1.0 2011-09-21 01:53:02 UTC 2015-07-21 06:59:40 UTC FDB029278 S-(PGJ2)-glutathione S-(PGJ2)-glutathione is a glutathione conjugate of prostaglandin J2. By reacting with glutathione and proteins, 15-d-PGJ(2) is believed to exert potent biological activity. HepG2 cells primarily convert 15-d-PGJ(2) to a glutathione conjugate in which the carbonyl at C-11 is reduced to a hydroxyl. Subsequently, the glutathione portion of the molecule is hydrolyzed with loss of glutamic acid and glycine resulting in a cysteine conjugate. These findings confirm a general route for the metabolism of cyclopentenone eicosanoids in HepG2 cells and may pave the way for new insights regarding the formation of 15-d-PGJ(2) in vivo. [HMDB] 9-(S-glutathionyl)-prostaglandin J(,2) GSPGJ2 C30H47N3O10S 641.773 641.298215429 (5Z)-7-[(1R,2R)-5-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid (5Z)-7-[(1R,2R)-5-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid CCCCC[C@H](O)\C=C\[C@@H]1[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=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/h4,7,12-13,19-23,25,34H,2-3,5-6,8-11,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,13-12+/t19-,20+,21+,22+,23+,25?/m0/s1 RJCPXHXLCWWGHO-APFRPCTBSA-N 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. Oligopeptides Organic compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Aliphatic homomonocyclic compounds Alpha amino acid amides Amino acids Carboxylic acids Cyclic ketones Cysteine and derivatives D-alpha-amino acids Dialkylthioethers Gamma-glutamyl peptides Glutamine and derivatives Hydrocarbon derivatives Monoalkylamines N-acyl amines N-acyl-alpha amino acids Organic oxides Organopnictogen compounds Prostaglandins and related compounds Secondary alcohols Secondary carboxylic acid amides Sulfenyl compounds Tricarboxylic acids and derivatives Alcohol Aliphatic homomonocyclic compound Alpha-amino acid Alpha-amino acid amide Alpha-amino acid or derivatives Alpha-oligopeptide Amine Amino acid Amino acid or derivatives Carbonyl group Carboxamide group Carboxylic acid Cyclic ketone Cysteine or derivatives D-alpha-amino acid Dialkylthioether Eicosanoid Fatty acyl Fatty amide Gamma-glutamyl alpha peptide Glutamine or derivatives Hydrocarbon derivative Ketone N-acyl-alpha amino acid or derivatives N-acyl-alpha-amino acid N-acyl-amine N-substituted-alpha-amino acid Organic nitrogen compound Organic oxide Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Organosulfur compound Primary aliphatic amine Primary amine Prostaglandin skeleton Secondary alcohol Secondary carboxylic acid amide Sulfenyl compound Thioether Tricarboxylic acid or derivatives Solid logp -1.19 ALOGPS logs -4.77 ALOGPS solubility 1.08e-02 g/l ALOGPS logp -0.98 ChemAxon pka_strongest_acidic 1.81 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (5Z)-7-[(1R,2R)-5-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid ChemAxon average_mass 641.773 ChemAxon mono_mass 641.298215429 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@@H]1[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 ChemAxon formula C30H47N3O10S ChemAxon inchi 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/h4,7,12-13,19-23,25,34H,2-3,5-6,8-11,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,13-12+/t19-,20+,21+,22+,23+,25?/m0/s1 ChemAxon inchikey RJCPXHXLCWWGHO-APFRPCTBSA-N ChemAxon polar_surface_area 233.42 ChemAxon refractivity 165.04 ChemAxon polarizability 67.64 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 300526 Specdb::MsMs 300527 Specdb::MsMs 300528 Specdb::MsMs 342802 Specdb::MsMs 342803 Specdb::MsMs 342804 Specdb::MsMs 2326803 Specdb::MsMs 2326804 Specdb::MsMs 2326805 Specdb::MsMs 2611828 Specdb::MsMs 2611829 Specdb::MsMs 2611830 Specdb::NmrOneD 152070 Specdb::NmrOneD 152071 Specdb::NmrOneD 152072 Specdb::NmrOneD 152073 Specdb::NmrOneD 152074 Specdb::NmrOneD 152075 Specdb::NmrOneD 152076 Specdb::NmrOneD 152077 Specdb::NmrOneD 152078 Specdb::NmrOneD 152079 Specdb::NmrOneD 152080 Specdb::NmrOneD 152081 Specdb::NmrOneD 152082 Specdb::NmrOneD 152083 Specdb::NmrOneD 152084 Specdb::NmrOneD 152085 Specdb::NmrOneD 152086 Specdb::NmrOneD 152087 Specdb::NmrOneD 152088 Specdb::NmrOneD 152089 Specdb::CMs 15580 Specdb::CMs 618244 Specdb::CMs 618245 Specdb::CMs 618246 Specdb::CMs 618247 Specdb::CMs 618248 Specdb::CMs 618249 Specdb::CMs 618250 Specdb::CMs 618251 Specdb::CMs 618252 Specdb::CMs 618253 Specdb::CMs 618254 Specdb::CMs 618255 Specdb::CMs 618256 Specdb::CMs 618257 Specdb::CMs 618258 Specdb::CMs 618259 Specdb::CMs 618260 Specdb::CMs 618261 Specdb::CMs 618262 Specdb::CMs 618263 Specdb::CMs 618264 Specdb::CMs 618265 Specdb::CMs 618266 Specdb::CMs 618267 HMDB13063 Glutathione S-transferase theta-2 P0CG29 GSTT2