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Human Metabolome Database Version 3.5

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Showing metabocard for S-(PGJ2)-glutathione (HMDB13063)

Record Information
Version 3.5
Creation Date 2009-07-24 18:12:34 -0600
Update Date 2013-02-08 17:29:44 -0700
HMDB ID HMDB13063
Secondary Accession Numbers None
Metabolite Identification
Common Name S-(PGJ2)-glutathione
Description 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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 9-(S-Glutathionyl)-prostaglandin J(,2)
  2. GSPGJ2
Chemical Formula C30H47N3O10S
Average Molecular Weight 641.773
Monoisotopic Molecular Weight 641.298215429
IUPAC Name (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
Traditional IUPAC Name (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
CAS Registry Number Not Available
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
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/h4,7,12-13,19-23,25,34H,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
InChI Key RJCPXHXLCWWGHO-APFRPCTBSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Amino Acids, Peptides, and Analogues
Class Peptides
Sub Class N/A
Other Descriptors
  • Aliphatic Homomonocyclic Compounds
  • Carbocyclic Fatty Acids
  • Keto Fatty Acids
  • Organic Compounds
  • Thia Fatty Acids
  • Unsaturated Fatty Acids
Substituents
  • Allyl Alcohol
  • Alpha Amino Acid Or Derivative
  • Carboxamide Group
  • Carboxylic Acid Salt
  • Ketone
  • N Acyl Alpha Amino Acid
  • N Acylglycine
  • Primary Aliphatic Amine (Alkylamine)
  • Prostaglandin Skeleton
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thioether
  • Tricarboxylic Acid Derivative
Direct Parent Peptides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
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
Water Solubility 0.011 g/L ALOGPS
LogP -1.19 ALOGPS
LogP -0.98 ChemAxon
LogS -4.77 ALOGPS
pKa (strongest acidic) 1.81 ChemAxon
pKa (strongest basic) 9.31 ChemAxon
Hydrogen Acceptor Count 11 ChemAxon
Hydrogen Donor Count 7 ChemAxon
Polar Surface Area 233.42 A2 ChemAxon
Rotatable Bond Count 23 ChemAxon
Refractivity 165.04 ChemAxon
Polarizability 67.64 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029278
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
NuGOwiki Link HMDB13063 Link_out
Metagene Link HMDB13063 Link_out
METLIN ID Not Available
PubChem Compound 53481603 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Glutathione S-transferase theta-2
Reactions:
  • RX + glutathione = HX + R-S-glutathione [RN:R03522 R08511 R08512]
Gene Name: GSTT2
Uniprot ID: P0CG29 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA