1.0 2011-09-21 01:52:59 UTC 2015-07-21 06:59:40 UTC FDB029275 S-(9-Hydroxy-PGA2)-glutathione S-(9-hydroxy-PGA2)-glutathione is the glutathione conjugate of S-(9-hydroxy-PGA2) Inside L1210 cells, PGA2 was initially conjugated to glutathione and then reduced at the 9-keto position to form 9-OH-PGA2-GSH. The 9-OH-PGA2-GSH was then secreted from the cells and apparently degraded to form the CysGly and Cys derivatives. Intracellular glutathione was decreased markedly by the addition of the PGA2 in L1210 and L929 cells. This result confirms that conjugation of PGA2 to glutathione occurs in both cell types. Formation of the 9-OH-PGA2-GSH and other glutathione-related conjugates was prevented when glutathione was depleted by growth in buthionine sulfoximine. The glutathione-depleted cells were insensitive to the cytotoxicity of the PGA2, suggesting that one of the glutathione-related conjugates may be involved in the cytotoxicity of PGA2. These results end the controversy over the metabolism of PGA2 and suggest mechanisms for its antiviral and antigrowth actions [HMDB] 11-(S-glutathionyl)-9-hydroxyprostaglandin A(,2) GSOHPGA2 C30H49N3O10S 643.789 643.313865493 (5Z)-7-[(1R,2S)-3-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid (5Z)-7-[(1R,2S)-3-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-(carboxymethylcarbamoyl)ethyl]sulfanyl}-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid CCCCC[C@H](O)\C=C\[C@@H]1C(CC(O)[C@@H]1C\C=C/CCCC(O)=O)SC[C@@H](NC(=O)CC[C@@H](N)C(O)=O)C(=O)NCC(O)=O InChI=1S/C30H49N3O10S/c1-2-3-6-9-19(34)12-13-21-20(10-7-4-5-8-11-27(37)38)24(35)16-25(21)44-18-23(29(41)32-17-28(39)40)33-26(36)15-14-22(31)30(42)43/h4,7,12-13,19-25,34-35H,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+,24?,25?/m0/s1 KUKCWBNBPICNAJ-BTGAYFLPSA-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 -1.57 ALOGPS logs -4.62 ALOGPS solubility 1.55e-02 g/l ALOGPS logp -1.6 ChemAxon pka_strongest_acidic 1.81 ChemAxon pka_strongest_basic 9.31 ChemAxon iupac (5Z)-7-[(1R,2S)-3-{[(2S)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-5-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]hept-5-enoic acid ChemAxon average_mass 643.789 ChemAxon mono_mass 643.313865493 ChemAxon smiles CCCCC[C@H](O)\C=C\[C@@H]1C(CC(O)[C@@H]1C\C=C/CCCC(O)=O)SC[C@@H](NC(=O)CC[C@@H](N)C(O)=O)C(=O)NCC(O)=O ChemAxon formula C30H49N3O10S ChemAxon inchi InChI=1S/C30H49N3O10S/c1-2-3-6-9-19(34)12-13-21-20(10-7-4-5-8-11-27(37)38)24(35)16-25(21)44-18-23(29(41)32-17-28(39)40)33-26(36)15-14-22(31)30(42)43/h4,7,12-13,19-25,34-35H,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+,24?,25?/m0/s1 ChemAxon inchikey KUKCWBNBPICNAJ-BTGAYFLPSA-N ChemAxon polar_surface_area 236.58 ChemAxon refractivity 166.07 ChemAxon polarizability 69.43 ChemAxon rotatable_bond_count 23 ChemAxon acceptor_count 11 ChemAxon donor_count 8 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::NmrOneD 11742 Specdb::NmrOneD 11743 Specdb::NmrOneD 11744 Specdb::NmrOneD 11745 Specdb::NmrOneD 11746 Specdb::NmrOneD 11747 Specdb::NmrOneD 11748 Specdb::NmrOneD 11749 Specdb::NmrOneD 11750 Specdb::NmrOneD 11751 Specdb::NmrOneD 11752 Specdb::NmrOneD 11753 Specdb::NmrOneD 11754 Specdb::NmrOneD 11755 Specdb::NmrOneD 11756 Specdb::NmrOneD 11757 Specdb::NmrOneD 11758 Specdb::NmrOneD 11759 Specdb::NmrOneD 11760 Specdb::NmrOneD 11761 Specdb::CMs 20581 Specdb::CMs 625478 Specdb::CMs 625479 Specdb::CMs 625480 Specdb::CMs 625481 Specdb::CMs 625482 Specdb::CMs 625483 Specdb::CMs 625484 Specdb::CMs 625485 Specdb::CMs 625486 Specdb::CMs 625487 Specdb::CMs 625488 Specdb::CMs 625489 Specdb::CMs 625490 Specdb::CMs 625491 Specdb::CMs 625492 Specdb::CMs 625493 Specdb::CMs 625494 Specdb::CMs 625495 Specdb::CMs 625496 Specdb::CMs 625497 Specdb::CMs 625498 Specdb::CMs 625499 Specdb::CMs 625500 Specdb::CMs 625501 Specdb::MsMs 311839 Specdb::MsMs 311840 Specdb::MsMs 311841 Specdb::MsMs 356929 Specdb::MsMs 356930 Specdb::MsMs 356931 Specdb::MsMs 3059281 Specdb::MsMs 3059282 Specdb::MsMs 3059283 Specdb::MsMs 3107093 Specdb::MsMs 3107094 Specdb::MsMs 3107095 HMDB13060