ChemFOnt: Showing chemical card for 8-iso-13,14-dihydro-15-keto-PGF2a (CFc000002811)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:47 UTC

Chemfont ID

CFc000002811

Molecule Identification

Common Name

8-iso-13,14-dihydro-15-keto-PGF2a

Definition

8-iso-13,14-dihydro-15-keto-PGF2a is an isoprostane. Isoprostanes are a family of prostaglandin (PG) isomers generated by free radical-catalysed peroxidation and then rearrangement of arachidonic acid. In addition, isoprostanes can be produced by cyclo-oxygenase (COX) dependent pathways. Several cell types have been shown to release increased levels of the F2 isoprostane, 8-iso PGF2alpha, when stimulated with inflammatory mediators or subjected to oxidative stress in vitro. Furthermore, 8-iso PGF2alpha levels are elevated in rats in vivo when prooxidant conditions are induced experimentally. Similarly, elevated isoprostane production has been demonstrated in clinical conditions characterized by oxidant stress including diabetes, alcoholism, paraquat poisoning, myocardial reperfusion, critical illness, pre-eclampsia and smoking. Consequently, the measurement of 8-iso PGF2alpha in plasma and urine has been proposed as a relevant and convenient method to monitor oxidant stress in man. (PMID: 11309241 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₄O₅

Average Molecular Weight

354.481

Monoisotopic Molecular Weight

354.240624198

IUPAC Name

7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

Traditional Name

7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid

CAS Registry Number

191919-02-5

SMILES

[H][C@@]1(O)C[C@]([H])(O)[C@@]([H])(CC=CCCCC(O)=O)[C@@]1([H])CCC(=O)CCCCC

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h4,7,16-19,22-23H,2-3,5-6,8-14H2,1H3,(H,24,25)/t16-,17+,18-,19+/m0/s1

InChI Key

VKTIONYPMSCHQI-ZSYWTGECSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0006562)
Membrane (HMDB: HMDB0006562)

Source

Exogenous

Exogenous (HMDB: HMDB0006562)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006562)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.12	ALOGPS
logP	3.02	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.31	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.48 m³·mol⁻¹	ChemAxon
Polarizability	41.76 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023973

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

METLIN ID

Not Available

PubChem Compound

3246907

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 8-iso-13,14-dihydro-15-keto-PGF2a (CFc000002811)

MOL for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

3D MOL for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

3D SDF for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

3D-SDF for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

PDB for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

3D PDB for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

SMILES for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

INCHI for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

Structure for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)

3D Structure for CFc000002811 (8-iso-13,14-dihydro-15-keto-PGF2a)