Methyl jasmonate

Details

• Internal ID: 6e5abf56-4cca-43ff-a46b-e80c13539c5c
• Taxonomy: Lipids and lipid-like molecules > Fatty Acyls > Lineolic acids and derivatives > Jasmonic acids
• IUPAC Name: methyl 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
• SMILES (Canonical): CCC=CCC1C(CCC1=O)CC(=O)OC
• SMILES (Isomeric): CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)OC
• InChI: InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1
• InChI Key: GEWDNTWNSAZUDX-WQMVXFAESA-N
• Popularity: 7,559 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₃H₂₀O₃
• Molecular Weight: 224.30 g/mol
• Exact Mass: 224.14124450 g/mol
• Topological Polar Surface Area (TPSA): 43.40 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 2.50
• H-Bond Acceptor: 3
• H-Bond Donor: 0
• Rotatable Bonds: 5

Synonyms

• 1211-29-6
• (-)-Methyl jasmonate
• Methyl cis-jasmonate
• Methyl 2-((1R,2R)-3-oxo-2-((Z)-pent-2-en-1-yl)cyclopentyl)acetate
• methyl (-)-jasmonate
• Jasmonic acid methyl ester
• (-)-Jasmonic acid methyl ester
• (3R,7R)-Methyl jasmonate
• Methyl dl-jasmonate
• Methyl jasmonic acid
• CHEBI:15929
• Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetate
• 3-oxo-2-(2-pentenyl)cyclopentaneacetic acid methyl ester
• UNII-900N171A0F
• HSDB 8131
• methyl 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
• Z-Methyl jasmonoate
• EINECS 214-918-6
• EINECS 243-497-1
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2R)-
• 900N171A0F
• (-)-Jasmonic acid, methyl ester (trans)
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, (Z)-trans-
• Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate, (1R-(1alpha,2beta(Z)))-
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-
• Methyljasmonate
• methyl 2-((1R,2R)-3-oxo-2-pent-2Z-enyl)cyclopentyl)acetate
• Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate, (Z)-trans-
• (+-)-Cyclopentaneacetic acid, 3-oxo-trans-2-(cis-2-pentenyl), methyl ester
• Methyl (1R-(1alpha,2beta(Z)))-3-oxo-2-(pent-2-enyl)cyclopentaneacetate
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, (1R-(1alpha,2beta(Z)))-
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, (1theta-(1alpha,2beta(Z)))-
• Cyclopentaneacetic acid, 3-oxo-trans-2-(cis-2-pentenyl), methyl ester
• Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate
• 39924-52-2
• FEMA No. 3410
• Methyl [1R-[1alpha,2beta(Z)]]-3-oxo-2-(pent-2-enyl)cyclopentaneacetate
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1R-[1alpha,2beta(Z)]]-
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2R)-rel-
• 20073-13-6
• CYCLOPENTANEACETIC ACID, 3-OXO-2-(2-PENTENYL)-, METHYL ESTER, (1R-(1.ALPHA.,2.BETA.(Z)))-
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1R-[1.alpha.,2.beta.(Z)]]-
• SCHEMBL36186
• METHYL JASMONATE [FHFI]
• CHEMBL2139332
• DTXSID3036731
• Methyl [1alpha,2beta(Z)]-(+-)-3-oxo-2-(pent-2-enyl)cyclopentaneacetate
• FEMA 3410
• (3R,7R)-(?)-Methyl jasmonate
• CMC_7389
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1.alpha.,2.beta.(Z)]-(.+-.)-
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, [1.alpha.,2.beta.(Z)]-(.+.)-
• BDBM50509748
• CMC_13964
• LMFA02020010
• AKOS015950850
• JASMONIC ACID METHYL ESTER [MI]
• AS-75742
• HY-135663
• CS-0113712
• D94878
• A891945
• Q26840883
• CYCLOPENTANEACETATE, 3-OXO-2-(2-PENTENYL)-, METHYL
• 8171C3E0-B789-4211-B5C1-88C6B260AE3C
• Cyclopentaneaceticacid,3-oxo-2-(2Z)-2-penten-1-yl-,methyl ester,(1R,2R)-
• Methyl (1alpha,2beta(Z))-(1)-3-oxo-2-(pent-2-enyl)cyclopentaneacetate
• methyl {(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetate
• Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester, (Z)-trans- (8CI)
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-rel-
• Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, methyl ester, (1R,2R)- (9CI)
• Cyclopentaneacetic acid, 3-oxo-2-[(2Z)-2-pentenyl]-, methyl ester, (1R,2R)-
• Cyclopentaneaceticacid, 3-oxo-2-(2Z)-2-penten-1-yl-, methyl ester, (1R,2R)-
• methyl (1R - (1a,2b(Z))) - 3 - oxo - 2 - (pent - 2 - enyl)cyclopentaneacetate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9950	99.50%
Caco-2	+	0.7920	79.20%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8168	81.68%
OATP2B1 inhibitior	-	0.8503	85.03%
OATP1B1 inhibitior	+	0.9099	90.99%
OATP1B3 inhibitior	+	0.9552	95.52%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.8149	81.49%
P-glycoprotein inhibitior	-	0.9658	96.58%
P-glycoprotein substrate	-	0.7718	77.18%
CYP3A4 substrate	-	0.5054	50.54%
CYP2C9 substrate	-	0.8121	81.21%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.9364	93.64%
CYP2C9 inhibition	-	0.9396	93.96%
CYP2C19 inhibition	-	0.8582	85.82%
CYP2D6 inhibition	-	0.8824	88.24%
CYP1A2 inhibition	-	0.8697	86.97%
CYP2C8 inhibition	-	0.8680	86.80%
CYP inhibitory promiscuity	-	0.8789	87.89%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8823	88.23%
Carcinogenicity (trinary)	Non-required	0.7448	74.48%
Eye corrosion	-	0.9226	92.26%
Eye irritation	-	0.8528	85.28%
Skin irritation	-	0.8133	81.33%
Skin corrosion	-	0.9826	98.26%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5307	53.07%
Micronuclear	-	0.9200	92.00%
Hepatotoxicity	+	0.5656	56.56%
skin sensitisation	-	0.7640	76.40%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	-	0.6444	64.44%
Mitochondrial toxicity	-	0.8250	82.50%
Nephrotoxicity	-	0.6118	61.18%
Acute Oral Toxicity (c)	III	0.8234	82.34%
Estrogen receptor binding	-	0.8900	89.00%
Androgen receptor binding	-	0.5183	51.83%
Thyroid receptor binding	-	0.8077	80.77%
Glucocorticoid receptor binding	-	0.4829	48.29%
Aromatase binding	-	0.7848	78.48%
PPAR gamma	-	0.8302	83.02%
Honey bee toxicity	-	0.9374	93.74%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	+	0.9697	96.97%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.77%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.74%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.92%	95.56%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.83%	94.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.78%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.98%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.76%	92.62%
CHEMBL2581	P07339	Cathepsin D	83.64%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.75%	96.77%
CHEMBL255	P29275	Adenosine A2b receptor	81.14%	98.59%
CHEMBL2664	P23526	Adenosylhomocysteinase	81.12%	86.67%
CHEMBL4072	P07858	Cathepsin B	80.22%	93.67%

Plants that contains it

• Arabidopsis thaliana
• Artemisia absinthium
• Elsholtzia ciliata
• Jasminum sambac
• Mosla chinensis

Cross-Links

• PubChem: 5281929
• NPASS: NPC154728
• LOTUS: LTS0211526
• wikiData: Q26840883