(10R,13S)-10,13-Dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

ID: ALA2311155

PubChem CID: 71716701

Max Phase: Preclinical

Molecular Formula: C19H26O2

Molecular Weight: 286.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [3H]C1CC2=CC(=O)CC[C@]2(C)[C@H]2CC[C@]3(C)C(=O)CC[C@H]3[C@H]12

Standard InChI:  InChI=1S/C19H26O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1/i4T/t4?,14-,15-,16-,18-,19-

Standard InChI Key:  AEMFNILZOJDQLW-GAFYTTOSSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -1.4990    0.6271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9671   -0.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1253    0.9175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9374    1.0627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4692    0.4320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1889   -0.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8403   -0.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5231   -0.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2938    0.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8291    1.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868    0.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3111    0.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914   -0.2940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -0.9248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2474   -0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7156   -1.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0965   -1.2650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3768   -0.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1550    0.1416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035   -0.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8001    1.0566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6283   -1.8957    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7996    0.9061    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0214   -1.2536    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9494   -1.3148    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1 12  1  0
  2 11  1  1
  2 15  1  0
  2 19  1  0
  3  4  1  0
 19  3  1  0
  4  5  1  0
  5  6  1  0
  5  9  1  0
  5 10  1  1
  6  7  1  0
  6 18  1  0
  7  8  1  0
  8  9  1  0
  9 21  2  0
 12 13  1  0
 13 14  1  0
 13 20  2  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 18 17  1  0
 18 19  1  0
 17 22  1  0
 19 23  1  6
 18 24  1  1
  6 25  1  6
M  ISO  1  22   3
M  END

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: 286.42

Molecular Weight (Monoisotopic): 286.1933

AlogP: 4.09

#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: 3.93

CX LogD: 3.93

Aromatic Rings: ┄

Heavy Atoms: 21

QED Weighted: 0.67

Np Likeness Score: 2.14

References

1. Li X, Singh SM, Côté J, Laplante S, Veilleux R, Labrie F..  (1995)  Synthesis and in vitro evaluation of 4-substituted N-(1,1-dimethylethyl)-3-oxo-4-androstene-17 beta-carboxamides as 5 alpha-reductase inhibitors and antiandrogens.,  38  (9): [PMID:7739004] [10.1021/jm00009a006]

Source

Source(1):

• Scientific Literature