NP-MRD: Showing NP-Card for S-(9-Deoxy-delta9,12-PGD2)-glutathione (NP0339171)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 20:04:09 UTC

Updated at

2024-09-11 20:04:10 UTC

NP-MRD ID

NP0339171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

S-(9-Deoxy-delta9,12-PGD2)-glutathione

Description

S-(9-deoxy-delta9,12-PGD2)-glutathione belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Identification of the GSH conjugate was accomplished by analysis by fast atom bombardment mass spectrometry following purification by high performance liquid chromatography. S-(9-deoxy-delta9,12-PGD2)-glutathione is a very strong basic compound (based on its pKa). Like other cytotoxic prostaglandins, this compound possesses an α,β-unsaturated ketone group to which cytotoxic activity has been attributed. This prostaglandin was found to readily conjugate with glutathione (GSH) in vitro. The major dehydration product of prostaglandin D2, 9-deoxy-d9,d12(E)-prostaglandin D2, is a potent cytotoxic compound. When 9-deoxy-d9,d12(E)-prostaglandin D2 was incubated with Chinese hamster ovary or hepatoma tissue culture cells, it was rapidly taken up and was recovered in the cell lysate primarily as a GSH conjugate in which the keto group at C-11 and the Δ12 double bond had been reduced.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016492D          

 44 44  0  0  1  0            999 V2000
   15.4713  -19.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263  -18.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1742  -18.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4291  -17.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8771  -16.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1321  -15.8380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9390  -15.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5800  -15.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8349  -14.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2829  -13.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4624  -13.9133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0499  -14.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -14.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -15.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -16.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -16.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -17.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -18.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9874  -18.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -18.9147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1269  -13.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7400  -12.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4544  -13.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2081  -12.6846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3199  -12.9882    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0650  -12.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2580  -12.0320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0031  -11.2474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1960  -11.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6440  -11.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411  -10.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4932   -9.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -8.8935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4313   -8.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7902   -8.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5972   -8.4519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5353   -7.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7059  -12.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8990  -12.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -13.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -14.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6638  -14.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1117  -15.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4708  -14.9990    0.0000 O   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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  1  6  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 38  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END


  Mrv1652303102016492D          

 44 44  0  0  1  0            999 V2000
   15.4713  -19.4181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7263  -18.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1742  -18.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4291  -17.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8771  -16.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1321  -15.8380    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.9390  -15.6665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5800  -15.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8349  -14.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2829  -13.8271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4624  -13.9133    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0499  -14.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -14.6278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -15.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -16.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -16.7713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -17.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8124  -18.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9874  -18.2002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2249  -18.9147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1269  -13.1597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7400  -12.6077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4544  -13.0202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2081  -12.6846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3199  -12.9882    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.0650  -12.2035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2580  -12.0320    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.0031  -11.2474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1960  -11.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6440  -11.6889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411  -10.2912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4932   -9.6781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2382   -8.8935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.4313   -8.7219    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.7902   -8.2804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5972   -8.4519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5353   -7.4958    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7059  -12.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8990  -12.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9609  -13.4298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4089  -14.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6638  -14.8274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1117  -15.4405    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4708  -14.9990    0.0000 O   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  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 23  1  0  0  0  0
 11 12  1  6  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 21 22  1  0  0  0  0
 21 25  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 38  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 38 39  2  0  0  0  0
 38 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)C\C=C1/[C@H](C\C=C/CCCC(O)=O)C(CC1=O)SC[C@H](NC(=O)CC[C@@H](N)C(O)=O)C(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H47N3O10S/c1-2-3-6-9-19(34)12-13-20-21(10-7-4-5-8-11-27(37)38)25(16-24(20)35)44-18-23(29(41)32-17-28(39)40)33-26(36)15-14-22(31)30(42)43/h4,7,13,19,21-23,25,34H,2-3,5-6,8-12,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,20-13+/t19-,21-,22+,23-,25?/m0/s1

> <INCHI_KEY>
RPHLHZIDWIFTII-RJQMMLODSA-N

> <FORMULA>
C30H47N3O10S

> <MOLECULAR_WEIGHT>
641.773

> <EXACT_MASS>
641.298215429

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
91

> <JCHEM_AVERAGE_POLARIZABILITY>
68.49230058360743

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z)-7-[(1S,2E)-5-{[(2R)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid

> <ALOGPS_LOGP>
-1.05

> <JCHEM_LOGP>
-0.9181141483651378

> <ALOGPS_LOGS>
-4.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
3.6339188661969435

