NP-MRD: Showing NP-Card for {[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0234472)

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Record Information

Version

1.0

Created at

2022-09-06 16:31:38 UTC

Updated at

2022-09-06 16:31:38 UTC

NP-MRD ID

NP0234472

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid

Description

[({[3,4-Dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety. {[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid is found in Eremothecium ashbyi. [({[3,4-Dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171517402D          

 39 42  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -2.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -3.4463    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -3.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -3.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1857   -4.2310    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7377   -4.8441    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3508   -4.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1246   -5.3961    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2897   -5.4571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0348   -6.2418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8518   -6.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3597   -5.7065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3064   -5.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -6.2916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3645   -7.1161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0641   -7.5533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3639   -7.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3927   -8.3279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0636   -7.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7920   -7.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -0.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    0.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
M  END

     RDKit          3D

 64 67  0  0  0  0  0  0  0  0999 V2000
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   -9.0998   -0.0781   -0.4740 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6497   -1.8522    0.9784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7311   -2.5831    1.6196 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5427   -2.0082    1.3712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6845   -0.9290    0.5871 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6441   -0.0468    0.1008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5718   -0.8033   -0.2821 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4566   -0.4177    0.4117 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2698   -0.4994   -0.5164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.1320    0.0754 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1300   -0.2875   -1.1159 P   0  0  1  0  0  5  0  0  0  0  0  0
    0.9512   -1.6148   -1.8114 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8270    0.9369   -2.2625 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653   -0.0918   -0.4793 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7076    0.3509   -1.7293 P   0  0  1  0  0  5  0  0  0  0  0  0
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    5.2442   -0.2133   -1.6177 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7314   -0.6761   -0.4449 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0174   -1.8479    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7255   -2.1341    1.3689 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.1325   -0.7121 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9645   -0.7350    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2436    0.7623    0.1908 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.1102    1.0471   -0.8365 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9010    1.4247   -0.0836 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.8167    2.6921    0.4497 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8656    0.4737    0.5338 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.6631    1.1559    0.6158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6956    0.9888    0.8941 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3304    1.8981   -0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2150    0.9534    1.1105 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7608    2.2154    0.8621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0414   -1.9533    0.8635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6054   -2.9004    1.4594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7619   -1.0746    0.1438 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7610    1.1694   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2948    1.3296   -2.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5728   -2.3571    1.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9928    0.5154   -0.8103 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2836   -1.0676    1.3122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1867   -1.5705   -0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5206    0.0810   -1.4271 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3024    1.7818   -2.0164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9504    2.4425   -2.5650 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9835   -1.6891    0.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1835   -2.7329   -0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8996   -3.0931    1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8103   -1.0884    1.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9415   -1.2031   -0.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5716    1.1070    1.1817 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9548    0.4021   -1.5841 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7577    1.3966   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7423    3.3292   -0.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2207    0.1391    1.5329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8961    2.0776    0.9574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1688    1.2146    1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5663    2.8188    0.1602 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3789    0.6506    2.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4283    2.3817    1.6013 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8064   -1.1565    0.0618 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  1  0
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 10 11  1  0
 11 12  1  0
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 14 13  1  1
 14 16  1  0
 14 15  2  0
 14 17  1  0
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 18 20  1  0
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 22 21  1  6
 22 23  1  0
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 29 30  1  0
 29 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
  5 37  1  0
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 39  2  1  0
  8  4  1  0
 35  9  1  0
 31 22  1  0
  1 40  1  0
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  9 43  1  6
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 16 47  1  0
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 31 58  1  1
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 33 60  1  1
 34 61  1  0
 35 62  1  1
 36 63  1  0
 39 64  1  0
M  END


  Mrv1533004171517402D          

 39 42  0  0  0  0            999 V2000
    2.7845    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -2.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6955   -2.6617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4406   -3.4463    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2252   -3.7013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3440   -3.1914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7920   -7.4536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -1.0091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.4940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1831   -0.1841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505    0.3009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 11 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
  9 35  1  0  0  0  0
 35 36  1  0  0  0  0
  5 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
  2 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234472

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC2=C(N=CN2C2OC(COP(O)(=O)OP(O)(=O)OC3(CO)OCC(O)C(O)C3O)C(O)C2O)C(=O)N1

> <INCHI_IDENTIFIER>
InChI=1S/C16H25N5O16P2/c17-15-19-12-7(13(28)20-15)18-4-21(12)14-10(26)9(25)6(35-14)2-34-38(29,30)37-39(31,32)36-16(3-22)11(27)8(24)5(23)1-33-16/h4-6,8-11,14,22-27H,1-3H2,(H,29,30)(H,31,32)(H3,17,19,20,28)

