ChemFOnt: Showing chemical card for 3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid (CFc000281321)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:32:35 UTC

Chemfont ID

CFc000281321

Molecule Identification

Common Name

3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid

Definition

3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid, also known as opc-8:0, is a member of the class of compounds known as prostaglandins and related compounds. Prostaglandins and related compounds 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. Thus, 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid is considered to be an octadecanoid lipid molecule. 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid can be found in common wheat, corn, eggplant, and flaxseed, which makes 3-oxo-2-(2-entenyl)cyclopentaneoctanoic acid a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
OPC-8:0	Kegg
8-[(1S,2S)-3-oxo-2-[(2Z)-Pent-2-en-1-yl]cyclopentyl]octanoate	Generator
3-oxo-2-(2-Entenyl)cyclopentaneoctanoate	Generator

Chemical Formula

C₁₈H₃₀O₃

Average Molecular Weight

294.429

Monoisotopic Molecular Weight

294.219494826

IUPAC Name

8-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]octanoic acid

Traditional Name

8-[(1S,2S)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]octanoic acid

CAS Registry Number

204135-86-4

SMILES

CC\C=C/C[C@H]1[C@@H](CCCCCCCC(O)=O)CCC1=O

InChI Identifier

InChI=1S/C18H30O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,15-16H,2,4-6,8-14H2,1H3,(H,20,21)/b7-3-/t15-,16-/m0/s1

InChI Key

BZXZFDKIRZBJEP-JMTMCXQRSA-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
Medium-chain fatty acid
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

12-oxophytodienoic acid metabolites (LMFA02010007 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301805)

Food

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Common wheat (FooDB: FOOD00187)

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0027 g/L	ALOGPS
logP	5.2	ALOGPS
logP	5.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.72	ChemAxon
pKa (Strongest Basic)	-7.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	86.16 m³·mol⁻¹	ChemAxon
Polarizability	35.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0301805

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001433

KNApSAcK ID

Not Available

Chemspider ID

4444310

KEGG Compound ID

C04780

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid (CFc000281321)

MOL for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

3D MOL for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

3D SDF for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

3D-SDF for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

PDB for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

3D PDB for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

SMILES for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

INCHI for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

Structure for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)

3D Structure for CFc000281321 (3-Oxo-2-(2-entenyl)cyclopentaneoctanoic acid)