616  1.00  0.00           H  
HETATM   46  H12 UNL     1       4.634   2.020  -1.946  1.00  0.00           H  
HETATM   47  H13 UNL     1       4.285   2.226  -0.229  1.00  0.00           H  
HETATM   48  H14 UNL     1       6.530   2.852  -0.884  1.00  0.00           H  
HETATM   49  H15 UNL     1       6.867   1.308  -1.645  1.00  0.00           H  
HETATM   50  H16 UNL     1       8.086   1.719   0.501  1.00  0.00           H  
HETATM   51  H17 UNL     1       6.593   2.056   1.363  1.00  0.00           H  
HETATM   52  H18 UNL     1       6.134  -0.357   1.608  1.00  0.00           H  
HETATM   53  H19 UNL     1       6.894  -1.451  -0.542  1.00  0.00           H  
HETATM   54  H20 UNL     1       7.821  -1.915   0.892  1.00  0.00           H  
HETATM   55  H21 UNL     1       8.908   0.394  -0.825  1.00  0.00           H  
HETATM   56  H22 UNL     1       9.293  -1.401  -0.966  1.00  0.00           H  
HETATM   57  H23 UNL     1      -1.956  -1.166   1.619  1.00  0.00           H  
HETATM   58  H24 UNL     1      -1.389   0.257   3.091  1.00  0.00           H  
HETATM   59  H25 UNL     1      -4.256  -1.400   1.318  1.00  0.00           H  
HETATM   60  H26 UNL     1      -4.944  -1.081   3.323  1.00  0.00           H  
CONECT    1    2   35   36
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   37
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   38
CONECT   10   11
CONECT   11   12   33   39
CONECT   12   13
CONECT   13   14   31   40
CONECT   14   15   41   42
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   43
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   44   45
CONECT   23   24   46   47
CONECT   24   25   48   49
CONECT   25   26   50   51
CONECT   26   27   30   52
CONECT   27   28   53   54
CONECT   28   29   55   56
CONECT   29   30
CONECT   31   32   33   57
CONECT   32   58
CONECT   33   34   59
CONECT   34   60
END

HMDB0059635
     RDKit          3D
Lipoyl-AMP
 60 63  0  0  0  0  0  0  0  0999 V2000
  -10.2338   -0.3316   -0.9209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8289   -0.5342   -0.9982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3140   -1.3829   -1.9054 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9825   -1.5890   -1.9947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1373   -0.9440   -1.1709 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5761   -0.0949   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9449    0.1166   -0.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1131    1.0009    0.8218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8925    1.3247    1.3220 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9363    0.6495    0.6594 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5316    0.7401    0.9144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7486    0.5831   -0.2299 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4639    0.4532    0.2308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5940   -0.3249   -0.7595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3029   -0.4601   -0.3053 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5963   -1.3135   -1.4221 P   0  0  0  0  0  5  0  0  0  0  0  0
    0.1403   -2.7361   -1.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3670   -0.7036   -3.0047 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2903   -1.1954   -1.1162 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9509    0.0179   -1.1279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2738    1.0453   -1.3705 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4302    0.1490   -0.8640 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8729    1.5598   -0.9383 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3282    1.7221   -0.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9875    1.3757    0.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9987    0.0224    1.0818 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5913   -1.0390    0.2157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8919   -0.5834   -0.3505 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9281   -0.3974    1.1630 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2834    0.0224    2.4699 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5055   -0.2221    1.5718 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1259    0.6705    2.6015 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0154   -0.4201    1.7680 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3907   -0.2851    3.0815 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8815   -1.1232   -0.7027 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6741    0.6052   -1.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6153   -2.2941   -2.7549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7419    2.0274    2.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2152    1.6631    1.3988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296    1.4652    0.3503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6708    0.1642   -1.7429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0655   -1.3461   -0.8152 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5225   -1.4350   -3.6569 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5715   -0.2530    0.1297 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0070   -0.4314   -1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6336    2.0202   -1.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2850    2.2264   -0.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5303    2.8519   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8672    1.3079   -1.6451 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0857    1.7188    0.5005 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5932    2.0558    1.3629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1344   -0.3566    1.6078 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8944   -1.4506   -0.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8211   -1.9153    0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9078    0.3944   -0.8246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2931   -1.4011   -0.9659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560   -1.1655    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3892    0.2567    3.0907 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2563   -1.4000    1.3180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9444   -1.0811    3.3226 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 13 31  1  0
 31 32  1  0
 31 33  1  0
 33 34  1  0
  7  2  1  0
 33 11  1  0
 10  6  1  0
 30 26  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  9 38  1  0
 11 39  1  1
 13 40  1  1
 14 41  1  0
 14 42  1  0
 18 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 28 55  1  0
 28 56  1  0
 31 57  1  6
 32 58  1  0
 33 59  1  6
 34 60  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₆N₅O₈PS₂

