ChemFOnt: Showing chemical card for 7-Epijasmonic acid (CFc000283320)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:28 UTC

Chemfont ID

CFc000283320

Molecule Identification

Common Name

7-Epijasmonic acid

Definition

7-epijasmonic acid, also known as (+)-epijasmonate, is a member of the class of compounds known as jasmonic acids. Jasmonic acids are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety. Thus, 7-epijasmonic acid is considered to be an octadecanoid lipid molecule. 7-epijasmonic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 7-epijasmonic acid can be found in a number of food items such as broad bean, flaxseed, corn, and eggplant, which makes 7-epijasmonic acid a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Epijasmonic acid	ChEBI
2-[(1R,2S)-3-oxo-2-[(Z)-Pent-2-enyl]cyclopentyl]acetic acid	ChEBI
(+)-Epijasmonate	Generator
2-[(1R,2S)-3-oxo-2-[(Z)-Pent-2-enyl]cyclopentyl]acetate	Generator
(+)-7-Isojasmonate	Generator
7-Epijasmonate	Generator

Chemical Formula

C₁₂H₁₈O₃

Average Molecular Weight

210.2695

Monoisotopic Molecular Weight

210.125594442

IUPAC Name

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

Traditional Name

(+)-7-iso-jasmonic acid

CAS Registry Number

None

SMILES

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

InChI Identifier

InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10+/m1/s1

InChI Key

ZNJFBWYDHIGLCU-QKMQQOOLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as jasmonic acids. These are lipids containing or derived from a jasmonic acid, with a structure characterized by the presence of an alkene chain linked to a 2-(3-oxocyclopentyl)acetic acid moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Jasmonic acids

Alternative Parents

Substituents

Jasmonic 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:18435 )
oxylipin (CHEBI:18435 )
Jasmonic acids (C16317 )
Jasmonic acids (LMFA02020003 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303804)

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)

Pulse

Bean

Broad bean (FooDB: FOOD00197)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.92 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.41	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.71	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	5	ChemAxon
Refractivity	58.56 m³·mol⁻¹	ChemAxon
Polarizability	23.25 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

HMDB0303804

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021719

KNApSAcK ID

Not Available

Chemspider ID

5584839

KEGG Compound ID

C16317

BioCyc ID

CPD-731

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

18435

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 7-Epijasmonic acid (CFc000283320)

MOL for CFc000283320 (7-Epijasmonic acid)

3D MOL for CFc000283320 (7-Epijasmonic acid)

3D SDF for CFc000283320 (7-Epijasmonic acid)

3D-SDF for CFc000283320 (7-Epijasmonic acid)

PDB for CFc000283320 (7-Epijasmonic acid)

3D PDB for CFc000283320 (7-Epijasmonic acid)

SMILES for CFc000283320 (7-Epijasmonic acid)

INCHI for CFc000283320 (7-Epijasmonic acid)

Structure for CFc000283320 (7-Epijasmonic acid)

3D Structure for CFc000283320 (7-Epijasmonic acid)