methyl-7-epi-cucurbate

ID: ALA2272537

PubChem CID: 11195486

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-UMOJZNBSSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    1.4404   -9.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2576   -9.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5119   -8.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8490   -7.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1902   -8.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477   -7.0245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2895   -8.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7371   -9.7623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4039  -10.5084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5911  -10.5929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8834  -11.1701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8960   -8.6201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6736   -8.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -7.5695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6221   -7.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6962  -11.0856    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  6
  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:

   

   ALA2272537

   METHYL-7-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