N-(9-Ethoxy-1,8-dihydroxy-12a-methyl-1,2,3,3a,3b,4,5,6,10b,11,12,12a-dodecahydro-benzo[3,4]cyclohepta[1,2-e]inden-6-yl)-acetamide

ID: ALA79445

PubChem CID: 10620255

Max Phase: Preclinical

Molecular Formula: C23H33NO4

Molecular Weight: 387.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc2c(cc1O)[C@H](NC(C)=O)CC[C@H]1C3CC[C@H](O)[C@@]3(C)CC[C@H]21

Standard InChI:  InChI=1S/C23H33NO4/c1-4-28-21-12-16-14-9-10-23(3)18(6-8-22(23)27)15(14)5-7-19(24-13(2)25)17(16)11-20(21)26/h11-12,14-15,18-19,22,26-27H,4-10H2,1-3H3,(H,24,25)/t14-,15+,18?,19+,22-,23-/m0/s1

Standard InChI Key:  YRMUBJUOYFERGW-IGDFVKFMSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  1  0  0  0  0  0999 V2000
    2.2292   -2.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3792   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -2.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1917   -2.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8000   -1.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -4.0042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4125   -1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -3.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1917   -2.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1667   -1.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8250   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8542   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1792   -3.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -5.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -3.3875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2250   -0.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -2.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0042   -0.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6750   -1.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7917   -2.2292    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -1.7167    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2 10  1  0
  3  1  1  0
  4  1  1  0
  5  6  1  0
  6  4  1  0
  7  1  2  0
  8  3  2  0
  9  3  1  0
 10 12  1  0
  9 11  1  1
 12  4  1  0
 13 14  2  0
 14  7  1  0
 15  6  1  0
 16  5  1  0
 17 11  1  0
 18  2  1  0
 19  9  1  0
 20 16  1  0
 21 17  2  0
 22 13  1  0
  2 23  1  1
 24 14  1  0
 18 25  1  1
 26 17  1  0
 27 24  1  0
 28 27  1  0
  6 29  1  1
  4 30  1  6
  8 13  1  0
  5  2  1  0
 15 19  1  0
 18 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA79445

   N-[(1S,8R,11R,15S,16S)-4-ethoxy-5,15-dihydroxy-16-methyl-8-tetracyclo[9.7.0.02,7.012,16]octadeca-2,4,6-trienyl]acetamide

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: 387.52

Molecular Weight (Monoisotopic): 387.2410

AlogP: 4.03

#Rotatable Bonds: 3

Polar Surface Area: 78.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.10

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: 2.87

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.73

Np Likeness Score: 1.43

References

1. Wang Z, Yang D, Mohanakrishnan AK, Fanwick PE, Nampoothiri P, Hamel E, Cushman M..  (2000)  Synthesis of B-ring homologated estradiol analogues that modulate tubulin polymerization and microtubule stability.,  43  (12): [PMID:10882369] [10.1021/jm0001119]

Source

Source(1):

• Scientific Literature