Average Molecular Weight

535.532

Monoisotopic Molecular Weight

535.096040725

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[5-(1,2-dithiolan-3-yl)pentanoyl]oxy})phosphinic acid

Traditional Name

Lipoyl-AMP

CAS Registry Number

Not Available

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C18H26N5O8PS2/c19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)11(30-18)7-29-32(27,28)31-12(24)4-2-1-3-10-5-6-33-34-10/h8-11,14-15,18,25-26H,1-7H2,(H,27,28)(H2,19,20,21)/t10?,11-,14-,15-,18-/m1/s1

InChI Key

QWEGOCJRZOKSOE-NLJBGGCZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 5'-acylphosphoadenosines. These are ribonucleoside derivatives containing an adenoside moiety, where the phosphate group is acylated.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Purine nucleotides

Sub Class

Purine ribonucleotides

Direct Parent

5'-acylphosphoadenosines

Alternative Parents

Substituents

5'-acylphosphoadenosine
Pentose-5-phosphate
Pentose phosphate
Lipoic_acid_derivative
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
6-aminopurine
Pentose monosaccharide
Imidazopyrimidine
Purine
Aminopyrimidine
Monoalkyl phosphate
Acyl phosphate
Monosaccharide
Imidolactam
N-substituted imidazole
Alkyl phosphate
Organic phosphoric acid derivative
Pyrimidine
Phosphoric acid ester
Azole
Dithiolane
Imidazole
Heteroaromatic compound
1,2-dithiolane
Tetrahydrofuran
Organic disulfide
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid salt
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Primary amine
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Amine
Organonitrogen compound
Organooxygen compound
Alcohol
Organic salt
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dithiolanes (CHEBI:55451 )
purine ribonucleoside 5'-monophosphate (CHEBI:55451 )
acyclic mixed acid anhydride (CHEBI:55451 )

Ontology

Not Available

Exogenous (HMDB: HMDB0059635)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Lipoic Acid Metabolism (PathBank: SMP0002398)

