Benzoic acid 10,13-dimethyl-3,17-dioxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-4-yl ester

ID: ALA167676

PubChem CID: 44379108

Max Phase: Preclinical

Molecular Formula: C26H28O4

Molecular Weight: 404.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC12CCC3C(C=CC4=C(OC(=O)c5ccccc5)C(=O)CCC43C)C1CCC2=O

Standard InChI:  InChI=1S/C26H28O4/c1-25-15-13-21(27)23(30-24(29)16-6-4-3-5-7-16)20(25)9-8-17-18-10-11-22(28)26(18,2)14-12-19(17)25/h3-9,17-19H,10-15H2,1-2H3

Standard InChI Key:  JFHSFIQPXPMSFO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 34  0  0  0  0  0  0  0  0999 V2000
    2.1250   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292   -6.5625    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
    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
    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
    1.4125   -8.6250    0.0000 O   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
    3.5625   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -9.0292    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
    5.0792   -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
    1.4125   -6.1417    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
   -0.0208   -8.6167    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
    5.5542   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000   -9.8542    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
    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
   -0.0208  -10.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4125  -10.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4167  -11.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0208  -11.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000  -11.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  2  0
  4  7  1  0
  5  2  1  0
  6 10  1  0
  7  6  1  0
  8  3  1  0
  9  1  1  0
 10  9  2  0
 11  8  1  0
 12  3  1  0
 13  4  1  0
 14 16  1  0
 15  2  1  0
 16  5  1  0
 17  7  1  0
 18 11  2  0
 19 12  1  0
 20 17  1  0
 21 11  1  0
 22 12  2  0
 23 13  2  0
 24  2  1  0
 25  4  1  0
 26 21  2  0
 27 21  1  0
 28 27  2  0
 29 26  1  0
 30 28  1  0
  5  6  1  0
 15 19  1  0
 14  4  1  0
 20 13  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA167676

   (10,13-dimethyl-3,17-dioxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-4-yl) benzoate

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: 404.51

Molecular Weight (Monoisotopic): 404.1988

AlogP: 5.05

#Rotatable Bonds: 2

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: 1.54

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