MiMeDB: Showing metabocard for Biotinyl-5'-AMP (MMDBc0029821)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:06 UTC

Update Date

2024-04-30 19:42:24 UTC

Metabolite ID

MMDBc0029821

Metabolite Identification

Common Name

Biotinyl-5'-AMP

Description

5'-biotinyl-AMP (B-AMP) is the active form of biotin. Biotin is essential to maintain metabolic homeostasis and as regulator of gene expression. The vitamin biotin plays an essential role in gluconeogenesis, fatty acid synthesis, and carbohydrate metabolism because of its role as cofactor of five carboxylases; pyruvate carboxylase (PC), propionyl-CoA carboxylase (PCC), methylcrotonyl-CoA carboxylase, and two forms of acetyl-CoA carboxylase (ACC-1 and ACC-2). Carboxylase biotinylation is catalyzed by the enzyme holocarboxylase synthetase (HCS) through a reaction that involves the transformation of biotin into B-AMP and its subsequent attachment to a specific lysine residue in the carboxylases. B-AMP is also required to activate a signal transduction cascade that includes a soluble guanylate cyclase (sGC) and cGMP-dependent protein kinase (PKG). The regulatory role of biotin in the biotin cycle seems to be limited to the expression of proteins involved in the transport and utilization of exogenous vitamin while having no effect on biotinidase mRNA levels, enzyme responsible for biotin recycling during carboxylase turnover.

Structure

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


  Mrv0541 02231219542D          

 38 42  0  0  1  0            999 V2000
   28.1421  -16.6658    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0926  -20.9871    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.9204  -23.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8589  -22.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8558  -24.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7854  -16.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3462  -21.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8390  -20.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3075  -21.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4792  -20.6413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8777  -20.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0930  -17.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0976  -15.9913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1479  -24.8492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1479  -26.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -24.6881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9383  -25.9256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -27.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8785  -17.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8814  -16.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6583  -17.3281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.6628  -16.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9118  -18.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6104  -16.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7185  -18.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1906  -22.9865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.1892  -23.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.4064  -22.7302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.4041  -24.0651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.9721  -19.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1529  -21.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7788  -19.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3672  -25.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6294  -25.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3672  -25.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0323  -20.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -26.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9383  -25.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 21  1  0  0  0  0
  1 22  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 11  2  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6 24  2  0  0  0  0
  7 31  1  0  0  0  0
  8 36  1  0  0  0  0
 10 36  2  0  0  0  0
 12 19  1  0  0  0  0
 12 24  1  0  0  0  0
 13 20  1  0  0  0  0
 13 24  1  0  0  0  0
 29 14  1  6  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 15 34  2  0  0  0  0
 15 35  1  0  0  0  0
 16 33  1  0  0  0  0
 16 38  2  0  0  0  0
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 17 38  1  0  0  0  0
 18 37  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 25  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 36  1  0  0  0  0
 33 35  2  0  0  0  0
 35 37  1  0  0  0  0
M  END

HMDB0004220
     RDKit          3D
Biotinyl-5'-AMP
 66 70  0  0  0  0  0  0  0  0999 V2000
   -9.5314    1.6288    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3567    0.8931    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8460    0.7821    2.6394 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.0819    2.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0846   -0.5152    1.8539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5253   -0.4552    0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6931    0.2694    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9099    0.1657   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9176   -0.5820   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0709   -0.9614   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848   -1.7664   -0.7295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0689   -1.6916    0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.7314    0.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -0.4303    0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.2088    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393    1.2462    2.1537 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2653    1.3044    3.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.5379    1.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    1.3447    1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.6682    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643    1.9221   -0.5599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    1.7282   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075    0.3354   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.2063   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735    1.1024    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3350    1.1181    0.2044 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8084    1.6168   -1.4862 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9801    0.2395   -1.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.7680   -0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7020   -1.5326   -0.4091 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2543   -0.8360    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4137   -0.9342    1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2881    0.0605    1.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0915   -0.1254    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6802   -1.7469   -1.4997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650   -3.0652   -1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542   -1.2188   -1.8541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4670   -1.7011   -3.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4132    1.1241    0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5980    2.6637    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3692    0.0403    3.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -0.7987   -2.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384   -2.8192   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -2.5761    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.5816    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803    0.3560   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    3.2773    1.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    2.0801   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    2.4560    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -0.3230   -0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    0.0039    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357   -0.8560   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    0.3766   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5338    2.1793    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982    0.8035    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    1.9286    0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9948    0.6249   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562   -0.1561   -2.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619   -1.4436   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898   -2.4012   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3538    0.7235    2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192   -0.8383    0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.1059   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242   -3.6809   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -0.1266   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7469   -0.9115   -3.6335 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
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 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 13 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
  7  2  1  0
 37 11  1  0
 10  6  1  0
 34 26  1  0
 34 29  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  9 42  1  0
 11 43  1  6
 13 44  1  1
 14 45  1  0
 14 46  1  0
 18 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
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 25 54  1  0
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 26 56  1  1
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 28 58  1  0
 29 59  1  0
 30 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  1
 36 64  1  0
 37 65  1  6
 38 66  1  0
M  END


