ChemFOnt: Showing chemical card for S-(PGJ2)-glutathione (CFc000008190)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:51 UTC

Chemfont ID

CFc000008190

Molecule Identification

Common Name

S-(PGJ2)-glutathione

Definition

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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
9-(S-Glutathionyl)-prostaglandin J(,2)	HMDB
GSPGJ2	HMDB
(5Z)-7-[(1R,2R)-5-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1R,2R)-5-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1R,2R)-5-{[(2S)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-3-oxocyclopentyl]hept-5-enoic acid	Generator

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 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

None

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

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

Functional Ontology

Not Available

Endogenous (HMDB: HMDB0013063)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.98	ChemAxon
logS	-4.8	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	165.04 m³·mol⁻¹	ChemAxon
Polarizability	67.64 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

HMDB0013063

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029278

KNApSAcK ID

Not Available

Chemspider ID

35032572

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481603

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for S-(PGJ2)-glutathione (CFc000008190)

MOL for CFc000008190 (S-(PGJ2)-glutathione)

3D MOL for CFc000008190 (S-(PGJ2)-glutathione)

3D SDF for CFc000008190 (S-(PGJ2)-glutathione)

3D-SDF for CFc000008190 (S-(PGJ2)-glutathione)

PDB for CFc000008190 (S-(PGJ2)-glutathione)

3D PDB for CFc000008190 (S-(PGJ2)-glutathione)

SMILES for CFc000008190 (S-(PGJ2)-glutathione)

INCHI for CFc000008190 (S-(PGJ2)-glutathione)

Structure for CFc000008190 (S-(PGJ2)-glutathione)

3D Structure for CFc000008190 (S-(PGJ2)-glutathione)