Methyl cucurbate

ID: ALA2272535

PubChem CID: 11009664

Max Phase: Preclinical

Molecular Formula: C13H22O3

Molecular Weight: 226.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC/C=C\C[C@H]1[C@@H](CC(=O)OC)CC[C@@H]1O

Standard InChI:  InChI=1S/C13H22O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-12,14H,3,6-9H2,1-2H3/b5-4-/t10-,11+,12+/m1/s1

Standard InChI Key:  OOYCGMQJIWHWHA-YYEJGFRBSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   18.2877   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1049   -2.5919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3593   -1.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6963   -1.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0376   -1.8152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6951   -0.5159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1368   -1.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5845   -3.2536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2512   -3.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4384   -4.0842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7308   -4.6614    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7434   -2.1114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5209   -1.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6919   -1.0609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4695   -0.8094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5436   -4.5770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  4  6  1  6
  3  7  1  1
  2  8  1  1
  8  9  1  0
  9 10  2  0
  9 11  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 11 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2272535

   METHYL CUCURBATE

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 226.32

Molecular Weight (Monoisotopic): 226.1569

AlogP: 2.29

#Rotatable Bonds: 5

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.17

CX LogD: 2.17

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.58

Np Likeness Score: 2.10

References

1. Seto H, Nomura E, Fujioka S, Koshino H, Suenaga T, Yoshida S..  (1999)  Easy Preparation of Methyl 7-epi-Jasmonate and Four Stereoisomers of Methyl Cucurbate, and Assessment of the Stereogenic Effect of Jasmonate on Phytohormonal Activities.,  63  (2): [PMID:27393062] [10.1271/bbb.63.361]

Source

Source(1):

• Scientific Literature