  Mrv0541 02231219542D          

 38 42  0  0  1  0            999 V2000
   28.1421  -16.6658    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.0926  -20.9871    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.9204  -23.3967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8589  -22.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8558  -24.2976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7854  -16.6542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3462  -21.7722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8390  -20.2021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3075  -21.2407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4792  -20.6413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8777  -20.7335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0930  -17.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.0976  -15.9913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1479  -24.8492    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.1479  -26.1771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -24.6881    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.9383  -25.9256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -27.1631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8785  -17.0740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8814  -16.2490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6583  -17.3281    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.6628  -16.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9118  -18.1131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6104  -16.6571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7185  -18.2861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1906  -22.9865    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   33.1892  -23.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   32.4064  -22.7302    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   32.4041  -24.0651    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.9721  -19.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1529  -21.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7788  -19.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3672  -25.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6294  -25.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.3672  -25.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0323  -20.0291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6527  -26.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9383  -25.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1 22  1  0  0  0  0
  2  7  1  0  0  0  0
  2  8  1  0  0  0  0
  2  9  1  0  0  0  0
  2 11  2  0  0  0  0
  3 28  1  0  0  0  0
  3 29  1  0  0  0  0
 26  4  1  1  0  0  0
 27  5  1  1  0  0  0
  6 24  2  0  0  0  0
  7 31  1  0  0  0  0
  8 36  1  0  0  0  0
 10 36  2  0  0  0  0
 12 19  1  0  0  0  0
 12 24  1  0  0  0  0
 13 20  1  0  0  0  0
 13 24  1  0  0  0  0
 29 14  1  6  0  0  0
 14 33  1  0  0  0  0
 14 34  1  0  0  0  0
 15 34  2  0  0  0  0
 15 35  1  0  0  0  0
 16 33  1  0  0  0  0
 16 38  2  0  0  0  0
 17 37  2  0  0  0  0
 17 38  1  0  0  0  0
 18 37  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 23  1  1  0  0  0
 23 25  1  0  0  0  0
 25 30  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 27 29  1  0  0  0  0
 28 31  1  6  0  0  0
 30 32  1  0  0  0  0
 32 36  1  0  0  0  0
 33 35  2  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029821

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28N7O9PS/c21-17-14-18(23-7-22-17)27(8-24-14)19-16(30)15(29)10(35-19)5-34-37(32,33)36-12(28)4-2-1-3-11-13-9(6-38-11)25-20(31)26-13/h7-11,13,15-16,19,29-30H,1-6H2,(H,32,33)(H2,21,22,23)(H2,25,26,31)/t9?,10-,11+,13?,15-,16-,19-/m1/s1

> <INCHI_KEY>
UTQCSTJVMLODHM-CFYKWCKVSA-N

> <FORMULA>
C20H28N7O9PS

> <MOLECULAR_WEIGHT>
573.517

> <EXACT_MASS>
573.140682731

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
53.923433269903185

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <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-[(4S)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid

