NP-MRD: Showing NP-Card for Phosmidosine B (NP0023147)

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Record Information

Version

2.0

Created at

2021-01-06 08:15:55 UTC

Updated at

2021-07-15 17:40:58 UTC

NP-MRD ID

NP0023147

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phosmidosine B

Provided By

NPAtlas

Description

Phosmidosine B is found in Streptomyces. Phosmidosine B was first documented in 1996 (PMID: 8641999). Based on a literature review very few articles have been published on (2S)-N-({[(2R,3S,4R,5R)-5-(6-amino-8-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)pyrrolidine-2-carboximidic acid (PMID: 12003538).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105393D          

 53 56  0  0  0  0            999 V2000
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   -7.1791    0.5563   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -8.2049    1.5228   -0.9192 N   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242105393D          

 53 56  0  0  0  0            999 V2000
   -8.2049    1.5228   -0.9192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1791    0.5563   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5549    1.7301   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782   -0.9433   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8520    0.2049   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.0242   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344   -0.4647   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9848    0.0120    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525   -1.4270    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551   -0.1511    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -1.4943   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -3.2376    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -2.1164    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650   -2.7629    2.5824 H   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
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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  1  0  0  0  0
 15 16  1  0  0  0  0
 17 16  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
  7  2  1  0  0  0  0
 30 12  1  0  0  0  0
 11  6  1  0  0  0  0
 27 23  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  4 34  1  0  0  0  0
  8 35  1  0  0  0  0
 12 36  1  1  0  0  0
 14 37  1  1  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
 19 40  1  0  0  0  0
 20 41  1  0  0  0  0
 23 42  1  1  0  0  0
 24 43  1  0  0  0  0
 24 44  1  0  0  0  0
 25 45  1  0  0  0  0
 25 46  1  0  0  0  0
 26 47  1  0  0  0  0
 26 48  1  0  0  0  0
 27 49  1  0  0  0  0
 28 50  1  6  0  0  0
 29 51  1  0  0  0  0
 30 52  1  6  0  0  0
 31 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023147

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])[C@@]([H])(O[C@]([H])(C([H])([H])O[P@@](=O)(O[H])N([H])C(=O)[C@@]2([H])N([H])C([H])([H])C([H])([H])C2([H])[H])[C@@]1([H])O[H])N1C(=O)N([H])C2=C1N=C([H])N=C2N([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C15H22N7O8P/c16-11-8-12(19-5-18-11)22(15(26)20-8)14-10(24)9(23)7(30-14)4-29-31(27,28)21-13(25)6-2-1-3-17-6/h5-7,9-10,14,17,23-24H,1-4H2,(H,20,26)(H2,16,18,19)(H2,21,25,27,28)/t6-,7+,9+,10+,14+/m0/s1

> <INCHI_KEY>
SEHSCEYJWJDMSC-XLZJSAHRSA-N

> <FORMULA>
C15H22N7O8P

> <MOLECULAR_WEIGHT>
459.356

> <EXACT_MASS>
459.126747694

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
42.60554813712288

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-8-oxo-8,9-dihydro-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2S)-pyrrolidin-2-yl]formamido})phosphinic acid

