Natural Product: ENC001581

NPs Basic Information

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Name
Methyl jasmonate
Molecular Formula C13H20O3
IUPAC Name*
methyl 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate
SMILES
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
InChIKey
GEWDNTWNSAZUDX-WQMVXFAESA-N
Synonyms
Methyl jasmonate; 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 jasmonic acid; CHEBI:15929; Methyl (2-pent-2-enyl-3-oxo-1-cyclopentyl)acetate; 3-oxo-2-(2-pentenyl)cyclopentaneacetic acid methyl ester; methyl 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetate; Z-Methyl jasmonoate; 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 (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)))-; Methyl dl-jasmonate; Cyclopentaneacetic acid, 3-oxo-trans-2-(cis-2-pentenyl), methyl ester; Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate; 39924-52-2; FEMA No. 3410; UNII-900N171A0F; HSDB 8131; 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)))-; EINECS 214-918-6; EINECS 243-497-1; SCHEMBL36186; METHYL JASMONATE [FHFI]; CHEMBL2139332; DTXSID3036731; FEMA 3410; (3R,7R)-(?)-Methyl jasmonate; Methyl 3-oxo-2-(2-pentenyl)cyclopentaneacetate, (Z)-trans-; CMC_7389; ZINC4654657; BDBM50509748; CMC_13964; LMFA02020010; (+-)-Cyclopentaneacetic acid, 3-oxo-trans-2-(cis-2-pentenyl), methyl ester; AKOS015950850; JASMONIC ACID METHYL ESTER [MI]; AS-75742; HY-135663; CS-0113712; D94878; A891945; Q26840883; 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)-; 139442-00-5
CAS 1211-29-6
PubChem CID 5281929
ChEMBL ID CHEMBL2139332
*Note: the IUPAC Name was collected from PubChem.
Chemical Classification:
  • Kingdom: Organic compounds
    • Superclass: Lipids and lipid-like mol
      • Class: Fatty Acyls
        • Subclass: Lineolic acids and deriva
          • Direct Parent: Jasmonic acids

ClassyFire Version 1.0
PMID:27867422

NPs Species Source

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NPs Physi-Chem Properties

Molecular Weight: 224.3 ALogp: 1.9
HBD: 0 HBA: 3
Rotatable Bonds: 6 Lipinski's rule of five: Accepted
Polar Surface Area: 43.4 Aromatic Rings: 1
Heavy Atoms: 16 QED Weighted: 0.531

NPs ADMET Properties*

ADMET: Absorption

Caco-2 Permeability: -4.576 MDCK Permeability: 0.00004840
Pgp-inhibitor: 0.059 Pgp-substrate: 0.003
Human Intestinal Absorption (HIA): 0.013 20% Bioavailability (F20%): 0.899
30% Bioavailability (F30%): 0.975

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB): 0.966 Plasma Protein Binding (PPB): 66.70%
Volume Distribution (VD): 0.36 Fu: 34.84%

ADMET: Metabolism

CYP1A2-inhibitor: 0.091 CYP1A2-substrate: 0.553
CYP2C19-inhibitor: 0.211 CYP2C19-substrate: 0.858
CYP2C9-inhibitor: 0.105 CYP2C9-substrate: 0.636
CYP2D6-inhibitor: 0.006 CYP2D6-substrate: 0.859
CYP3A4-inhibitor: 0.133 CYP3A4-substrate: 0.323

ADMET: Excretion

Clearance (CL): 9.458 Half-life (T1/2): 0.941

ADMET: Toxicity

hERG Blockers: 0.011 Human Hepatotoxicity (H-HT): 0.425
Drug-inuced Liver Injury (DILI): 0.258 AMES Toxicity: 0.027
Rat Oral Acute Toxicity: 0.139 Maximum Recommended Daily Dose: 0.724
Skin Sensitization: 0.137 Carcinogencity: 0.799
Eye Corrosion: 0.176 Eye Irritation: 0.388
Respiratory Toxicity: 0.07
*Note: the ADMET properties was calculated by ADMETlab 2.0. Reference: PMID: 33893803.

Similar Compounds*

Compounds similar to EMNPD with top10 similarity:

*Note: the compound similarity was calculated by RDKIT.