9-Ethoxy-1,8-dihydroxy-12a-methyl-2,3,3a,3b,4,5,10b,11,12,12a-decahydro-1H-benzo[3,4]cyclohepta[1,2-e]inden-6-one

ID: ALA432546

PubChem CID: 10593564

Max Phase: Preclinical

Molecular Formula: C21H28O4

Molecular Weight: 344.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOc1cc2c(cc1O)C(=O)CCC1C2CC[C@@]2(C)C1CC[C@@H]2O

Standard InChI:  InChI=1S/C21H28O4/c1-3-25-19-11-14-12-8-9-21(2)16(5-7-20(21)24)13(12)4-6-17(22)15(14)10-18(19)23/h10-13,16,20,23-24H,3-9H2,1-2H3/t12?,13?,16?,20-,21-/m0/s1

Standard InChI Key:  MWMQARHZUCGXAL-HIZMWCFTSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  1  0  0  0  0  0999 V2000
    1.4667   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -1.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417   -2.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -1.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8375   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -3.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4042   -1.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -2.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0917   -0.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542   -3.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -3.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4625   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -2.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417   -0.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875   -1.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6083   -1.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  9  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 11  1  0
 10  3  1  0
 11  4  1  0
 12 13  2  0
 13  7  1  0
 14  5  1  0
 15  6  1  0
 16  2  1  0
 17 10  1  0
 18 14  1  0
 19 10  2  0
 20 12  1  0
  2 21  1  1
 22 13  1  0
 16 23  1  1
 24 22  1  0
 25 24  1  0
  8 12  1  0
  5  2  1  0
 15 17  1  0
 16 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA432546

   (15S,16S)-4-ethoxy-5,15-dihydroxy-16-methyltetracyclo[9.7.0.02,7.012,16]octadeca-2,4,6-trien-8-one

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: 344.45

Molecular Weight (Monoisotopic): 344.1988

AlogP: 4.04

#Rotatable Bonds: 2

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.69

CX Basic pKa: ┄

CX LogP: 3.24

CX LogD: 3.24

Aromatic Rings: 1

Heavy Atoms: 25

QED Weighted: 0.85

Np Likeness Score: 1.86

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