NP-MRD: Showing NP-Card for [(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid (NP0171066)

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Record Information

Version

2.0

Created at

2022-09-03 07:25:24 UTC

Updated at

2022-09-03 07:25:24 UTC

NP-MRD ID

NP0171066

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid

Description

[({[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. [(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid is found in Streptomyces fradiae. Based on a literature review very few articles have been published on [({[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032209252D          

 35 37  0  0  1  0            999 V2000
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5253   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -6.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7553   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -6.2195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9605   -6.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960   -7.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -8.3081    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -8.7930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437   -7.8232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -8.9755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617   -9.7292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154   -9.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081  -10.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973  -10.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124  -11.1503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8479  -11.9040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630  -12.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986  -13.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425  -12.4852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0576  -13.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070  -11.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135  -11.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919  -11.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3563  -10.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -5.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 30  1  0  0  0  0
  5 30  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END

     RDKit          3D

 62 64  0  0  0  0  0  0  0  0999 V2000
   -8.9737    0.9141    0.4671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0077   -0.1521    0.2802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6351    0.1806    0.4657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7172   -0.7456    0.2751 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3478   -0.3947    0.1699 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3212    0.5242   -1.1589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8837    0.9242   -1.0686 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1616   -0.0207   -1.8157 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6471    0.7766    0.3971 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6071    1.6847    0.9039 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5919    1.5313   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7791    0.8658    0.5887 P   0  0  2  0  0  5  0  0  0  0  0  0
    0.8822   -0.5918   -0.0672 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.5226    2.2014 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2249    1.5537    0.2397 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7200    1.0637   -1.3150 P   0  0  2  0  0  5  0  0  0  0  0  0
    2.1086    1.9858   -2.3493 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1898   -0.5234   -1.6386 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3950    0.9942   -1.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433    0.5733   -0.1048 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.1010   -0.8056   -0.2452 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5821   -1.2517    0.9680 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.4647   -2.7757    1.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0372   -0.8579    1.1365 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.7841   -1.9252    0.6155 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.3546    0.2578 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3732   -0.0663   -1.1091 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0672    1.3155    0.3347 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3180    2.3250   -0.5951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8530    0.5622    1.0017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0899   -2.0104   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2088   -2.9107   -0.2496 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4237   -2.3132   -0.2644 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3888   -1.4143   -0.0893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7374   -1.7528   -0.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5101    0.7485    1.4207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7728    0.7535   -0.3200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5287    1.8963    0.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3354    1.1462    0.7736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6334   -1.1719   -0.0226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5746   -0.0896   -2.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9829    1.3793   -0.9542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7001    1.9472   -1.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7609   -0.7986   -2.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1399   -0.3044    0.5233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2296    1.6203    1.8853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8972    2.8010    0.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    1.2990    2.7762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8882   -1.2049   -1.4694 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0280    0.6459    0.6144 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -0.8760    1.8051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9414   -3.1447    1.9509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8397   -3.2508    0.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3778   -3.0287    1.0971 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2240   -0.6877    2.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9047   -1.8323   -0.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1397    0.9382    0.5602 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2962    0.2323   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6105    0.2256   -1.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9963    1.8110    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4538    2.5864   -0.9975 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0103   -1.7815   -1.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 16 19  1  1
 16 18  1  0
 16 17  2  0
 16 15  1  0
 12 15  1  1
 12 14  1  0
 12 13  2  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9 30  1  0
 30  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 34  1  0
 34 35  1  0
 34 33  2  0
 33 31  1  0
 31 32  2  0
 20 28  1  0
 28 29  1  0
 28 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
 24 22  1  0
  7  9  1  0
 31  4  1  0
 23 52  1  0
 23 53  1  0
 23 54  1  0
 22 51  1  1
 20 50  1  1
 18 49  1  0
 14 48  1  0
 10 46  1  0
 10 47  1  0
  9 45  1  6
  5 40  1  6
  6 41  1  0
  6 42  1  0
  7 43  1  6
  8 44  1  0
  3 39  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
 35 62  1  0
 28 60  1  1
 29 61  1  0
 26 57  1  1
 27 58  1  0
 27 59  1  0
 24 55  1  1
 25 56  1  0
M  END


  Mrv1652309032209252D          

 35 37  0  0  1  0            999 V2000
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5253   -5.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -6.2195    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7553   -6.8870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -6.2195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9605   -6.8870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2960   -7.6407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8111   -8.3081    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -8.7930    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437   -7.8232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3262   -8.9755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6617   -9.7292    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.4154   -9.3937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9081  -10.0648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9973  -10.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5124  -11.1503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8479  -11.9040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3630  -12.5714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986  -13.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5425  -12.4852    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0576  -13.1526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2070  -11.7315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135  -11.6453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919  -11.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3563  -10.3104    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1904   -5.4349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 20 28  1  0  0  0  0
 28 29  1  0  0  0  0
  9 30  1  0  0  0  0
  5 30  1  0  0  0  0
  4 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
  2 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0171066