Role

Not Available

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	1.12 g/L	ALOGPS
logP	0.25	ALOGPS
logP	-2.3	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	192.14 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	124.95 m³·mol⁻¹	ChemAxon
Polarizability	50.71 Å³	ChemAxon
Number of Rings	4	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]+	220.95	31661259
DarkChem	[M-H]-	205.779	31661259
DeepCCS	[M+H]+	192.622	30932474
DeepCCS	[M-H]-	190.227	30932474
DeepCCS	[M-2H]-	223.562	30932474
DeepCCS	[M+Na]+	198.535	30932474
AllCCS	[M+H]+	214.3	32859911
AllCCS	[M+H-H2O]+	212.9	32859911
AllCCS	[M+NH4]+	215.6	32859911
AllCCS	[M+Na]+	216.0	32859911
AllCCS	[M-H]-	202.2	32859911
AllCCS	[M+Na-2H]-	203.4	32859911
AllCCS	[M+HCOO]-	204.9	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.	3.61 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4914 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.82 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1667.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	181.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	153.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	84.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	354.7 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	351.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	613.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	691.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	365.0 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	755.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	211.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	482.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.2 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	358.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Lipoyl-AMP	NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O	5211.5	Standard polar	33892256
Lipoyl-AMP	NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O	3468.7	Standard non polar	33892256
Lipoyl-AMP	NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O	4586.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Lipoyl-AMP,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	4579.9	Semi standard non polar	33892256
Lipoyl-AMP,1TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N)N=CN=C21	4573.7	Semi standard non polar	33892256
Lipoyl-AMP,1TMS,isomer #3	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4569.6	Semi standard non polar	33892256
Lipoyl-AMP,1TMS,isomer #4	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O	4591.9	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	4479.9	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	4497.5	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C)[C@H]1O	4525.1	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@H]1N1C=NC2=C(N)N=CN=C21	4491.3	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O[Si](C)(C)C	4529.4	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #6	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O)[C@H]1O	4532.7	Semi standard non polar	33892256
Lipoyl-AMP,2TMS,isomer #7	C[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O)[Si](C)(C)C	4475.8	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	4415.6	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C	3978.5	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4470.0	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #2	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4115.8	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	4489.0	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #3	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O	4185.0	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	4399.7	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	4162.4	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	4490.9	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #5	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C	4187.3	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	4396.4	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	4163.1	Standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #7	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4421.0	Semi standard non polar	33892256
Lipoyl-AMP,3TMS,isomer #7	C[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4224.2	Standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4448.2	Semi standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #1	C[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4088.7	Standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	4369.1	Semi standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #2	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	4068.6	Standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	4394.9	Semi standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O	4126.2	Standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	4391.6	Semi standard non polar	33892256
Lipoyl-AMP,4TMS,isomer #4	C[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@H]1N1C=NC2=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C21	4127.4	Standard non polar	33892256
Lipoyl-AMP,5TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	4394.1	Semi standard non polar	33892256
Lipoyl-AMP,5TMS,isomer #1	C[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C)O[C@@H](N2C=NC3=C(N([Si](C)(C)C)[Si](C)(C)C)N=CN=C32)[C@@H]1O[Si](C)(C)C	4010.0	Standard non polar	33892256
Lipoyl-AMP,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	4770.9	Semi standard non polar	33892256
Lipoyl-AMP,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N)N=CN=C21	4770.6	Semi standard non polar	33892256
Lipoyl-AMP,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4764.2	Semi standard non polar	33892256
Lipoyl-AMP,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O	4781.2	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	4821.6	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O	4840.6	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4841.3	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=NC2=C(N)N=CN=C21	4830.0	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4840.7	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O	4844.2	Semi standard non polar	33892256
Lipoyl-AMP,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)N(C1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O)[C@H]1O)[Si](C)(C)C(C)(C)C	4822.2	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	4884.3	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=NC3=C(N)N=CN=C32)[C@@H]1O[Si](C)(C)C(C)(C)C	4452.0	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4883.0	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4645.8	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4911.1	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	4662.7	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O	4871.3	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@@H]1O	4689.5	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4904.0	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(=O)(OC(=O)CCCCC2CCSS2)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	4664.2	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	4863.8	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OC(=O)CCCCC2CCSS2)O[C@H]1N1C=NC2=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C21	4693.3	Standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4870.7	Semi standard non polar	33892256
Lipoyl-AMP,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=NC3=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=CN=C32)[C@H](O)[C@@H]1O)OC(=O)CCCCC1CCSS1	4709.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (Non-derivatized) - 70eV, Positive	splash10-02ds-3913010000-e06df70a38935bfec6ca	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (2 TMS) - 70eV, Positive	splash10-03xs-9852448000-ab8656a944a15acff0d2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_6) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS (TBDMS_2_7) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Lipoyl-AMP GC-MS ("Lipoyl-AMP,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 10V, Positive-QTOF	splash10-000i-0911020000-403226dda50e9b19c782	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 20V, Positive-QTOF	splash10-000i-1900000000-09f2e5c022805e4e9fe4	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 40V, Positive-QTOF	splash10-000i-1900000000-8cffaab609f0ad97292d	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 10V, Negative-QTOF	splash10-003r-3779560000-3583b9a6776d5e619ce6	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 20V, Negative-QTOF	splash10-003r-5911000000-bd5c472188d51d73ad0c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 40V, Negative-QTOF	splash10-003r-9500000000-b3956188225c40fb0715	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 10V, Negative-QTOF	splash10-001i-0000090000-97f9a62a74dc17a227c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 20V, Negative-QTOF	splash10-0059-9100360000-0957a91a14ca65d00ed6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 40V, Negative-QTOF	splash10-01u0-9200000000-598cbfd3e15d0060e791	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 10V, Positive-QTOF	splash10-000i-0101090000-158a5093458bb19523bb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 20V, Positive-QTOF	splash10-000i-0900000000-55f0391000d477c8c77d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lipoyl-AMP 40V, Positive-QTOF	splash10-000i-0920000000-c5661a88a8e2cb7260af	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

26330628

KEGG Compound ID

C16238

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23724672

PDB ID

Not Available

ChEBI ID

55451

Food Biomarker Ontology

Not Available

VMH ID

CE5656

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Lipoyltransferase 1, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Catalyzes the transfer of the lipoyl group from lipoyl-AMP to the specific lysine residue of lipoyl domains of lipoate-dependent enzymes (By similarity).
Gene Name:: LIPT1
Uniprot ID:: Q9Y234
Molecular weight:: 42478.8

Reactions

Lipoyl-AMP + protein → protein N(6)-(lipoyl)lysine + Adenosine monophosphate	details

Showing metabocard for Lipoyl-AMP (HMDB0059635)

MOL for HMDB0059635 (Lipoyl-AMP)

3D MOL for HMDB0059635 (Lipoyl-AMP)

3D SDF for HMDB0059635 (Lipoyl-AMP)

3D-SDF for HMDB0059635 (Lipoyl-AMP)

PDB for HMDB0059635 (Lipoyl-AMP)

3D PDB for HMDB0059635 (Lipoyl-AMP)

SMILES for HMDB0059635 (Lipoyl-AMP)

INCHI for HMDB0059635 (Lipoyl-AMP)

Structure for HMDB0059635 (Lipoyl-AMP)

3D Structure for HMDB0059635 (Lipoyl-AMP)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions