NP-MRD: Showing NP-Card for Sulphostin (NP0003941)

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Record Information

Version

1.0

Created at

2020-12-09 01:28:48 UTC

Updated at

2021-07-15 16:47:48 UTC

NP-MRD ID

NP0003941

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Sulphostin

Provided By

NPAtlas

Description

(3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. Sulphostin is found in Streptomyces. It was first documented in 2001 (PMID: 11714231). Based on a literature review very few articles have been published on (3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one (PMID: 31926305) (PMID: 15835723) (PMID: 15653346) (PMID: 15217282).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117513D          

 29 29  0  0  0  0            999 V2000
   -2.9803    1.6638   -1.6113 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6212    0.8596   -0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6050   -0.5950   -0.9483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2506   -1.5439    0.1787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0105   -1.0513    0.8844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3690    0.0618    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    0.0058   -0.1330 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.6438   -1.5568   -0.8999 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.7610    1.0586   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    0.1476    1.3563 N   0  0  2  0  0  0  0  0  0  0  0  0
    3.9126    0.4597    1.0127 S   0  0  2  0  0  6  0  0  0  0  0  0
    4.3393   -0.1952   -0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -0.1372    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    2.1044    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.1684   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.3020   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    2.0859   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508    2.3407   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761    1.0109    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173   -0.8699   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.6435   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.5176   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -1.6470    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -0.6947    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.8798    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564   -1.4745   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -2.2325   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.7786    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    2.5482    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  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  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 14 29  1  0  0  0  0
M  END

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.9803    1.6638   -1.6113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    0.8596   -0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6050   -0.5950   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -1.5439    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105   -1.0513    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    0.0618    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    0.0058   -0.1330 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.6438   -1.5568   -0.8999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    1.0586   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    0.1476    1.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126    0.4597    1.0127 S   0  0  2  0  0  6  0  0  0  0  0  0
    4.3393   -0.1952   -0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -0.1372    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    2.1044    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.1684   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.3020   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    2.0859   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508    2.3407   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761    1.0109    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173   -0.8699   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.6435   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.5176   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -1.6470    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -0.6947    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.8798    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564   -1.4745   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -2.2325   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.7786    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    2.5482    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  6
  6 15  1  0
 15 16  2  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 14 29  1  0
M  END


  Mrv1652306242117513D          

 29 29  0  0  0  0            999 V2000
   -2.9803    1.6638   -1.6113 N   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6212    0.8596   -0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6050   -0.5950   -0.9483 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2506   -1.5439    0.1787 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0105   -1.0513    0.8844 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3690    0.0618    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    0.0058   -0.1330 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.6438   -1.5568   -0.8999 N   0  0  1  0  0  0  0  0  0  0  0  0
    1.7610    1.0586   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    0.1476    1.3563 N   0  0  2  0  0  0  0  0  0  0  0  0
    3.9126    0.4597    1.0127 S   0  0  2  0  0  6  0  0  0  0  0  0
    4.3393   -0.1952   -0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -0.1372    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    2.1044    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.1684   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.3020   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    2.0859   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508    2.3407   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761    1.0109    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173   -0.8699   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.6435   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.5176   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -1.6470    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -0.6947    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.8798    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564   -1.4745   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -2.2325   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.7786    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    2.5482    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  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  2  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  2  0  0  0  0
 11 14  1  6  0  0  0
  6 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15  2  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  2 19  1  1  0  0  0
  3 20  1  0  0  0  0
  3 21  1  0  0  0  0
  4 22  1  0  0  0  0
  4 23  1  0  0  0  0
  5 24  1  0  0  0  0
  5 25  1  0  0  0  0
  8 26  1  0  0  0  0
  8 27  1  0  0  0  0
 10 28  1  0  0  0  0
 14 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003941

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[S](=O)(=O)N([H])[P@@](=O)(N([H])[H])N1C(=O)[C@@]([H])(N([H])[H])C([H])([H])C([H])([H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C5H13N4O5PS/c6-4-2-1-3-9(5(4)10)15(7,11)8-16(12,13)14/h4H,1-3,6H2,(H3,7,8,11)(H,12,13,14)/t4-,15-/m0/s1

> <INCHI_KEY>
AYVBXTCIPLYEBG-NMAPHRJESA-N

> <FORMULA>
C5H13N4O5PS

> <MOLECULAR_WEIGHT>
272.22

> <EXACT_MASS>
272.034427707

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
22.790371628489453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one

> <ALOGPS_LOGP>
-1.47

> <JCHEM_LOGP>
-4.245955246144266

> <ALOGPS_LOGS>
-1.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.174533032752305