> <ALOGPS_LOGP>
-1.24

> <JCHEM_LOGP>
-4.116413751955203

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.413157781220377

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8302692044640101

> <JCHEM_PKA_STRONGEST_BASIC>
4.988470655480461

> <JCHEM_POLAR_SURFACE_AREA>
233.27

> <JCHEM_REFRACTIVITY>
130.62719999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({5-[(4S)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0004220
     RDKit          3D
Biotinyl-5'-AMP
 66 70  0  0  0  0  0  0  0  0999 V2000
   -9.5314    1.6288    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3567    0.8931    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8460    0.7821    2.6394 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.0819    2.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0846   -0.5152    1.8539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5253   -0.4552    0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6931    0.2694    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9099    0.1657   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9176   -0.5820   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0709   -0.9614   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848   -1.7664   -0.7295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0689   -1.6916    0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.7314    0.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -0.4303    0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.2088    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393    1.2462    2.1537 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2653    1.3044    3.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.5379    1.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    1.3447    1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.6682    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643    1.9221   -0.5599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    1.7282   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075    0.3354   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.2063   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735    1.1024    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3350    1.1181    0.2044 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8084    1.6168   -1.4862 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9801    0.2395   -1.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.7680   -0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7020   -1.5326   -0.4091 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2543   -0.8360    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4137   -0.9342    1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2881    0.0605    1.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0915   -0.1254    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6802   -1.7469   -1.4997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650   -3.0652   -1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542   -1.2188   -1.8541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4670   -1.7011   -3.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4132    1.1241    0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5980    2.6637    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3692    0.0403    3.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -0.7987   -2.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384   -2.8192   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -2.5761    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.5816    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803    0.3560   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    3.2773    1.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    2.0801   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    2.4560    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -0.3230   -0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    0.0039    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357   -0.8560   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    0.3766   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5338    2.1793    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982    0.8035    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    1.9286    0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9948    0.6249   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562   -0.1561   -2.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619   -1.4436   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898   -2.4012   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3538    0.7235    2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192   -0.8383    0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.1059   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242   -3.6809   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -0.1266   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7469   -0.9115   -3.6335 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
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 13 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
  7  2  1  0
 37 11  1  0
 10  6  1  0
 34 26  1  0
 34 29  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  9 42  1  0
 11 43  1  6
 13 44  1  1
 14 45  1  0
 14 46  1  0
 18 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 28 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  1
 36 64  1  0
 37 65  1  6
 38 66  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      52.532 -31.109   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      58.040 -39.176   0.000  0.00  0.00           P+0
HETATM    3  O   UNK     0      59.585 -43.674   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      63.203 -42.005   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      63.197 -45.356   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      46.266 -31.088   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      58.513 -40.641   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      57.566 -37.711   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      56.574 -39.649   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      55.028 -38.530   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      59.505 -38.703   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0      48.707 -32.342   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      48.716 -29.850   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0      60.009 -46.385   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      60.009 -48.864   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      57.218 -46.084   0.000  0.00  0.00           N+0
HETATM   17  N   UNK     0      55.885 -48.394   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      57.218 -50.704   0.000  0.00  0.00           N+0
HETATM   19  C   UNK     0      50.173 -31.871   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      50.179 -30.331   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      51.629 -32.346   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      51.637 -29.867   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      52.102 -33.811   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      47.806 -31.093   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      53.608 -34.134   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      61.956 -42.908   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      61.953 -44.448   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      60.492 -42.430   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      60.488 -44.922   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      54.081 -35.599   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      60.019 -40.964   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      55.587 -35.922   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      58.552 -46.854   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      60.908 -47.624   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      58.552 -48.394   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      56.060 -37.388   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      57.218 -49.164   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      55.885 -46.854   0.000  0.00  0.00           C+0
CONECT    1   21   22                                                       
CONECT    2    7    8    9   11                                             
CONECT    3   28   29                                                       
CONECT    4   26                                                            
CONECT    5   27                                                            
CONECT    6   24                                                            
CONECT    7    2   31                                                       
CONECT    8    2   36                                                       
CONECT    9    2                                                            
CONECT   10   36                                                            
CONECT   11    2                                                            
CONECT   12   19   24                                                       
CONECT   13   20   24                                                       
CONECT   14   29   33   34                                                  
CONECT   15   34   35                                                       
CONECT   16   33   38                                                       
CONECT   17   37   38                                                       
CONECT   18   37                                                            
CONECT   19   12   20   21                                                  
CONECT   20   13   19   22                                                  
CONECT   21    1   19   23                                                  
CONECT   22    1   20                                                       
CONECT   23   21   25                                                       
CONECT   24    6   12   13                                                  
CONECT   25   23   30                                                       
CONECT   26    4   27   28                                                  
CONECT   27    5   26   29                                                  
CONECT   28    3   26   31                                                  
CONECT   29    3   14   27                                                  
CONECT   30   25   32                                                       
CONECT   31    7   28                                                       
CONECT   32   30   36                                                       
CONECT   33   14   16   35                                                  
CONECT   34   14   15                                                       
CONECT   35   15   33   37                                                  
CONECT   36    8   10   32                                                  
CONECT   37   17   18   35                                                  
CONECT   38   16   17                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

