(6R,9S)-9,10-dihydroxy-4-megastigmen-3-one

ID: ALA2331818

PubChem CID: 23583100

Max Phase: Preclinical

Molecular Formula: C13H22O3

Molecular Weight: 226.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=CC(=O)CC(C)(C)[C@H]1CC[C@H](O)CO

Standard InChI:  InChI=1S/C13H22O3/c1-9-6-11(16)7-13(2,3)12(9)5-4-10(15)8-14/h6,10,12,14-15H,4-5,7-8H2,1-3H3/t10-,12-/m0/s1

Standard InChI Key:  RZMRKQQJGBTKOK-JQWIXIFHSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
    6.5623   -5.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5623   -6.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2676   -6.6655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9729   -6.2610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9729   -5.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2676   -5.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8552   -6.6706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6800   -6.6706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6820   -4.4492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6684   -4.3212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6818   -5.0373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3883   -5.4480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0972   -5.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8037   -5.4521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5126   -5.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0996   -4.2243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  2  7  2  0
  4  8  1  0
  6  9  1  0
  6 10  1  0
  5 11  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA2331818

   (4R)-4-[(3S)-3,4-dihydroxybutyl]-3,5,5-trimethylcyclohex-2-en-1-one

Molecule Features

Natural Product: Yes

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: 1.68

#Rotatable Bonds: 4

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.77

Np Likeness Score: 2.63

References

1. Pan L, Acuña UM, Li J, Jena N, Ninh TN, Pannell CM, Chai H, Fuchs JR, Carcache de Blanco EJ, Soejarto DD, Kinghorn AD..  (2013)  Bioactive flavaglines and other constituents isolated from Aglaia perviridis.,  76  (3): [PMID:23301897] [10.1021/np3007588]

Source

Source(1):

• Scientific Literature