> <ALOGPS_LOGP>
-2.11

> <JCHEM_LOGP>
-3.9589485876019763

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.996301324113988

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.911784341735941

> <JCHEM_PKA_STRONGEST_BASIC>
9.758394784332147

> <JCHEM_POLAR_SURFACE_AREA>
221.48999999999998

> <JCHEM_REFRACTIVITY>
104.19679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-amino-8-oxo-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy((2S)-pyrrolidin-2-ylformamido)phosphinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 53 56  0  0  0  0  0  0  0  0999 V2000
   -8.2049    1.5228   -0.9192 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1791    0.5563   -0.7781 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2664   -0.7236   -1.1743 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2967   -1.6236   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927   -1.2646   -0.3209 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0401   -0.0066    0.1058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0086    0.9326   -0.1023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5622    2.0513    0.4199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3436    1.8549    0.9609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6741    2.7337    1.5331 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0098    0.5407    0.7637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376   -0.0168    1.2897 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6941    0.5714    0.7966 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6585   -0.3262    1.2774 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6395    0.1357    0.6596 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5948    0.0309   -0.6896 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9049    0.6736   -1.4455 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.9357    0.2109   -2.9269 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6797    2.3753   -1.4299 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4732    0.2274   -0.8467 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4997    1.2224   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    2.4165   -0.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8480    0.8095   -0.2011 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4063   -0.2692   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4534   -0.9046   -0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1532   -0.5070    1.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203    0.4417    1.1546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -1.5897    0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5950   -2.7510    1.0455 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6421   -1.4790    1.2542 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5438   -2.0219    2.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7043    1.7324   -1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5019    2.1086   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607   -2.6470   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0903    2.9738    0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8002    0.2507    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014   -0.3517    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.1924    0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490   -0.4718    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569    2.8152   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267   -0.7518   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5549    1.7301   -0.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5782   -0.9433   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8520    0.2049   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.0242   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344   -0.4647   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9848    0.0120    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525   -1.4270    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551   -0.1511    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -1.4943   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -3.2376    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -2.1164    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650   -2.7629    2.5824 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
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 17 16  1  1
 17 18  2  0
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 14 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
  7  2  1  0
 30 12  1  0
 11  6  1  0
 27 23  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  8 35  1  0
 12 36  1  1
 14 37  1  1
 15 38  1  0
 15 39  1  0
 19 40  1  0
 20 41  1  0
 23 42  1  1
 24 43  1  0
 24 44  1  0
 25 45  1  0
 25 46  1  0
 26 47  1  0
 26 48  1  0
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  N   UNK     0      -8.205   1.523  -0.919  0.00  0.00           N+0
HETATM    2  C   UNK     0      -7.179   0.556  -0.778  0.00  0.00           C+0
HETATM    3  N   UNK     0      -7.266  -0.724  -1.174  0.00  0.00           N+0
HETATM    4  C   UNK     0      -6.297  -1.624  -0.955  0.00  0.00           C+0
HETATM    5  N   UNK     0      -5.193  -1.265  -0.321  0.00  0.00           N+0
HETATM    6  C   UNK     0      -5.040  -0.007   0.106  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.009   0.933  -0.102  0.00  0.00           C+0
HETATM    8  N   UNK     0      -5.562   2.051   0.420  0.00  0.00           N+0
HETATM    9  C   UNK     0      -4.344   1.855   0.961  0.00  0.00           C+0
HETATM   10  O   UNK     0      -3.674   2.734   1.533  0.00  0.00           O+0
HETATM   11  N   UNK     0      -4.010   0.541   0.764  0.00  0.00           N+0
HETATM   12  C   UNK     0      -2.838  -0.017   1.290  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.694   0.571   0.797  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.659  -0.326   1.277  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.640   0.136   0.660  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.595   0.031  -0.690  0.00  0.00           O+0
HETATM   17  P   UNK     0       1.905   0.674  -1.446  0.00  0.00           P+0
HETATM   18  O   UNK     0       1.936   0.211  -2.927  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.680   2.375  -1.430  0.00  0.00           O+0
HETATM   20  N   UNK     0       3.473   0.227  -0.847  0.00  0.00           N+0
HETATM   21  C   UNK     0       4.500   1.222  -0.616  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.195   2.417  -0.789  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.848   0.810  -0.201  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.406  -0.269  -1.070  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.453  -0.905  -0.227  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.153  -0.507   1.177  0.00  0.00           C+0
HETATM   27  N   UNK     0       6.020   0.442   1.155  0.00  0.00           N+0
HETATM   28  C   UNK     0      -1.225  -1.590   0.675  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.595  -2.751   1.046  0.00  0.00           O+0
HETATM   30  C   UNK     0      -2.642  -1.479   1.254  0.00  0.00           C+0
HETATM   31  O   UNK     0      -2.544  -2.022   2.562  0.00  0.00           O+0
HETATM   32  H   UNK     0      -8.704   1.732  -1.808  0.00  0.00           H+0
HETATM   33  H   UNK     0      -8.502   2.109  -0.058  0.00  0.00           H+0
HETATM   34  H   UNK     0      -6.461  -2.647  -1.347  0.00  0.00           H+0
HETATM   35  H   UNK     0      -6.090   2.974   0.425  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.800   0.251   2.416  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.701  -0.352   2.345  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.795   1.192   1.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.449  -0.472   1.133  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.257   2.815  -2.070  0.00  0.00           H+0
HETATM   41  H   UNK     0       3.727  -0.752  -0.555  0.00  0.00           H+0
HETATM   42  H   UNK     0       6.555   1.730  -0.387  0.00  0.00           H+0
HETATM   43  H   UNK     0       5.578  -0.943  -1.376  0.00  0.00           H+0
HETATM   44  H   UNK     0       6.852   0.205  -1.993  0.00  0.00           H+0
HETATM   45  H   UNK     0       7.498  -2.024  -0.353  0.00  0.00           H+0
HETATM   46  H   UNK     0       8.434  -0.465  -0.541  0.00  0.00           H+0
HETATM   47  H   UNK     0       7.985   0.012   1.656  0.00  0.00           H+0
HETATM   48  H   UNK     0       6.853  -1.427   1.731  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.155  -0.151   1.422  0.00  0.00           H+0
HETATM   50  H   UNK     0      -1.295  -1.494  -0.457  0.00  0.00           H+0
HETATM   51  H   UNK     0      -0.219  -3.238   0.240  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.329  -2.116   0.744  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.865  -2.763   2.582  0.00  0.00           H+0
CONECT    1    2   32   33                                                  
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   34                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8    2                                                  
CONECT    8    7    9   35                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12    6                                                  
CONECT   12   11   13   30   36                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   28   37                                             
CONECT   15   14   16   38   39                                             
CONECT   16   15   17                                                       
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17   40                                                       
CONECT   20   17   21   41                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   27   42                                             
CONECT   24   23   25   43   44                                             
CONECT   25   24   26   45   46                                             
CONECT   26   25   27   47   48                                             
CONECT   27   26   23   49                                                  
CONECT   28   14   29   30   50                                             
CONECT   29   28   51                                                       
CONECT   30   28   31   12   52                                             
CONECT   31   30   53                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    4                                                            
CONECT   35    8                                                            
CONECT   36   12                                                            
CONECT   37   14                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   19                                                            
CONECT   41   20                                                            
CONECT   42   23                                                            
CONECT   43   24                                                            
CONECT   44   24                                                            
CONECT   45   25                                                            
CONECT   46   25                                                            
CONECT   47   26                                                            
CONECT   48   26                                                            
CONECT   49   27                                                            
CONECT   50   28                                                            
CONECT   51   29                                                            
CONECT   52   30                                                            
CONECT   53   31                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  112    0
END