COMPND    HMDB0004220
HETATM    1  N1  UNL     1      -9.531   1.629   1.175  1.00  0.00           N  
HETATM    2  C1  UNL     1      -8.357   0.893   1.405  1.00  0.00           C  
HETATM    3  N2  UNL     1      -7.846   0.782   2.639  1.00  0.00           N  
HETATM    4  C2  UNL     1      -6.713   0.082   2.876  1.00  0.00           C  
HETATM    5  N3  UNL     1      -6.085  -0.515   1.854  1.00  0.00           N  
HETATM    6  C3  UNL     1      -6.525  -0.455   0.590  1.00  0.00           C  
HETATM    7  C4  UNL     1      -7.693   0.269   0.365  1.00  0.00           C  
HETATM    8  N4  UNL     1      -7.910   0.166  -0.978  1.00  0.00           N  
HETATM    9  C5  UNL     1      -6.918  -0.582  -1.506  1.00  0.00           C  
HETATM   10  N5  UNL     1      -6.071  -0.961  -0.548  1.00  0.00           N  
HETATM   11  C6  UNL     1      -4.885  -1.766  -0.730  1.00  0.00           C  
HETATM   12  O1  UNL     1      -4.069  -1.692   0.368  1.00  0.00           O  
HETATM   13  C7  UNL     1      -2.751  -1.731   0.012  1.00  0.00           C  
HETATM   14  C8  UNL     1      -2.041  -0.430   0.433  1.00  0.00           C  
HETATM   15  O2  UNL     1      -2.104  -0.209   1.784  1.00  0.00           O  
HETATM   16  P1  UNL     1      -1.339   1.246   2.154  1.00  0.00           P  
HETATM   17  O3  UNL     1      -1.265   1.304   3.683  1.00  0.00           O  
HETATM   18  O4  UNL     1      -2.275   2.538   1.581  1.00  0.00           O  
HETATM   19  O5  UNL     1       0.255   1.345   1.573  1.00  0.00           O  
HETATM   20  C9  UNL     1       0.625   1.668   0.296  1.00  0.00           C  
HETATM   21  O6  UNL     1      -0.264   1.922  -0.560  1.00  0.00           O  
HETATM   22  C10 UNL     1       2.076   1.728  -0.122  1.00  0.00           C  
HETATM   23  C11 UNL     1       2.607   0.335  -0.023  1.00  0.00           C  
HETATM   24  C12 UNL     1       4.062   0.206  -0.432  1.00  0.00           C  
HETATM   25  C13 UNL     1       4.874   1.102   0.439  1.00  0.00           C  
HETATM   26  C14 UNL     1       6.335   1.118   0.204  1.00  0.00           C  
HETATM   27  S1  UNL     1       6.808   1.617  -1.486  1.00  0.00           S  
HETATM   28  C15 UNL     1       7.980   0.240  -1.814  1.00  0.00           C  
HETATM   29  C16 UNL     1       7.517  -0.768  -0.822  1.00  0.00           C  
HETATM   30  N6  UNL     1       8.702  -1.533  -0.409  1.00  0.00           N  
HETATM   31  C17 UNL     1       9.254  -0.836   0.699  1.00  0.00           C  
HETATM   32  O7  UNL     1      10.414  -0.934   1.197  1.00  0.00           O  
HETATM   33  N7  UNL     1       8.288   0.060   1.237  1.00  0.00           N  
HETATM   34  C18 UNL     1       7.091  -0.125   0.440  1.00  0.00           C  
HETATM   35  C19 UNL     1      -2.680  -1.747  -1.500  1.00  0.00           C  
HETATM   36  O8  UNL     1      -2.565  -3.065  -1.931  1.00  0.00           O  
HETATM   37  C20 UNL     1      -4.054  -1.219  -1.854  1.00  0.00           C  
HETATM   38  O9  UNL     1      -4.467  -1.701  -3.103  1.00  0.00           O  
HETATM   39  H1  UNL     1     -10.413   1.124   0.911  1.00  0.00           H  
HETATM   40  H2  UNL     1      -9.598   2.664   1.250  1.00  0.00           H  
HETATM   41  H3  UNL     1      -6.369   0.040   3.885  1.00  0.00           H  
HETATM   42  H4  UNL     1      -6.885  -0.799  -2.566  1.00  0.00           H  
HETATM   43  H5  UNL     1      -5.138  -2.819  -1.008  1.00  0.00           H  
HETATM   44  H6  UNL     1      -2.237  -2.576   0.466  1.00  0.00           H  
HETATM   45  H7  UNL     1      -0.978  -0.582   0.128  1.00  0.00           H  
HETATM   46  H8  UNL     1      -2.480   0.356  -0.178  1.00  0.00           H  
HETATM   47  H9  UNL     1      -1.689   3.277   1.255  1.00  0.00           H  
HETATM   48  H10 UNL     1       2.133   2.080  -1.180  1.00  0.00           H  
HETATM   49  H11 UNL     1       2.552   2.456   0.575  1.00  0.00           H  
HETATM   50  H12 UNL     1       1.998  -0.323  -0.664  1.00  0.00           H  
HETATM   51  H13 UNL     1       2.458   0.004   1.027  1.00  0.00           H  
HETATM   52  H14 UNL     1       4.336  -0.856  -0.161  1.00  0.00           H  
HETATM   53  H15 UNL     1       4.210   0.377  -1.498  1.00  0.00           H  
HETATM   54  H16 UNL     1       4.534   2.179   0.378  1.00  0.00           H  
HETATM   55  H17 UNL     1       4.698   0.803   1.489  1.00  0.00           H  
HETATM   56  H18 UNL     1       6.760   1.929   0.864  1.00  0.00           H  
HETATM   57  H19 UNL     1       8.995   0.625  -1.608  1.00  0.00           H  
HETATM   58  H20 UNL     1       7.856  -0.156  -2.842  1.00  0.00           H  
HETATM   59  H21 UNL     1       6.762  -1.444  -1.278  1.00  0.00           H  
HETATM   60  H22 UNL     1       9.090  -2.401  -0.811  1.00  0.00           H  
HETATM   61  H23 UNL     1       8.354   0.724   2.017  1.00  0.00           H  
HETATM   62  H24 UNL     1       6.419  -0.838   0.976  1.00  0.00           H  
HETATM   63  H25 UNL     1      -1.883  -1.106  -1.892  1.00  0.00           H  
HETATM   64  H26 UNL     1      -3.124  -3.681  -1.413  1.00  0.00           H  
HETATM   65  H27 UNL     1      -4.093  -0.127  -1.808  1.00  0.00           H  
HETATM   66  H28 UNL     1      -4.747  -0.911  -3.633  1.00  0.00           H  
CONECT    1    2   39   40
CONECT    2    3    3    7
CONECT    3    4
CONECT    4    5    5   41
CONECT    5    6
CONECT    6    7    7   10
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   42
CONECT   10   11
CONECT   11   12   37   43
CONECT   12   13
CONECT   13   14   35   44
CONECT   14   15   45   46
CONECT   15   16
CONECT   16   17   17   18   19
CONECT   18   47
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   48   49
CONECT   23   24   50   51
CONECT   24   25   52   53
CONECT   25   26   54   55
CONECT   26   27   34   56
CONECT   27   28
CONECT   28   29   57   58
CONECT   29   30   34   59
CONECT   30   31   60
CONECT   31   32   32   33
CONECT   33   34   61
CONECT   34   62
CONECT   35   36   37   63
CONECT   36   64
CONECT   37   38   65
CONECT   38   66
END

