ChemFOnt: Showing chemical card for cis-12-Oxophytodienoic acid (CFc000282240)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:34:25 UTC

Chemfont ID

CFc000282240

Molecule Identification

Common Name

cis-12-Oxophytodienoic acid

Definition

Cis-12-oxophytodienoic acid, also known as 12-oxo-cis-10, cis-15-phytodienoic acid or 12-oxo-pda, 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. Cis-12-oxophytodienoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-12-oxophytodienoic acid can be found in flaxseed, which makes cis-12-oxophytodienoic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoate	Generator
cis-12-Oxophytodienoic acid	ChEMBL
cis-12-Oxophytodienoate	Generator
12-oxo-PDA	MeSH
12-oxo-cis-10, cis-15-Phytodienoic acid	MeSH
8-(2-(cis-2'-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoic acid	MeSH
OPDA acid	MeSH
12-oxo-Phytodienoic acid	MeSH
12-Oxophytodienoate	MeSH

Chemical Formula

C₁₈H₂₈O₃

Average Molecular Weight

292.419

Monoisotopic Molecular Weight

292.203844762

IUPAC Name

8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

Traditional Name

8-{4-oxo-5-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl}octanoic acid

CAS Registry Number

None

SMILES

[H]\C(CC)=C(/[H])CC1C(CCCCCCCC(O)=O)C=CC1=O

InChI Identifier

InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-

InChI Key

PMTMAFAPLCGXGK-CLTKARDFSA-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

Not Available

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302724)

Food

Herb and spice

Oilseed crop

Flaxseed (FooDB: FOOD00101)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	5.09	ALOGPS
logP	5.08	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	4.78	ChemAxon
pKa (Strongest Basic)	-4.9	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	87.26 m³·mol⁻¹	ChemAxon
Polarizability	34.71 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

HMDB0302724

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005939

KNApSAcK ID

Not Available

Chemspider ID

8510000

KEGG Compound ID

Not Available

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 cis-12-Oxophytodienoic acid (CFc000282240)

MOL for CFc000282240 (cis-12-Oxophytodienoic acid)

3D MOL for CFc000282240 (cis-12-Oxophytodienoic acid)

3D SDF for CFc000282240 (cis-12-Oxophytodienoic acid)

3D-SDF for CFc000282240 (cis-12-Oxophytodienoic acid)

PDB for CFc000282240 (cis-12-Oxophytodienoic acid)

3D PDB for CFc000282240 (cis-12-Oxophytodienoic acid)

SMILES for CFc000282240 (cis-12-Oxophytodienoic acid)

INCHI for CFc000282240 (cis-12-Oxophytodienoic acid)

Structure for CFc000282240 (cis-12-Oxophytodienoic acid)

3D Structure for CFc000282240 (cis-12-Oxophytodienoic acid)