ChemFOnt: Showing chemical card for 7-Epi-12-hydroxyjasmonic acid (CFc000283265)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:36:22 UTC

Chemfont ID

CFc000283265

Molecule Identification

Common Name

7-Epi-12-hydroxyjasmonic acid

Definition

7-epi-12-hydroxyjasmonic acid, also known as (+)-12-hydroxy-7-isojasmonate, 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-epi-12-hydroxyjasmonic acid is considered to be an octadecanoid lipid molecule. 7-epi-12-hydroxyjasmonic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 7-epi-12-hydroxyjasmonic acid can be synthesized from (+)-7-isojasmonic acid. 7-epi-12-hydroxyjasmonic acid can also be synthesized into N-[(+)-12-hydroxy-7-isojasmonyl]-L-isoleucine and methyl tuberonate. 7-epi-12-hydroxyjasmonic acid can be found in potato, which makes 7-epi-12-hydroxyjasmonic acid a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-12-Hydroxy-7-isojasmonic acid	ChEBI
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetic acid	ChEBI
12-Hydroxy-epi-jasmonic acid	ChEBI
(+)-12-Hydroxy-7-isojasmonate	Generator
(1R,2S)-3-oxo-2-(5'-Hydroxy-2'z-pentenyl)-cyclopentaneacetate	Generator
12-Hydroxy-epi-jasmonate	Generator
Tuberonate	Generator
7-Epi-12-hydroxyjasmonate	Generator

Chemical Formula

C₁₂H₁₈O₄

Average Molecular Weight

226.2689

Monoisotopic Molecular Weight

226.120509064

IUPAC Name

2-[(1R,2S)-2-[(2Z)-5-hydroxypent-2-en-1-yl]-3-oxocyclopentyl]acetic acid

Traditional Name

tuberonic acid

CAS Registry Number

124649-26-9

SMILES

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

InChI Identifier

InChI=1S/C12H18O4/c13-7-3-1-2-4-10-9(8-12(15)16)5-6-11(10)14/h1-2,9-10,13H,3-8H2,(H,15,16)/b2-1-/t9-,10+/m1/s1

InChI Key

RZGFUGXQKMEMOO-SZXTZRQCSA-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
Fatty alcohol
Cyclic ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Jasmonic acids (LMFA02020007 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0303749)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.28 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.98	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	4.46	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	60.49 m³·mol⁻¹	ChemAxon
Polarizability	23.9 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

HMDB0303749

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB020508

KNApSAcK ID

C00000221

Chemspider ID

4947920

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6443968

PDB ID

Not Available

ChEBI ID

133220

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 7-Epi-12-hydroxyjasmonic acid (CFc000283265)

MOL for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

3D MOL for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

3D SDF for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

3D-SDF for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

PDB for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

3D PDB for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

SMILES for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

INCHI for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

Structure for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)

3D Structure for CFc000283265 (7-Epi-12-hydroxyjasmonic acid)