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.0286687433366621

> <JCHEM_PKA_STRONGEST_BASIC>
7.963817844477963

> <JCHEM_POLAR_SURFACE_AREA>
155.81999999999996

> <JCHEM_REFRACTIVITY>
54.77290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
   -2.9803    1.6638   -1.6113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    0.8596   -0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6050   -0.5950   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -1.5439    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105   -1.0513    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    0.0618    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    0.0058   -0.1330 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.6438   -1.5568   -0.8999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    1.0586   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    0.1476    1.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126    0.4597    1.0127 S   0  0  2  0  0  6  0  0  0  0  0  0
    4.3393   -0.1952   -0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -0.1372    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    2.1044    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.1684   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.3020   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    2.0859   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508    2.3407   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761    1.0109    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173   -0.8699   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.6435   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.5176   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -1.6470    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -0.6947    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.8798    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564   -1.4745   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -2.2325   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.7786    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    2.5482    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  6
  6 15  1  0
 15 16  2  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 14 29  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      -2.980   1.664  -1.611  0.00  0.00           N+0
HETATM    2  C   UNK     0      -2.621   0.860  -0.460  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.605  -0.595  -0.948  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.251  -1.544   0.179  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.010  -1.051   0.884  0.00  0.00           C+0
HETATM    6  N   UNK     0      -0.369   0.062   0.210  0.00  0.00           N+0
HETATM    7  P   UNK     0       1.343   0.006  -0.133  0.00  0.00           P+0
HETATM    8  N   UNK     0       1.644  -1.557  -0.900  0.00  0.00           N+0
HETATM    9  O   UNK     0       1.761   1.059  -1.127  0.00  0.00           O+0
HETATM   10  N   UNK     0       2.246   0.148   1.356  0.00  0.00           N+0
HETATM   11  S   UNK     0       3.913   0.460   1.013  0.00  0.00           S+0
HETATM   12  O   UNK     0       4.339  -0.195  -0.278  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.755  -0.137   2.102  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.241   2.104   0.910  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.192   1.168  -0.154  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.682   2.302  -0.195  0.00  0.00           O+0
HETATM   17  H   UNK     0      -3.909   2.086  -1.514  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.251   2.341  -1.893  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.276   1.011   0.396  0.00  0.00           H+0
HETATM   20  H   UNK     0      -3.517  -0.870  -1.465  0.00  0.00           H+0
HETATM   21  H   UNK     0      -1.723  -0.644  -1.655  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.996  -2.518  -0.288  0.00  0.00           H+0
HETATM   23  H   UNK     0      -3.103  -1.647   0.901  0.00  0.00           H+0
HETATM   24  H   UNK     0      -1.245  -0.695   1.933  0.00  0.00           H+0
HETATM   25  H   UNK     0      -0.269  -1.880   1.038  0.00  0.00           H+0
HETATM   26  H   UNK     0       2.256  -1.474  -1.744  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.058  -2.232  -0.205  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.159  -0.779   1.869  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.286   2.548   1.781  0.00  0.00           H+0
CONECT    1    2   17   18                                                  
CONECT    2    1    3   15   19                                             
CONECT    3    2    4   20   21                                             
CONECT    4    3    5   22   23                                             
CONECT    5    4    6   24   25                                             
CONECT    6    5    7   15                                                  
CONECT    7    6    8    9   10                                             
CONECT    8    7   26   27                                                  
CONECT    9    7                                                            
CONECT   10    7   11   28                                                  
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   29                                                       
CONECT   15    6   16    2                                                  
CONECT   16   15                                                            
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    2                                                            
CONECT   20    3                                                            
CONECT   21    3                                                            
CONECT   22    4                                                            
CONECT   23    4                                                            
CONECT   24    5                                                            
CONECT   25    5                                                            
CONECT   26    8                                                            
CONECT   27    8                                                            
CONECT   28   10                                                            
CONECT   29   14                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

RDKit          3D

29 29  0  0  0  0  0  0  0  0999 V2000
   -2.9803    1.6638   -1.6113 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6212    0.8596   -0.4597 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6050   -0.5950   -0.9483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -1.5439    0.1787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0105   -1.0513    0.8844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3690    0.0618    0.2095 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    0.0058   -0.1330 P   0  0  1  0  0  5  0  0  0  0  0  0
    1.6438   -1.5568   -0.8999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7610    1.0586   -1.1265 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2461    0.1476    1.3563 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9126    0.4597    1.0127 S   0  0  2  0  0  6  0  0  0  0  0  0
    4.3393   -0.1952   -0.2780 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -0.1372    2.1019 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2409    2.1044    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1925    1.1684   -0.1542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6824    2.3020   -0.1951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9092    2.0859   -1.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2508    2.3407   -1.8929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761    1.0109    0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173   -0.8699   -1.4652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228   -0.6435   -1.6550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9961   -2.5176   -0.2884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1035   -1.6470    0.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451   -0.6947    1.9332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2691   -1.8798    1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2564   -1.4745   -1.7443 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0577   -2.2325   -0.2049 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1591   -0.7786    1.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2863    2.5482    1.7814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  6
  7  9  2  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  6
  6 15  1  0
 15 16  2  0
 15  2  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  1
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 14 29  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(3S)-3-Amino-1-[(R)-amino(sulphoamino)phosphoryl]piperidin-2-one	Generator
Sulfostin	Generator

