methyl-6-epi-cucurbate

ID: ALA2272536

PubChem CID: 11107054

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-DKLPLTIYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   24.1484   -2.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9656   -2.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2199   -1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5570   -1.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8982   -1.8070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5557   -0.5077    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9975   -1.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4451   -3.2454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1119   -3.9915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2991   -4.0760    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5914   -4.6532    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.6040   -2.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3816   -1.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5526   -1.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3301   -0.8012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4043   -4.5687    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  1
  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:

   

   ALA2272536

   METHYL-6-EPI-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