RDKit          3D

53 56  0  0  0  0  0  0  0  0999 V2000
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    4.4997    1.2224   -0.6161 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1954    2.4165   -0.7889 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4063   -0.2692   -1.0701 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4534   -0.9046   -0.2268 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1532   -0.5070    1.1770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0203    0.4417    1.1546 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2254   -1.5897    0.6753 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.5438   -2.0219    2.5617 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.5019    2.1086   -0.0579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4607   -2.6470   -1.3468 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8002    0.2507    2.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7014   -0.3517    2.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7952    1.1924    0.9996 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4490   -0.4718    1.1330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569    2.8152   -2.0697 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7267   -0.7518   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5782   -0.9433   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8520    0.2049   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4982   -2.0242   -0.3533 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344   -0.4647   -0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9848    0.0120    1.6555 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8525   -1.4270    1.7312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1551   -0.1511    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2951   -1.4943   -0.4565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2189   -3.2376    0.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294   -2.1164    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650   -2.7629    2.5824 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
  9 10  2  0
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 14 28  1  0
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  7  2  1  0
 30 12  1  0
 11  6  1  0
 27 23  1  0
  1 32  1  0
  1 33  1  0
  4 34  1  0
  8 35  1  0
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 26 48  1  0
 27 49  1  0
 28 50  1  6
 29 51  1  0
 30 52  1  6
 31 53  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2S)-N-({[(2R,3S,4R,5R)-5-(6-amino-8-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)pyrrolidine-2-carboximidate	Generator

Chemical Formula

C₁₅H₂₂N₇O₈P

Average Mass

459.3560 Da

Monoisotopic Mass

459.12675 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-8-oxo-8,9-dihydro-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2S)-pyrrolidin-2-yl]formamido})phosphinic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-amino-8-oxo-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy((2S)-pyrrolidin-2-ylformamido)phosphinic acid

CAS Registry Number

Not Available

SMILES

NC1=C2NC(=O)N([C@@H]3O[C@H](COP(O)(=O)NC(=O)[C@@H]4CCCN4)[C@@H](O)[C@H]3O)C2=NC=N1

InChI Identifier

InChI=1S/C15H22N7O8P/c16-11-8-12(19-5-18-11)22(15(26)20-8)14-10(24)9(23)7(30-14)4-29-31(27,28)21-13(25)6-2-1-3-17-6/h5-7,9-10,14,17,23-24H,1-4H2,(H,20,26)(H2,16,18,19)(H2,21,25,27,28)/t6-,7+,9+,10+,14+/m0/s1

InChI Key

SEHSCEYJWJDMSC-XLZJSAHRSA-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
Streptomyces	NPAtlas	8641999

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. strain RK-16	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	-2.1	ALOGPS
logP	-4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	-3.9	ChemAxon
pKa (Strongest Basic)	9.76	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	221.49 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	104.2 m³·mol⁻¹	ChemAxon
Polarizability	42.61 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

NPAtlas ID

NPA016235

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8131444

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9955834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Matsuura N, Onose R, Osada H: Morphology reversion activity of phosmidosine and phosmidosine B, a newly isolated derivative, on src transformed NRK cells. J Antibiot (Tokyo). 1996 Apr;49(4):361-5. doi: 10.7164/antibiotics.49.361. [PubMed:8641999 ]
Moriguchi T, Asai N, Okada K, Seio K, Sasaki T, Sekine M: First synthesis and anticancer activity of phosmidosine and its related compounds. J Org Chem. 2002 May 17;67(10):3290-300. doi: 10.1021/jo016176g. [PubMed:12003538 ]

Showing NP-Card for Phosmidosine B (NP0023147)

MOL for NP0023147 (Phosmidosine B)

3D MOL for NP0023147 (Phosmidosine B)

3D SDF for NP0023147 (Phosmidosine B)

3D-SDF for NP0023147 (Phosmidosine B)

PDB for NP0023147 (Phosmidosine B)

3D PDB for NP0023147 (Phosmidosine B)

SMILES for NP0023147 (Phosmidosine B)

INCHI for NP0023147 (Phosmidosine B)

Structure for NP0023147 (Phosmidosine B)

3D Structure for NP0023147 (Phosmidosine B)