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.807211554931743

> <JCHEM_PKA_STRONGEST_BASIC>
9.311520757216034

> <JCHEM_POLAR_SURFACE_AREA>
233.41999999999996

> <JCHEM_REFRACTIVITY>
164.95140000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z)-7-[(1S,2E)-5-{[(2R)-2-[(4R)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      28.880 -36.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.356 -34.782   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.325 -33.638   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      28.801 -32.173   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.771 -31.029   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.247 -29.564   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      29.753 -29.244   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      27.216 -28.420   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.692 -26.955   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.661 -25.811   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.130 -25.971   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.360 -27.305   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.820 -27.305   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.050 -28.639   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.820 -29.973   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.050 -31.306   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.820 -32.640   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      22.050 -33.974   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      20.510 -33.974   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      22.820 -35.307   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      24.504 -24.565   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.648 -23.534   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      26.982 -24.304   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      28.388 -23.678   0.000  0.00  0.00           O+0
HETATM   25  S   UNK     0      22.997 -24.245   0.000  0.00  0.00           S+0
HETATM   26  C   UNK     0      22.521 -22.780   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      21.015 -22.460   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      20.539 -20.995   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      19.033 -20.675   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      18.002 -21.819   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      18.557 -19.210   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      19.587 -18.066   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.111 -16.601   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      17.605 -16.281   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      20.142 -15.457   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      21.648 -15.777   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      19.666 -13.992   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      19.984 -23.604   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      18.478 -23.284   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      20.460 -25.069   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      19.430 -26.213   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      19.906 -27.678   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      18.875 -28.822   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      21.412 -27.998   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   23                                                  
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   11   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   10   22   24                                                  
CONECT   24   23                                                            
CONECT   25   21   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   38                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   27   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   88    0
END

View in JSmol

Synonyms

Value	Source
S-(9-Deoxy-δ9,12-PGD2)-glutathione	Generator
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid	Generator

Chemical Formula

C₃₀H₄₇N₃O₁₀S

Average Mass

641.7730 Da

Monoisotopic Mass

641.29822 Da

IUPAC Name

(5Z)-7-[(1S,2E)-5-{[(2R)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid

Traditional Name

(5Z)-7-[(1S,2E)-5-{[(2R)-2-[(4R)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)C\C=C1/[C@H](C\C=C/CCCC(O)=O)C(CC1=O)SC[C@H](NC(=O)CC[C@@H](N)C(O)=O)C(=O)NCC(O)=O

InChI Identifier

InChI=1S/C30H47N3O10S/c1-2-3-6-9-19(34)12-13-20-21(10-7-4-5-8-11-27(37)38)25(16-24(20)35)44-18-23(29(41)32-17-28(39)40)33-26(36)15-14-22(31)30(42)43/h4,7,13,19,21-23,25,34H,2-3,5-6,8-12,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,20-13+/t19-,21-,22+,23-,25?/m0/s1

InChI Key

RPHLHZIDWIFTII-RJQMMLODSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Oligopeptides

Alternative Parents

Substituents

Alpha-oligopeptide
Gamma-glutamyl alpha peptide
Prostaglandin skeleton
Eicosanoid
Glutamine or derivatives
N-acyl-alpha-amino acid
N-acyl-alpha amino acid or derivatives
Alpha-amino acid amide
Cysteine or derivatives
D-alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid
Alpha-amino acid or derivatives
Tricarboxylic acid or derivatives
Fatty amide
Fatty acyl
N-acyl-amine
Secondary alcohol
Secondary carboxylic acid amide
Cyclic ketone
Ketone
Carboxamide group
Amino acid or derivatives
Amino acid
Dialkylthioether
Carboxylic acid
Sulfenyl compound
Thioether
Primary amine
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Amine
Organic oxide
Organopnictogen compound
Organosulfur compound
Primary aliphatic amine
Organooxygen compound
Organonitrogen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	ALOGPS
logP	-0.92	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	1.81	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	233.42 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	164.95 m³·mol⁻¹	ChemAxon
Polarizability	68.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013058

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029273

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

53481598

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for S-(9-Deoxy-delta9,12-PGD2)-glutathione (NP0339171)

MOL for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

3D MOL for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

3D SDF for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

3D-SDF for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

PDB for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

3D PDB for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

SMILES for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

INCHI for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

Structure for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)

3D Structure for NP0339171 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)