Showing Compound S-(PGJ2)-glutathione (FDB029278)

Record Information

Version

1.0

Creation date

2011-09-21 01:53:02 UTC

Update date

2015-07-21 06:59:40 UTC

Primary ID

FDB029278

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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
9-(S-Glutathionyl)-prostaglandin J(,2)	HMDB
9-(S-glutathionyl)-prostaglandin J(,2)	hmdb
GSPGJ2	HMDB

Showing 1 to 6 of 6 entries

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

Chemical Formula

C30H47N3O10S

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

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

Isomeric 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

Average Molecular Weight

641.773

Monoisotopic Molecular Weight

641.298215429

Classification

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

Ontology

Disposition

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	S-(PGJ2)-glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r7-4100091000-46952d73cf49f21d796c	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(PGJ2)-glutathione, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05i1-0011179000-3a9d05d089ebd11bca96	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004s-3900461000-7a9b9f50ccdb2691cf24	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0avi-9301310000-088da1467bdd55576e67	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xv-0016059000-846862813ec4ca3bccb0	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-0009010000-c6932bc4c2554632d9cd	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-4903000000-3917652d16d7a5c14d59	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0avi-0015119000-b1c1a7345ce9ce89d55e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bvj-2358879000-bf39e0dcc8c261c2fe94	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9400200000-eab9494ac2f19dc38772	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0020009000-0eeffb6f03dfce4e2814	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0096-1930012000-a0f5bb24beb716a6f233	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9700000000-e10bf6a8bbfc904f8e17	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53481603

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB13063

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound S-(PGJ2)-glutathione (FDB029278)

Structure for FDB029278 (S-(PGJ2)-glutathione)