Chemical Formula

C₅H₁₃N₄O₅PS

Average Mass

272.2200 Da

Monoisotopic Mass

272.03443 Da

IUPAC Name

(3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one

Traditional Name

(3S)-3-amino-1-[(R)-amino(sulfoamino)phosphoryl]piperidin-2-one

CAS Registry Number

Not Available

SMILES

N[C@H]1CCCN(C1=O)[P@@](N)(=O)NS(O)(=O)=O

InChI Identifier

InChI=1S/C5H13N4O5PS/c6-4-2-1-3-9(5(4)10)15(7,11)8-16(12,13)14/h4H,1-3,6H2,(H3,7,8,11)(H,12,13,14)/t4-,15-/m0/s1

InChI Key

AYVBXTCIPLYEBG-NMAPHRJESA-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	11714231

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
3-aminopiperidine
Delta-lactam
Piperidinone
Organic phosphoric acid derivative
Organic phosphoric acid amide
Piperidine
Organic sulfuric acid or derivatives
Lactam
Azacycle
Organoheterocyclic compound
Organonitrogen compound
Organic nitrogen compound
Primary aliphatic amine
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Amine
Organooxygen compound
Primary amine
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	-1.5	ALOGPS
logP	-4.2	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	-1	ChemAxon
pKa (Strongest Basic)	7.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	155.82 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.77 m³·mol⁻¹	ChemAxon
Polarizability	22.79 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA008605

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7971236

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

Akiyama T, Abe M, Harada S, Kojima F, Sawa R, Takahashi Y, Naganawa H, Homma Y, Hamada M, Yamaguchi A, Aoyagi T, Muraoka Y, Takeuchi T: Sulphostin, a potent inhibitor for dipeptidyl peptidase IV from Streptomyces sp. MK251-43F3. J Antibiot (Tokyo). 2001 Sep;54(9):744-6. doi: 10.7164/antibiotics.54.744. [PubMed:11714231 ]
Femmer C, Bechtold M, Held M, Panke S: In vivo directed enzyme evolution in nanoliter reactors with antimetabolite selection. Metab Eng. 2020 May;59:15-23. doi: 10.1016/j.ymben.2020.01.003. Epub 2020 Jan 8. [PubMed:31926305 ]
Abe M, Abe F, Nishimura C, Ichimura E, Ogasawara A, Ichinei M, Muraoka Y, Saino T: Sulphostin, a novel inhibitor of dipeptidyl peptidases IV (DPPIV) that stimulates hematopoiesis in mice. J Antibiot (Tokyo). 2005 Feb;58(2):111-7. doi: 10.1038/ja.2005.14. [PubMed:15835723 ]
Abe M, Akiyama T, Umezawa Y, Yamamoto K, Nagai M, Yamazaki H, Ichikawa Y, Muraoka Y: Synthesis and biological activity of sulphostin analogues, novel dipeptidyl peptidase IV inhibitors. Bioorg Med Chem. 2005 Feb 1;13(3):785-97. doi: 10.1016/j.bmc.2004.10.036. [PubMed:15653346 ]
Abe M, Akiyama T, Nakamura H, Kojima F, Harada S, Muraoka Y: First synthesis and determination of the absolute configuration of sulphostin, a novel inhibitor of dipeptidyl peptidase IV. J Nat Prod. 2004 Jun;67(6):999-1004. doi: 10.1021/np030491b. [PubMed:15217282 ]

Showing NP-Card for Sulphostin (NP0003941)

MOL for NP0003941 (Sulphostin)

3D MOL for NP0003941 (Sulphostin)

3D SDF for NP0003941 (Sulphostin)

3D-SDF for NP0003941 (Sulphostin)

PDB for NP0003941 (Sulphostin)

3D PDB for NP0003941 (Sulphostin)

SMILES for NP0003941 (Sulphostin)

INCHI for NP0003941 (Sulphostin)

Structure for NP0003941 (Sulphostin)

3D Structure for NP0003941 (Sulphostin)