HMDB0004220
     RDKit          3D
Biotinyl-5'-AMP
 66 70  0  0  0  0  0  0  0  0999 V2000
   -9.5314    1.6288    1.1748 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3567    0.8931    1.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8460    0.7821    2.6394 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7128    0.0819    2.8763 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0846   -0.5152    1.8539 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5253   -0.4552    0.5900 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6931    0.2694    0.3650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9099    0.1657   -0.9781 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9176   -0.5820   -1.5056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0709   -0.9614   -0.5477 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8848   -1.7664   -0.7295 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0689   -1.6916    0.3676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7515   -1.7314    0.0123 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0413   -0.4303    0.4329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1044   -0.2088    1.7839 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3393    1.2462    2.1537 P   0  0  0  0  0  5  0  0  0  0  0  0
   -1.2653    1.3044    3.6829 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2749    2.5379    1.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2552    1.3447    1.5732 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6252    1.6682    0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2643    1.9221   -0.5599 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0762    1.7282   -0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6075    0.3354   -0.0233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0619    0.2063   -0.4320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8735    1.1024    0.4386 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3350    1.1181    0.2044 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8084    1.6168   -1.4862 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9801    0.2395   -1.8139 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.7680   -0.8217 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7020   -1.5326   -0.4091 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2543   -0.8360    0.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4137   -0.9342    1.1970 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2881    0.0605    1.2372 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0915   -0.1254    0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6802   -1.7469   -1.4997 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5650   -3.0652   -1.9309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0542   -1.2188   -1.8541 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4670   -1.7011   -3.1033 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4132    1.1241    0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5980    2.6637    1.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3692    0.0403    3.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8851   -0.7987   -2.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384   -2.8192   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367   -2.5761    0.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9779   -0.5816    0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4803    0.3560   -0.1776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6892    3.2773    1.2546 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1332    2.0801   -1.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5519    2.4560    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9984   -0.3230   -0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4580    0.0039    1.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3357   -0.8560   -0.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102    0.3766   -1.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5338    2.1793    0.3779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6982    0.8035    1.4891 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7602    1.9286    0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9948    0.6249   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8562   -0.1561   -2.8424 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7619   -1.4436   -1.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0898   -2.4012   -0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3538    0.7235    2.0169 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4192   -0.8383    0.9759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8829   -1.1059   -1.8923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242   -3.6809   -1.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0932   -0.1266   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7469   -0.9115   -3.6335 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
 30 31  1  0
 31 32  2  0
 31 33  1  0
 33 34  1  0
 13 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
  7  2  1  0
 37 11  1  0
 10  6  1  0
 34 26  1  0
 34 29  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  9 42  1  0
 11 43  1  6
 13 44  1  1
 14 45  1  0
 14 46  1  0
 18 47  1  0
 22 48  1  0
 22 49  1  0
 23 50  1  0
 23 51  1  0
 24 52  1  0
 24 53  1  0
 25 54  1  0
 25 55  1  0
 26 56  1  1
 28 57  1  0
 28 58  1  0
 29 59  1  0
 30 60  1  0
 33 61  1  0
 34 62  1  0
 35 63  1  1
 36 64  1  0
 37 65  1  6
 38 66  1  0
M  END

