4-Hydroxy-10,13-dimethyl-9,10,11,12,13,14,15,16-octahydro-8H-cyclopenta[a]phenanthrene-3,17-dione

ID: ALA166635

PubChem CID: 44379060

Max Phase: Preclinical

Molecular Formula: C19H22O3

Molecular Weight: 298.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12C=CC(=O)C(O)=C1C=CC1C2CCC2(C)C(=O)CCC12

Standard InChI:  InChI=1S/C19H22O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h3-4,8,10-13,22H,5-7,9H2,1-2H3

Standard InChI Key:  NMSKTPUZMBOAGF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
    2.1292   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2917   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -7.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8417   -7.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5625   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5792   -4.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -5.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0667   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5542   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208   -7.8042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -4.3042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125   -8.6250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1250   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2875   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 14  1  0
  4  1  1  0
  5  2  2  0
  6  4  1  0
  7  6  1  0
  8  2  1  0
  9  1  1  0
 10  6  1  0
 11 12  1  0
 12  9  2  0
 13  3  1  0
 14 15  1  0
 15  4  1  0
 16  7  1  0
 17 16  1  0
 18 11  2  0
 19 13  2  0
 20  5  1  0
 21  1  1  0
 22  3  1  0
  5 11  1  0
  8 10  2  0
  7  3  1  0
 17 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA166635

   4-hydroxy-10,13-dimethyl-9,11,12,14,15,16-hexahydro-8H-cyclopenta[a]phenanthrene-3,17-dione

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: 298.38

Molecular Weight (Monoisotopic): 298.1569

AlogP: 3.53

#Rotatable Bonds: ┄

Polar Surface Area: 54.37

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.94

CX Basic pKa: ┄

CX LogP: 3.05

CX LogD: 3.04

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.74

Np Likeness Score: 2.54

References

1. Marsh DA, Brodie HJ, Garrett W, Tsai-Morris CH, Brodie AM..  (1985)  Aromatase inhibitors. Synthesis and biological activity of androstenedione derivatives.,  28  (6): [PMID:4009601] [10.1021/jm00383a017]

Source

Source(1):

• Scientific Literature