> <INCHI_KEY>
NZGNDDIZKFLDTC-UHFFFAOYSA-N

> <FORMULA>
C16H25N5O16P2

> <MOLECULAR_WEIGHT>
605.343

> <EXACT_MASS>
605.077153741

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
49.79983936899781

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

> <ALOGPS_LOGP>
-1.39

> <JCHEM_LOGP>
-5.113044233000001

> <ALOGPS_LOGS>
-1.82

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.162528856285586

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7091019060886268

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5272119945774927

> <JCHEM_POLAR_SURFACE_AREA>
327.42999999999995

> <JCHEM_REFRACTIVITY>
118.94870000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxyphosphoryl}oxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  N   UNK     0       5.198   1.303   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.530   1.303   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.268   4.089   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -0.268   1.597   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.161  -1.114   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.744  -2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.268  -3.824   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.298  -4.969   0.000  0.00  0.00           O+0
HETATM   14  P   UNK     0      -0.822  -6.433   0.000  0.00  0.00           P+0
HETATM   15  O   UNK     0      -2.287  -6.909   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.642  -5.957   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.347  -7.898   0.000  0.00  0.00           O+0
HETATM   18  P   UNK     0      -1.377  -9.042   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      -2.521  -8.012   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.233 -10.073   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.407 -10.187   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.932 -11.651   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.457 -11.866   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.405 -10.652   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.572 -10.928   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.734 -11.744   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.680 -13.283   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.986 -14.100   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.679 -14.006   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -0.733 -15.545   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.985 -13.190   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -3.345 -13.913   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.208  -1.884   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.454  -2.789   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.208  -0.344   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -3.454   0.562   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0       3.864   3.613   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   35                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   33                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14   18                                                       
CONECT   18   17   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18   22                                                       
CONECT   22   21   23   25   31                                             
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   22   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   22   32                                                  
CONECT   32   31                                                            
CONECT   33   11   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    9   36                                                  
CONECT   36   35                                                            
CONECT   37    5   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37    2                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
[({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy})phosphinate	Generator

Chemical Formula

C₁₆H₂₅N₅O₁₆P₂

Average Mass

605.3430 Da

Monoisotopic Mass

605.07715 Da

IUPAC Name

{[5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

Traditional Name

[5-(2-amino-6-oxo-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy({hydroxy[3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxyphosphoryl}oxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

NC1=NC2=C(N=CN2C2OC(COP(O)(=O)OP(O)(=O)OC3(CO)OCC(O)C(O)C3O)C(O)C2O)C(=O)N1

InChI Identifier

InChI=1S/C16H25N5O16P2/c17-15-19-12-7(13(28)20-15)18-4-21(12)14-10(26)9(25)6(35-14)2-34-38(29,30)37-39(31,32)36-16(3-22)11(27)8(24)5(23)1-33-16/h4-6,8-11,14,22-27H,1-3H2,(H,29,30)(H,31,32)(H3,17,19,20,28)

InChI Key

NZGNDDIZKFLDTC-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Eremothecium ashbyi	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as saccharolipids. Saccharolipids are compounds in which fatty acids are linked directly to a sugar backbone, forming structures that are compatible with membrane bilayers. In the saccharolipids, a sugar substitutes for the glycerol backbone that is present in glycerolipids and glycerophospholipids. The most familiar saccharolipids contain an acylated glucosamine. In contrast to others glycolipids, the fatty acid is not glycosidically linked to the sugar moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Saccharolipids

Sub Class

Not Available

Direct Parent

Saccharolipids

Alternative Parents

Substituents

Saccharolipid
Terpene glycoside
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Fatty alcohol ester
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Oxane
Monosaccharide
Fatty acyl
Secondary alcohol
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	-1.4	ALOGPS
logP	-5.1	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	1.71	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	327.43 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	118.95 m³·mol⁻¹	ChemAxon
Polarizability	49.8 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid (NP0234472)

MOL for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D MOL for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D SDF for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D-SDF for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

PDB for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D PDB for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

SMILES for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

INCHI for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

Structure for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)

3D Structure for NP0234472 ({[3,4-dihydroxy-5-(6-hydroxy-2-imino-3h-purin-9-yl)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy([3,4,5-trihydroxy-2-(hydroxymethyl)oxan-2-yl]oxy)phosphinic acid)