Synonyms

Value	Source
(+)-Biotinyl 5'-adenylate	HMDB
5'-Adenylic acid anhydride with biotin	HMDB
5'-Adenylic acid monoanhydride with biotin	HMDB
b-AMP	HMDB
beta-AMP	HMDB
Bio-5-AMP	HMDB
Biotin anhydride with 5'-adenylic acid	HMDB
Biotinoyl 5'-adenylate	HMDB
Biotinyl 5'-AMP	HMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoate	HMDB
[3AS-(3aa,4b,6aa)]-5'-adenylic acid monoanhydride with hexahydro-2-oxo-1H-thieno[3,4-D]imidazole-4-pentanoic acid	HMDB

Molecular Formula

C₂₀H₂₈N₇O₉PS

Average Mass

573.517

Monoisotopic Mass

573.140682731

IUPAC Name

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

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({5-[(4S)-2-oxo-hexahydrothieno[3,4-d]imidazolidin-4-yl]pentanoyl}oxy)phosphinic acid

CAS Registry Number

4130-20-5

SMILES

NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](COP(O)(=O)OC(=O)CCCC[C@@H]2SCC3NC(=O)NC23)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C20H28N7O9PS/c21-17-14-18(23-7-22-17)27(8-24-14)19-16(30)15(29)10(35-19)5-34-37(32,33)36-12(28)4-2-1-3-11-13-9(6-38-11)25-20(31)26-13/h7-11,13,15-16,19,29-30H,1-6H2,(H,32,33)(H2,21,22,23)(H2,25,26,31)/t9?,10-,11+,13?,15-,16-,19-/m1/s1

