6-Bromo-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

ID: ALA351449

PubChem CID: 44378959

Max Phase: Preclinical

Molecular Formula: C19H25BrO2

Molecular Weight: 365.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCC3C(C[C@H](Br)C4=CC(=O)CCC43C)C1CCC2=O

Standard InChI:  InChI=1S/C19H25BrO2/c1-18-7-5-11(21)9-15(18)16(20)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16H,3-8,10H2,1-2H3/t12?,13?,14?,16-,18?,19?/m0/s1

Standard InChI Key:  HAWQRBIGKRAICT-GXXLBWDJSA-N

Molfile:  

     RDKit          2D

 22 25  0  0  1  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
    3.5542   -6.5667    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
    4.2792   -6.1625    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
    2.8417   -7.8042    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
    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
    1.4125   -6.1417    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
    0.7042   -7.3917    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
    5.3417   -4.3042    0.0000 O   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
    0.7042   -6.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8292   -8.6292    0.0000 Br  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  5  1  0
  4 11  1  0
  5  1  1  0
  6  3  1  0
  7  3  1  0
  8  2  1  0
  9  2  2  0
 10  4  1  0
 11 12  1  0
 12  5  1  0
 13  1  1  0
 14  6  1  0
 15 19  1  0
 16 14  1  0
 17 10  2  0
 18 15  2  0
 19 13  1  0
  8 20  1  6
 21  1  1  0
 22  4  1  0
  8  7  1  0
 15  9  1  0
  6  4  1  0
 16 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA351449

   (6S)-6-bromo-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-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: 365.31

Molecular Weight (Monoisotopic): 364.1038

AlogP: 4.46

#Rotatable Bonds: ┄

Polar Surface Area: 34.14

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.24

CX LogD: 4.24

Aromatic Rings: ┄

Heavy Atoms: 22

QED Weighted: 0.59

Np Likeness Score: 2.11

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