ChemFOnt: Showing chemical card for 8-iso-PGF3a (CFc000001432)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:04 UTC

Chemfont ID

CFc000001432

Molecule Identification

Common Name

8-iso-PGF3a

Definition

8-iso-PGF3alpha is an isoprostane with an antiaggregatory action in human blood. Isoprostanes (IsoPs) are formed in vivo from the free radical-catalyzed peroxidation of arachidonate independent of cyclooxygenase (COX). Although the structures of these compounds are very similar to COX-derived prostaglandins (PGs), an important distinction between IsoPs and PGs is that IsoP bicycloendoperoxide intermediates contain side chains that are predominantly (>90%) oriented cis in relation to the prostane ring because the generation of these intermediates is favored kinetically. In contrast to other types of prostanoids, E2/D2-IsoPs are beta-hydroxyketone-containing compounds that can undergo reversible keto-enol tautomerization under both acidic and basic conditions, allowing rearrangement of the side chains that are initially cis to the more stable trans-configuration. (PMID: 12746435 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₀H₃₂O₅

Average Molecular Weight

352.4651

Monoisotopic Molecular Weight

352.224974134

IUPAC Name

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

Traditional Name

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

CAS Registry Number

7045-31-0

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/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/h3-4,6-7,12-13,15-19,21-23H,2,5,8-11,14H2,1H3,(H,24,25)/t15-,16-,17+,18-,19+/m0/s1

InChI Key

SAKGBZWJAIABSY-QXCZDIPSSA-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
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: HMDB0002132)
Membrane (HMDB: HMDB0002132)

Source

Exogenous

Exogenous (HMDB: HMDB0002132)

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: HMDB0002132)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	3.7	ALOGPS
logP	2.25	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	101.59 m³·mol⁻¹	ChemAxon
Polarizability	40.91 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

FDB022859

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

3246910

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Beal, Philip F., III; Fonken, Gunther S.; Pike, John E. Microbiological conversions of unsaturated fatty acids. (1965), 34 pp. BE 659984 19650819 CAN 64:87998 AN 1966:87998

Showing chemical card for 8-iso-PGF3a (CFc000001432)

MOL for CFc000001432 (8-iso-PGF3a)

3D MOL for CFc000001432 (8-iso-PGF3a)

3D SDF for CFc000001432 (8-iso-PGF3a)

3D-SDF for CFc000001432 (8-iso-PGF3a)

PDB for CFc000001432 (8-iso-PGF3a)

3D PDB for CFc000001432 (8-iso-PGF3a)

SMILES for CFc000001432 (8-iso-PGF3a)

INCHI for CFc000001432 (8-iso-PGF3a)

Structure for CFc000001432 (8-iso-PGF3a)

3D Structure for CFc000001432 (8-iso-PGF3a)