InChI Key

UTQCSTJVMLODHM-CFYKWCKVSA-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
Biotin_derivative
Biotin
Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Thienoimidazolidine
Acyl phosphate
Aminopyrimidine
Monoalkyl phosphate
Imidazolidinone
Imidolactam
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Pyrimidine
Thiophene
Thiolane
Tetrahydrofuran
Azole
Imidazole
Imidazolidine
Heteroaromatic compound
Amino acid or derivatives
Carbonic acid derivative
Urea
Secondary alcohol
1,2-diol
Carboxylic acid salt
Dialkylthioether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Thioether
Organoheterocyclic compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organic salt
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Organic oxide
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.24 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-4.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	233.27 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	130.63 m³·mol⁻¹	ChemAxon
Polarizability	53.92 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-6729030000-2cb82379b8e96b597b13	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00kb-9733703000-98bae5a17ded03704629	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Biotinyl-5'-AMP,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_15) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_16) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0942030000-e61e914c7ef0f87ef7ce	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0910000000-90a339c73ce7d6e18307	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2900000000-4473efe13a9fdcd356f6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00c0-2309030000-db991b74538e5511fc08	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-7902000000-c38c4f3a31b23503bb6d	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-9400000000-f14ea50608a771c5ffc0	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0101090000-26c429c0d542be98a853	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0940020000-3590ed25fbf2aee9ac0c	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0931010000-189f936a74fee5be25d1	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0001090000-4427dd4df762a2ebe889	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00b9-9004080000-1810ce9ed7993ec252eb	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01t9-9200000000-0a1f3c98da5c89d7c119	2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192163	Biotin--protein ligase	Enzyme	P50747	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0000370	Biotin	Biotinyl-5'-AMP	holocarboxylase synthetase (biotin-(proprionyl-CoA-carboxylase (ATP-hydrolysing)) ligase)	VMH; KEGG	12459313 7842009
MMDBr0000371	Biotin	Biotinyl-5'-AMP	holocarboxylase synthetase (biotin-(proprionyl-CoA-carboxylase (ATP-hydrolysing)) ligase)	VMH; KEGG	12459313 7842009
MMDBr0007277	Biotinyl-5'-AMP	Biotin	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	105	Human feces; Human sputum; Human pleural fluid plaque; Human ; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	248	Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Human stool	Metabolic reconstruction
Bacteria	Actinobacteria	59	Human feces; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	71	Human feces; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	15	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004220

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023336

KNApSAcK ID

Not Available

Chemspider ID

389681

KEGG Compound ID

C05921

BioCyc ID

Not Available

BiGG ID

46920

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440839

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Solorzano-Vargas RS, Pacheco-Alvarez D, Leon-Del-Rio A: Holocarboxylase synthetase is an obligate participant in biotin-mediated regulation of its own expression and of biotin-dependent carboxylases mRNA levels in human cells. Proc Natl Acad Sci U S A. 2002 Apr 16;99(8):5325-30. doi: 10.1073/pnas.082097699. [PubMed:11959985 ]
Pacheco-Alvarez D, Solorzano-Vargas RS, Gonzalez-Noriega A, Michalak C, Zempleni J, Leon-Del-Rio A: Biotin availability regulates expression of the sodium-dependent multivitamin transporter and the rate of biotin uptake in HepG2 cells. Mol Genet Metab. 2005 Aug;85(4):301-7. doi: 10.1016/j.ymgme.2005.04.001. [PubMed:15905112 ]

Showing metabocard for Biotinyl-5'-AMP (MMDBc0029821)

MOL for #<Metabolite:0x00007fece11538c8>

3D MOL for #<Metabolite:0x00007fece11538c8>

3D SDF for #<Metabolite:0x00007fece11538c8>

3D-SDF for #<Metabolite:0x00007fece11538c8>

PDB for #<Metabolite:0x00007fece11538c8>

3D PDB for #<Metabolite:0x00007fece11538c8>

SMILES for #<Metabolite:0x00007fece11538c8>

INCHI for #<Metabolite:0x00007fece11538c8>

Structure for #<Metabolite:0x00007fece11538c8>

3D Structure for #<Metabolite:0x00007fece11538c8>