NP-MRD: Showing NP-Card for Biotinyl-5'-AMP (NP0087154)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:41:39 UTC

Updated at

2022-05-11 16:41:40 UTC

NP-MRD ID

NP0087154

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Biotinyl-5'-AMP

Description

Biotinyl-5'-AMP, also known as b-AMP or bio-5-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. Biotinyl-5'-AMP is a strong basic compound (based on its pKa). 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. Biotinyl-5'-AMP exists in all living organisms, ranging from bacteria to humans. In humans, biotinyl-5'-AMP is involved in biotin metabolism. Biotinyl-5'-AMP was first documented in 2002 (PMID: 11959985). 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).

Structure

MOL 3D MOL SDF 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
 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

     RDKit          3D

 66 70  0  0  0  0  0  0  0  0999 V2000
  -10.0046    3.0949    1.5758 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2665    2.3316    0.6507 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8010    1.7945   -0.4894 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1023    1.0083   -1.3368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8257    0.7111   -1.1016 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2565    1.2119   -0.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9178    2.0210    0.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0350    2.3119    1.8144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8641    1.7187    1.5412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9664    0.9978    0.3827 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    0.1337   -0.1306 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1491    0.3706   -1.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4912   -0.8774   -1.1000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1280   -1.0860   -1.5379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4334   -0.0950   -0.7373 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3565   -0.9261    0.2180 P   0  0  1  0  0  5  0  0  0  0  0  0
   -0.3961   -0.2056    1.6300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9242   -2.5125    0.4908 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2371   -0.9244   -0.2111 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8897    0.3341   -0.3589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729    1.3869   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3457    0.1829   -0.6712 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125   -0.4641    0.6173 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5351   -1.7511    0.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6224   -1.2867   -0.8602 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8627   -0.9489   -0.1111 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7371    0.2087    1.2510 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.2970    1.1047    1.0312 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8594    0.4642   -0.2305 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.2562    1.6206   -1.0507 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0402    2.1634   -1.5148 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8551    3.3048   -2.0211 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0012    1.1749   -1.3114 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7201   -0.0458   -1.0514 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5953   -1.8206   -1.4134 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3006   -3.1371   -1.0157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6458   -1.2392   -0.4373 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.6082   -2.0196    0.7124 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8941    4.1124    1.6666 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7020    2.6052    2.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5668    0.6035   -2.2209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9755    1.8112    2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2866   -0.1249    0.7439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3727   -0.9893    0.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651   -0.8141   -2.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -2.0342   -1.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692   -3.1990    0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3711   -0.5376   -1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7465    1.1666   -0.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -0.7057    1.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5568    0.2691    1.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0050   -2.2377    0.9775 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7325   -2.3455   -0.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2904   -0.4104   -1.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7995   -2.0883   -1.6070 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4529   -1.8453    0.0634 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9224    0.8732    1.9011 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1076    2.1969    0.8847 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6580   -0.2322   -0.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2331    1.9321   -1.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9996    1.4304   -1.3679 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0427   -0.6273   -1.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9094   -1.7191   -2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3349   -3.2522   -0.8615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6220   -1.1938   -0.8724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8044   -2.9546    0.5377 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
 16 15  1  6
 16 18  1  0
 16 17  2  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  1
 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  1
 30 60  1  0
 33 61  1  0
 34 62  1  6
 35 63  1  6
 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
  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
 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>
NP0087154

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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

Chemical Formula

C₂₀H₂₈N₇O₉PS

Average Mass

573.5170 Da

Monoisotopic Mass

573.14068 Da

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

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0004220

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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 ]

Showing NP-Card for Biotinyl-5'-AMP (NP0087154)

MOL for NP0087154 (Biotinyl-5'-AMP)

3D MOL for NP0087154 (Biotinyl-5'-AMP)

3D SDF for NP0087154 (Biotinyl-5'-AMP)

3D-SDF for NP0087154 (Biotinyl-5'-AMP)

PDB for NP0087154 (Biotinyl-5'-AMP)

3D PDB for NP0087154 (Biotinyl-5'-AMP)

SMILES for NP0087154 (Biotinyl-5'-AMP)

INCHI for NP0087154 (Biotinyl-5'-AMP)

Structure for NP0087154 (Biotinyl-5'-AMP)

3D Structure for NP0087154 (Biotinyl-5'-AMP)