ChemFOnt: Showing chemical card for 12-oxo-PDA (CFc000281320)

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

CFc000281320

Molecule Identification

Common Name

12-oxo-PDA

Definition

12-oxo-pda, also known as (15z)-12-oxophyto-10,15-dienoate or 12-oxo-10,15(Z)-phytodienoic acid, 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, 12-oxo-pda is considered to be an octadecanoid lipid molecule. 12-oxo-pda is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 12-oxo-pda can be found in corn, which makes 12-oxo-pda a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(15Z)-12-Oxophyto-10,15-dienoate	ChEBI
12-OPDA	ChEBI
12-oxo-10,15(Z)-Phytodienoic acid	ChEBI
12-Oxophytodienoic acid	ChEBI
4-oxo-5-(2-Pentenyl)-2-cyclopentene-1-octanoic acid	ChEBI
8-(2-(cis-2'-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoic acid	ChEBI
9(S),13(S)-12-oxo-PDA	ChEBI
OPDA	ChEBI
12-oxo-10,15(Z)-Phytodienoate	Generator
12-Oxophytodienoate	Generator
4-oxo-5-(2-Pentenyl)-2-cyclopentene-1-octanoate	Generator
8-(2-(cis-2'-Pentenyl)-3-oxo-cis-4-cyclopentenyl)octanoate	Generator
12-oxo-PDA	MeSH
OPDA acid	MeSH
12-oxo-cis-10, cis-15-Phytodienoic acid	MeSH
(15Z)-12-oxophyto-10,15-Dienoic acid	Generator, KEGG

Chemical Formula

C₁₈H₂₈O₃

Average Molecular Weight

292.4131

Monoisotopic Molecular Weight

292.203844762

IUPAC Name

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

Traditional Name

12-oxo-phytodienoic acid

CAS Registry Number

85551-10-6

SMILES

CC\C=C/C[C@H]1[C@@H](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-/t15-,16-/m0/s1

InChI Key

PMTMAFAPLCGXGK-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

oxo carboxylic acid (CHEBI:15560 )
carbocyclic fatty acid (CHEBI:15560 )
unsaturated fatty acid (CHEBI:15560 )
12-oxophytodienoic acid metabolites (C01226 )
12-oxophytodienoic acid metabolites (LMFA02010001 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0301804)

Food

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)

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	35.15 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

HMDB0301804

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001432

KNApSAcK ID

Not Available

Chemspider ID

4444088

KEGG Compound ID

C01226

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280411

PDB ID

Not Available

ChEBI ID

15560

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 12-oxo-PDA (CFc000281320)

MOL for CFc000281320 (12-oxo-PDA)

3D MOL for CFc000281320 (12-oxo-PDA)

3D SDF for CFc000281320 (12-oxo-PDA)

3D-SDF for CFc000281320 (12-oxo-PDA)

PDB for CFc000281320 (12-oxo-PDA)

3D PDB for CFc000281320 (12-oxo-PDA)

SMILES for CFc000281320 (12-oxo-PDA)

INCHI for CFc000281320 (12-oxo-PDA)

Structure for CFc000281320 (12-oxo-PDA)

3D Structure for CFc000281320 (12-oxo-PDA)