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(O)=NC2=O)C(O)C(N)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)11(17)12(21)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7?,8-,9+,10+,11?,12+,13?,15+/m0/s1

> <INCHI_KEY>
KVYJLJOGNUNRJK-OIECSZRWSA-N

> <FORMULA>
C16H27N3O14P2

> <MOLECULAR_WEIGHT>
547.347

> <EXACT_MASS>
547.096826557

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.46372380599596

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[({[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid

> <ALOGPS_LOGP>
-1.64

> <JCHEM_LOGP>
-3.6059207870481824

> <ALOGPS_LOGS>
-1.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.1760399805824115

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.7321592530371008

> <JCHEM_PKA_STRONGEST_BASIC>
9.127652267917341

> <JCHEM_POLAR_SURFACE_AREA>
260.36

> <JCHEM_REFRACTIVITY>
109.7377

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy([(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       5.335  -7.700   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.581 -10.145   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.105 -11.610   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.010 -12.856   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.565 -11.610   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.660 -12.856   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.286 -14.263   0.000  0.00  0.00           O+0
HETATM   12  P   UNK     0       3.381 -15.508   0.000  0.00  0.00           P+0
HETATM   13  O   UNK     0       4.627 -16.414   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.135 -14.603   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.476 -16.754   0.000  0.00  0.00           O+0
HETATM   16  P   UNK     0       3.102 -18.161   0.000  0.00  0.00           P+0
HETATM   17  O   UNK     0       4.509 -17.535   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.695 -18.788   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.728 -19.568   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.823 -20.814   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.449 -22.221   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.544 -23.467   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.171 -24.874   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.013 -23.306   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.108 -24.552   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.386 -21.899   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -1.145 -21.738   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0       1.292 -20.653   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.665 -19.246   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       4.089 -10.145   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   33  N   UNK     0       4.001  -5.390   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   28                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   20   29                                                  
CONECT   29   28                                                            
CONECT   30    9    5                                                       
CONECT   31    4   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
[({[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinate	Generator

Chemical Formula

C₁₆H₂₇N₃O₁₄P₂

Average Mass

547.3470 Da

Monoisotopic Mass

547.09683 Da

IUPAC Name

[({[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphinic acid

Traditional Name

{[(2R,5S)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy(hydroxy)phosphoryl}oxy([(2R,3S,5R)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

CC1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H](C[C@@H]2O)N2C=C(C)C(O)=NC2=O)C(O)C(N)[C@@H]1O

InChI Identifier

InChI=1S/C16H27N3O14P2/c1-6-4-19(16(24)18-14(6)23)10-3-8(20)9(31-10)5-29-34(25,26)33-35(27,28)32-15-13(22)11(17)12(21)7(2)30-15/h4,7-13,15,20-22H,3,5,17H2,1-2H3,(H,25,26)(H,27,28)(H,18,23,24)/t7?,8-,9+,10+,11?,12+,13?,15+/m0/s1

InChI Key

KVYJLJOGNUNRJK-OIECSZRWSA-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
Streptomyces fradiae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleotides

Sub Class

Pyrimidine nucleotide sugars

Direct Parent

Pyrimidine nucleotide sugars

Alternative Parents

Substituents

Pyrimidine nucleotide sugar
Pentose phosphate
Organic pyrophosphate
Monosaccharide phosphate
Hydroxypyrimidine
Monoalkyl phosphate
Amino saccharide
Pyrimidone
Alkyl phosphate
Pyrimidine
Phosphoric acid ester
Oxane
Organic phosphoric acid derivative
Monosaccharide
Hydropyrimidine
Heteroaromatic compound
Tetrahydrofuran
Secondary alcohol
1,2-aminoalcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	-1.6	ALOGPS
logP	-3.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	260.36 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	109.74 m³·mol⁻¹	ChemAxon
Polarizability	46.46 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

162820759

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid (NP0171066)

MOL for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

3D MOL for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

3D SDF for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

3D-SDF for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

PDB for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

3D PDB for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

SMILES for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

INCHI for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

Structure for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)

3D Structure for NP0171066 ([(2r,5s)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy([hydroxy([(2r,3s,5r)-3-hydroxy-5-(4-hydroxy-5-methyl-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy)phosphoryl]oxy)phosphinic acid)