Jasmonic acid

Details

• Internal ID: db2ff335-55e5-4355-b2d0-2ee93e769238
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives > Jasmonic acids
• IUPAC Name: 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid
• SMILES (Canonical): CCC=CCC1C(CCC1=O)CC(=O)O
• SMILES (Isomeric): CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
• InChI: 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
• Popularity: 3,780 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.27 g/mol
• Exact Mass: 210.125594432 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 2.41
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 6894-38-8
• Jasmonate
• (-)-Jasmonic acid
• trans-Jasmonic Acid
• 77026-92-7
• (+/-)-Jasmonic acid
• 3-Oxo-2-(2-pentenyl)cyclopentaneacetic acid
• trans-Jasmonic Acid (1 g/ 10 mL Ethanol)
• (3R,7R)-Jasmonic acid
• UNII-6RI5N05OWW
• {(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acid
• 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid
• 6RI5N05OWW
• (1R,2R)-3-oxo-2-(pent-2Z-enyl)-cyclopentaneacetic acid
• CHEMBL449572
• CHEBI:18292
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, (1R,2R)-
• TNP00291
• (-)-jasmonate
• {(1R,2R)-3-Oxo-2-[(Z)pent-2-enyl]cyclopent-2-enyl}acetic acid
• (Z)-2-(2-(but-2-en-1-yl)-4-oxocyclopentyl)-acetic acid
• 2-{(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl}acetate
• ()-Jasmonic acid
• trans-JasmonicAcid
• JA
• bmse000525
• JASMONIC ACID [MI]
• SCHEMBL114054
• 2-((1R,2R)-2-((Z)-But-2-en-1-yl)-4-oxocyclopentyl)acetic acid
• 2-((1S,2S)-3-Oxo -2-((Z)-pent-2-en-1-yl)cyclopentyl)acetic acid
• DTXSID4037665
• (3R,7R)-(?)-Jasmonic acid
• 2-[(1R,2R)-2-((2Z)pent-2-enyl)-3-oxocyclopentyl]acetic acid
• CMC_7387
• BDBM50396691
• CMC_13965
• LMFA02020001
• HY-122464A
• NCGC00017349-01
• NCGC00017349-02
• NCGC00142527-01
• LS-186703
• LS-187405
• CS-0135945
• A14333
• C08491
• Q415311
• J-502581
• 3-oxo-2R-(2Z)2-penten-1R-yl-cyclopentaneacetic acid
• 3-Oxo-2R-(2Z)2-penten-1R-ylcyclopentaneacetic acid
• E9BF63E8-55FE-4051-AE00-04B002D8CE1F
• (1R,2R)-3-oxo-2-(2Z)-2-penten-ylcyclopentanacetic acid
• (1r,2r)-3-oxo-2-(2z)-2-pentenyl-cyclopentaneacetic acid
• (1R,2R)-3-Oxo-2-(2Z)-2-penten-1-ylcyclopentaneacetic acid
• ()-1alpha,2beta-3-Oxo-2-(cis-2-pentenyl)cyclopentaneacetic acid
• (-)-1alpha,2beta-3-Oxo-2-(cis-2-pentenyl)cyclopentaneacetic acid
• (1R,2R)-3-OXO-2-(2Z)-2-PENTENYLCYCLOPENTANEACETIC ACID
• (1R,2R)-3-OXO-2-(Z)-PENT-2-ENYLCYCLOPENTYLACETIC ACID
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, (Z)-trans- (8CI)
• cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-pentenyl]-, (1R,2R)-
• 2-[(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl]acetic acid
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, [1R-[1alpha,2beta(Z)]]-
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, (1R,2R)- (9CI)
• Cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-penten-1-yl]-, (1R,2R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9842	98.42%
Caco-2	-	0.5267	52.67%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8366	83.66%
OATP2B1 inhibitior	-	0.8466	84.66%
OATP1B1 inhibitior	+	0.9135	91.35%
OATP1B3 inhibitior	+	0.9507	95.07%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8848	88.48%
P-glycoprotein inhibitior	-	0.9857	98.57%
P-glycoprotein substrate	-	0.8766	87.66%
CYP3A4 substrate	-	0.6130	61.30%
CYP2C9 substrate	+	0.5862	58.62%
CYP2D6 substrate	-	0.8802	88.02%
CYP3A4 inhibition	-	0.9093	90.93%
CYP2C9 inhibition	-	0.9407	94.07%
CYP2C19 inhibition	-	0.9292	92.92%
CYP2D6 inhibition	-	0.9251	92.51%
CYP1A2 inhibition	-	0.9386	93.86%
CYP2C8 inhibition	-	0.9465	94.65%
CYP inhibitory promiscuity	-	0.9631	96.31%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9000	90.00%
Carcinogenicity (trinary)	Non-required	0.7147	71.47%
Eye corrosion	-	0.9560	95.60%
Eye irritation	-	0.6020	60.20%
Skin irritation	+	0.5779	57.79%
Skin corrosion	-	0.8611	86.11%
Ames mutagenesis	-	0.7100	71.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7140	71.40%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	+	0.6926	69.26%
skin sensitisation	-	0.6455	64.55%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.7923	79.23%
Acute Oral Toxicity (c)	III	0.7793	77.93%
Estrogen receptor binding	-	0.8986	89.86%
Androgen receptor binding	-	0.5636	56.36%
Thyroid receptor binding	-	0.8573	85.73%
Glucocorticoid receptor binding	-	0.5704	57.04%
Aromatase binding	-	0.8346	83.46%
PPAR gamma	-	0.7279	72.79%
Honey bee toxicity	-	0.9775	97.75%
Biodegradation	-	0.5500	55.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9093	90.93%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5847	P52895	Aldo-keto reductase family 1 member C2	18000 nM	Ki	PMID: 22877157
CHEMBL4999	P17516	Aldo-keto reductase family 1 member C4	37000 nM	Ki	PMID: 22877157

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.77%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.60%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	85.96%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.34%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.19%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.27%	97.25%

Plants that contains it

• Arabidopsis thaliana
• Brassica napus
• Carthamus arborescens
• Cleyera japonica
• Equisetum arvense
• Helianthus tuberosus
• Hordeum vulgare
• Mimosa pudica
• Oryza officinalis
• Phaseolus lunatus
• Picradeniopsis woodhousei
• Vicia faba

Cross-Links

• PubChem: 5281166
• NPASS: NPC60120
• ChEMBL: CHEMBL449572
• LOTUS: LTS0196594
• wikiData: Q104994420