Showing Compound Jasmonic acid (FDB015493)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:52 UTC

Update date

2020-09-17 15:41:51 UTC

Primary ID

FDB015493

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Jasmonic acid

Description

Jasmonic acid, also known as jasmonate, 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. Based on a literature review a significant number of articles have been published on Jasmonic acid.

CAS Number

59366-47-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-Jasmonic acid	ChEBI
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetic acid	ChEBI
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetic acid	ChEBI
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetate	ChEBI
Jasmonate	ChEBI
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetic acid	Kegg
(-)-Jasmonate	Kegg
(1R,2R)-3-oxo-2-(2Z)-2-Penten-ylcyclopentanacetate	Generator
(1R,2R)-3-oxo-2-(Pent-2Z-enyl)-cyclopentaneacetate	Generator
2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetic acid	Generator
{(1R,2R)-3-oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetate	Generator
7-Epi-jasmonic acid	MeSH
(Z)-trans-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
[1R-[1alpha,2beta(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
[1R-[1α,2β(Z)]]-3-Oxo-2-(2-pentenyl)-cyclopentaneacetic acid	PhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetic acid	PhytoBank
(1R,2R)-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic acid	PhytoBank
(1R,2R)-Jasmonic acid	PhytoBank
(3R,7R)(-)-Jasmonic acid	PhytoBank
JA	PhytoBank
(1R,2R)-3-oxo-2-(2Z)-2-penten-ylcyclopentanacetic acid	biospider
(1R,2R)-3-oxo-2-(pent-2Z-enyl)-cyclopentaneacetic acid	biospider
3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid	biospider
3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid, 9CI, 8CI	db_source
3-Oxo-2-(2Z-pentenyl)cyclotentylacetic acid	biospider
Jasmonic acid	db_source

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	22.93 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

Chemical Formula

C12H18O3

IUPAC name

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

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-HWKXXFMVSA-N

Isomeric SMILES

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

Average Molecular Weight

210.2695

Monoisotopic Molecular Weight

210.125594442

Classification

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 monocarboxylic acid (CHEBI:18292 )
Jasmonic acids (C08491 )
Fatty acids (C08491 )
Jasmonic acids (LMFA02020001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 68.55%; H 8.63%; O 22.83%	DFC
Melting Point	Not Available
Boiling Point	Bp0.001 125°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]D -83.5 (c, 0.97 in CHCl3)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	n19D 1.4885	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Jasmonic acid, 1 TMS, GC-MS Spectrum	splash10-0gc1-3910000000-fc5414b8972660237107	Spectrum
GC-MS	Jasmonic acid, 2 TMS, GC-MS Spectrum	splash10-00di-1960000000-15b13e2686e63dbec8ac	Spectrum
GC-MS	Jasmonic acid, 1 MEOX; 1 TMS, GC-MS Spectrum	splash10-0fur-5920000000-56a3bfca05d9c2a0fb58	Spectrum
Predicted GC-MS	Jasmonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-053r-6900000000-6dbc88cef2dd120798d4	Spectrum
Predicted GC-MS	Jasmonic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fy9-9450000000-0d94fd142631685c4b7b	Spectrum
Predicted GC-MS	Jasmonic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - NA 35V, negative	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-0a4i-9000000000-2d9af7143ec50cf2d0d0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - NA , negative	splash10-066r-2930000000-fa66a377eb1b1fca8f5c	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, negative	splash10-014i-0900000000-6a243c2851549d3933a0	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 14V, negative	splash10-0a4i-0090000000-32f15e4d1ce43554b369	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, negative	splash10-0a4i-1090000000-0eea64532a321522940a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0a4i-1090000000-dcd76ae3b160ae066dac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, negative	splash10-0a4i-1090000000-04497dd8bc966faba21c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-2090000000-1aa739b17227b8175964	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-2090000000-c3df319b32792e702631	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-0a4i-4090000000-aa4a7a821d19b44f0cd5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-5090000000-82f8a4dbefd75fc32972	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-0a4i-6090000000-910ea32926dde4e482cb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-0a4i-9080000000-56dfbbb726baa8bf1ca7	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-9030000000-a7e12bbe5010ba971a9c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0a4i-9010000000-8184a91f4d8f167c8442	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0a4i-9000000000-dcce12c198d67bee2dbe	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0a4i-9000000000-47b37bf1431de1c71ac6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, negative	splash10-0a4i-9000000000-b8485c47ca16500d47c9	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-1940000000-cbdd7749a0552b6dcb18	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015c-9700000000-4b9efb60332c4d520667	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f9x-9100000000-e7e90e131d7ac7d27a35	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0aor-0690000000-d03d837380060d855a00	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0aor-3950000000-30695cc3cca6390fcace	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4m-9400000000-c0d8ea2d3164bace07b2	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4444606

ChEMBL ID

Not Available

KEGG Compound ID

C08491

Pubchem Compound ID

5281166

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB32797

CRC / DFC (Dictionary of Food Compounds) ID

KCT55-C:KCT55-C

EAFUS ID

Not Available

Dr. Duke ID

JASMONIC-ACID|(-)-JASMONIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00000218

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Jasmonic_acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Fungicide	24127	An agent that kills or inhibits the growth of fungi, playing a biological role in preventing fungal infections. Therapeutically, it is used to treat fungal diseases, with key medical applications including athlete's foot, ringworm, and candidiasis, as well as agricultural uses to protect crops from fungal damage.	DUKE
Phytohormonal	26158	A plant-derived hormone regulator, mimicking human hormones to balance bodily functions. Its biological role involves regulating growth, development, and stress response. Therapeutically, it has applications in menopause relief, anti-aging, and stress management, with key medical uses including hormone replacement therapy and alleviating menopausal symptoms.	DUKE