NP-MRD: Showing NP-Card for Phosmidosine (NP0061607)

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Record Information

Version

2.0

Created at

2022-04-28 06:22:01 UTC

Updated at

2022-04-28 06:22:01 UTC

NP-MRD ID

NP0061607

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phosmidosine

Description

(2R)-N-[(R)-{[(2R,3R,4S,5R)-5-(6-amino-8-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(methoxy)phosphoryl]pyrrolidine-2-carboximidic acid belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether). Phosmidosine is found in Streptomyces sp. RK-16. Based on a literature review very few articles have been published on (2R)-N-[(R)-{[(2R,3R,4S,5R)-5-(6-amino-8-hydroxy-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(methoxy)phosphoryl]pyrrolidine-2-carboximidic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208222D          

 32 35  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    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   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468   -5.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263   -5.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -6.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592   -6.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -6.8106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6804   -7.6356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650   -7.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9499   -7.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650   -6.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  3  7  1  0  0  0  0
  2  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
  1 11  1  0  0  0  0
 12 11  1  1  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
 12 16  1  0  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 14 31  1  1  0  0  0
 13 32  1  1  0  0  0
M  END

     RDKit          3D

 56 59  0  0  0  0  0  0  0  0999 V2000
    2.5725   -0.6174   -3.2229 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3883    0.7478   -3.3190 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4142    1.4072   -1.7746 P   0  0  2  0  0  5  0  0  0  0  0  0
    1.9359    2.8422   -1.7559 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0689    1.3944   -1.1920 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5141    0.2312   -0.5096 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7791   -0.7682   -0.3127 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250    0.1643    0.0124 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.1801    1.2510    1.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3454    0.6406    1.8172 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3351   -0.8270    1.5023 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1807   -1.0841    0.6676 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3956    0.5186   -0.7813 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1135    1.0498   -0.9022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8674    0.3024   -0.0358 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1531    0.8056   -0.1318 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8829   -0.1408    0.6195 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.3005   -0.0340    0.3768 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9121    0.0926   -0.8134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3519    0.1401   -1.9247 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2565    0.1634   -0.6339 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5116    0.0818    0.6799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6839    0.1014    1.4051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9610    0.2258    0.8048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5987   -0.0032    2.7420 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4092   -0.1243    3.3715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2943   -0.1401    2.6433 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2651   -0.0423    1.3010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3348   -1.4912    0.2452 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2139   -2.2389   -0.5287 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0773   -1.1248   -0.5312 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3464   -1.1633   -1.8846 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2909   -1.1299   -4.1689 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0144   -1.0910   -2.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6592   -0.8447   -3.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125    2.1823   -1.3249 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6331    0.2732   -0.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2923    1.4058    1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4894    2.1639    0.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1528    0.8677    2.8861 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2761    1.1230    1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2339   -1.4244    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2266   -1.1359    0.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3348   -1.8137   -0.0460 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1025    2.1067   -0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1440    1.0405   -1.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500    0.2375    1.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6257    0.0675    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9739    0.2635   -1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0881   -0.0537   -0.1777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7664    0.5978    1.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3936   -0.2048    4.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9882   -2.0650    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7570   -2.8581   -0.0013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2197   -1.7532   -0.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6395   -0.3157   -2.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  6
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  3 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 12  8  1  0
 31 15  1  0
 28 18  1  0
 28 22  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  5 36  1  0
  8 37  1  6
  9 38  1  0
  9 39  1  0
 10 40  1  0
 10 41  1  0
 11 42  1  0
 11 43  1  0
 12 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  1
 17 48  1  1
 29 53  1  1
 30 54  1  0
 31 55  1  6
 32 56  1  0
 21 49  1  0
 24 50  1  0
 24 51  1  0
 26 52  1  0
M  END


  Mrv1652304282208222D          

 32 35  0  0  1  0            999 V2000
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    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   -1.5229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.9521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984   -2.1500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0865   -2.8174    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3984   -3.4849    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -3.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1831   -2.4049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -3.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7643   -4.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4317   -5.0203    0.0000 P   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9166   -4.3528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9468   -5.6877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263   -5.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0991   -5.5052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0129   -6.3257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2592   -6.6612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6804   -6.8106    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6804   -7.6356    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650   -7.8905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9499   -7.2231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4650   -6.5557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -4.2695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9115   -2.8174    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
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  2  0  0  0  0
  3  7  1  0  0  0  0
  2  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
  1 11  1  0  0  0  0
 12 11  1  1  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
 12 16  1  0  0  0  0
 15 17  1  1  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 26 24  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  1  0  0  0  0
 14 31  1  1  0  0  0
 13 32  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0061607

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[P@](=O)(NC(=O)[C@H]1CCCN1)OC[C@H]1O[C@H]([C@@H](O)[C@H]1O)N1C(=O)NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C16H24N7O8P/c1-29-32(28,22-14(26)7-3-2-4-18-7)30-5-8-10(24)11(25)15(31-8)23-13-9(21-16(23)27)12(17)19-6-20-13/h6-8,10-11,15,18,24-25H,2-5H2,1H3,(H,21,27)(H2,17,19,20)(H,22,26,28)/t7-,8-,10+,11+,15-,32-/m1/s1

