Record Information
Version3.6
Creation Date2009-07-25 00:12:34 UTC
Update Date2013-02-09 00:29:44 UTC
HMDB IDHMDB13063
Secondary Accession NumbersNone
Metabolite Identification
Common NameS-(PGJ2)-glutathione
DescriptionS-(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
Synonyms
  1. 9-(S-Glutathionyl)-prostaglandin J(,2)
  2. GSPGJ2
Chemical FormulaC30H47N3O10S
Average Molecular Weight641.773
Monoisotopic Molecular Weight641.298215429
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 NumberNot 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 KeyRJCPXHXLCWWGHO-APFRPCTBSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAmino Acids, Peptides, and Analogues
ClassPeptides
Sub ClassN/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 ParentPeptides
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility0.011 g/LALOGPS
logP-1.2ALOGPS
logP-0.98ChemAxon
logS-4.8ALOGPS
pKa (strongest acidic)1.81ChemAxon
pKa (strongest basic)9.31ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count7ChemAxon
polar surface area233.42ChemAxon
rotatable bond count23ChemAxon
refractivity165.04ChemAxon
polarizability67.64ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB029278
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB13063
Metagene LinkHMDB13063
METLIN IDNot Available
PubChem Compound53481603
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
GSTT2
Uniprot ID:
P0CG29