Showing Compound S-(9-Deoxy-delta9,12-PGD2)-glutathione (FDB029273)

Record Information

Version

1.0

Creation date

2011-09-21 01:52:58 UTC

Update date

2015-07-21 06:59:40 UTC

Primary ID

FDB029273

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

S-(9-Deoxy-delta9,12-PGD2)-glutathione

Description

The major dehydration product of prostaglandin D2, 9-deoxy-d9,d12(E)-prostaglandin D2, is a potent cytotoxic compound. Like other cytotoxic prostaglandins, this compound possesses an α,β-unsaturated ketone group to which cytotoxic activity has been attributed. This prostaglandin was found to readily conjugate with glutathione (GSH) in vitro. When 9-deoxy-d9,d12(E)-prostaglandin D2 was incubated with Chinese hamster ovary or hepatoma tissue culture cells, it was rapidly taken up and was recovered in the cell lysate primarily as a GSH conjugate in which the keto group at C-11 and the Δ12 double bond had been reduced. Identification of the GSH conjugate was accomplished by analysis by fast atom bombardment mass spectrometry following purification by high performance liquid chromatography. This GSH conjugate and its cysteinylglycinyl and cysteinyl metabolites were also identified in the cell culture medium. 9-Deoxy-d9,d12(E)-prostaglandin D2 inhibited cell proliferation of these two cell lines in a concentration dependent manner. Depletion of intracellular glutathione by treatment with diethyl maleate and buthionine sulfoximine decreased the amount of intracellular conjugated prostaglandin recovered, and significantly enhanced the antiproliferative effect of 9-deoxy-d9-d12(E)-prostaglandin D2 on the growth of these cell lines in a concentration dependent fashion. Intracellular GSH may modulate the antiproliferative activity of 9-deoxy-Δ9,Δ12(E)-prostaglandin D2 and, possibly, of other cytotoxic prostaglandins. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoate	Generator
(5Z)-7-[(1S,2E)-5-{[(2R)-2-{[(4R)-4-amino-4-carboxy-1-hydroxybutylidene]amino}-2-[(carboxymethyl)-C-hydroxycarbonimidoyl]ethyl]sulphanyl}-2-[(3S)-3-hydroxyoctylidene]-3-oxocyclopentyl]hept-5-enoic acid	Generator
S-(9-Deoxy-δ9,12-PGD2)-glutathione	Generator

Showing 1 to 4 of 4 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	-1	ALOGPS
logP	-0.92	ChemAxon
logS	-4.7	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	164.95 m³·mol⁻¹	ChemAxon
Polarizability	68.49 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-[(1S,2E)-5-{[(2R)-2-[(4R)-4-amino-4-carboxybutanamido]-2-[(carboxymethyl)carbamoyl]ethyl]sulfanyl}-2-[(3S)-3-hydroxyoctylidene]-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/h4,7,13,19,21-23,25,34H,2-3,5-6,8-12,14-18,31H2,1H3,(H,32,41)(H,33,36)(H,37,38)(H,39,40)(H,42,43)/b7-4-,20-13+/t19-,21-,22+,23-,25?/m0/s1

InChI Key

RPHLHZIDWIFTII-RJQMMLODSA-N

Isomeric SMILES

CCCCC[C@H](O)C\C=C1/[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
Glutamine or derivatives
N-acyl-alpha amino acid or derivatives
N-acyl-alpha-amino acid
Alpha-amino acid amide
Cysteine or derivatives
Alpha-amino acid
N-substituted-alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Tricarboxylic acid or derivatives
N-acyl-amine
Fatty acyl
Fatty amide
Cyclopentanol
Cyclic alcohol
Secondary alcohol
Amino acid
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
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-(9-Deoxy-delta9,12-PGD2)-glutathione, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00r5-2100091000-fc3f2ec8b2bcc776a36d	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_15, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	S-(9-Deoxy-delta9,12-PGD2)-glutathione, TMS_2_16, 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	splash10-05i1-0111179000-0fc19bc8865c63212e38	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004s-5801591000-016e9a8877d2f1872558	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-070i-9640430000-4a917df721ce22c3fdd1	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00xv-0017059000-db67d08d5927b114bdae	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ba-1009010000-77f5685d6bf480fcd767	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-4903000000-d59fff148aca87e4980c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0avl-0016119000-db336fdfdabc63420580	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-7659657000-a6ae269151b28769ace2	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9200210000-eff1088b6c8034713cf8	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-006x-0020009000-164f0884dafda8f7808d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0096-1930012000-f9b63e648f7d2daa319d	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9700000000-782640093e9d989b10c9	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

53481598

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB13058

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

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Files

MSDS

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References

Synthesis Reference

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General Reference

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Content Reference

Showing Compound S-(9-Deoxy-delta9,12-PGD2)-glutathione (FDB029273)

Structure for FDB029273 (S-(9-Deoxy-delta9,12-PGD2)-glutathione)