> <INCHI_KEY>
HBJDRXMCLFRSGN-DGYZGGPXSA-N

> <FORMULA>
C16H24N7O8P

> <MOLECULAR_WEIGHT>
473.383

> <EXACT_MASS>
473.142397759

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
43.12784454807405

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-N-[(R)-{[(2R,3R,4S,5R)-5-(6-amino-8-oxo-8,9-dihydro-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(methoxy)phosphoryl]pyrrolidine-2-carboxamide

> <ALOGPS_LOGP>
-2.10

> <JCHEM_LOGP>
-3.4468092635952683

> <ALOGPS_LOGS>
-1.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.530599615427

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.490183813121872

> <JCHEM_PKA_STRONGEST_BASIC>
9.958941223076433

> <JCHEM_POLAR_SURFACE_AREA>
210.48999999999998

> <JCHEM_REFRACTIVITY>
108.67909999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-N-[(R)-[(2R,3R,4S,5R)-5-(6-amino-8-oxo-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(methoxy)phosphoryl]pyrrolidine-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       3.864  -0.533   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       2.530  -2.843   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0       2.530   1.777   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -0.268  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.713  -1.303   0.000  0.00  0.00           O+0
HETATM   11  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.744  -4.013   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.161  -5.259   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.744  -6.505   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.208  -6.029   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.208  -4.489   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.454  -6.934   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.293  -8.466   0.000  0.00  0.00           O+0
HETATM   19  P   UNK     0      -4.539  -9.371   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      -5.444  -8.125   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -3.634 -10.617   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.102 -10.456   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      -5.785 -10.276   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0      -5.624 -11.808   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -4.217 -12.434   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.870 -12.713   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -6.870 -14.253   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -8.335 -14.729   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.240 -13.483   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.335 -12.237   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.268  -7.970   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.701  -5.259   0.000  0.00  0.00           O+0
CONECT    1    2    6   11                                                  
CONECT    2    1    3    8                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3                                                            
CONECT    8    2    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    1   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14   32                                                  
CONECT   14   13   15   31                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15   12                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   23                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23   19   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
CONECT   31   14                                                            
CONECT   32   13                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₁₆H₂₄N₇O₈P

Average Mass

473.3830 Da

Monoisotopic Mass

473.14240 Da

IUPAC Name

(2R)-N-[(R)-{[(2R,3R,4S,5R)-5-(6-amino-8-oxo-8,9-dihydro-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(methoxy)phosphoryl]pyrrolidine-2-carboxamide

Traditional Name

(2R)-N-[(R)-[(2R,3R,4S,5R)-5-(6-amino-8-oxo-7H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(methoxy)phosphoryl]pyrrolidine-2-carboxamide

CAS Registry Number

Not Available

SMILES

CO[P@](=O)(NC(=O)[C@H]1CCCN1)OC[C@H]1O[C@H]([C@@H](O)[C@H]1O)N1C(=O)NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C16H24N7O8P/c1-29-32(28,22-14(26)7-3-2-4-18-7)30-5-8-10(24)11(25)15(31-8)23-13-9(21-16(23)27)12(17)19-6-20-13/h6-8,10-11,15,18,24-25H,2-5H2,1H3,(H,21,27)(H2,17,19,20)(H,22,26,28)/t7-,8-,10+,11+,15-,32-/m1/s1

InChI Key

HBJDRXMCLFRSGN-DGYZGGPXSA-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 sp. RK-16	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glycosylamines. Glycosylamines are compounds consisting of an amine with a beta-N-glycosidic bond to a carbohydrate, thus forming a cyclic hemiaminal ether bond (alpha-amino ether).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glycosylamines

Alternative Parents

Substituents

N-glycosyl compound
Pentose monosaccharide
6-aminopurine
Purine
Imidazopyrimidine
Aminopyrimidine
Imidolactam
Pyrimidine
Phosphoric acid ester
Organic phosphoric acid derivative
N-substituted imidazole
Monosaccharide
Heteroaromatic compound
Tetrahydrofuran
Pyrrolidine
Imidazole
Azole
Secondary alcohol
1,2-diol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organonitrogen compound
Amine
Alcohol
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	-2.1	ALOGPS
logP	-3.4	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	5.49	ChemAxon
pKa (Strongest Basic)	9.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	210.49 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	108.68 m³·mol⁻¹	ChemAxon
Polarizability	43.13 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

163061803

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Phosmidosine (NP0061607)

MOL for NP0061607 (Phosmidosine)

3D MOL for NP0061607 (Phosmidosine)

3D SDF for NP0061607 (Phosmidosine)

3D-SDF for NP0061607 (Phosmidosine)

PDB for NP0061607 (Phosmidosine)

3D PDB for NP0061607 (Phosmidosine)

SMILES for NP0061607 (Phosmidosine)

INCHI for NP0061607 (Phosmidosine)

Structure for NP0061607 (Phosmidosine)

3D Structure for NP0061607 (Phosmidosine)