(8S,9S,10R,13S,14S)-6,10,13-trimethyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

ID: ALA3986794

PubChem CID: 68087404

Max Phase: Preclinical

Molecular Formula: C25H31NO

Molecular Weight: 361.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1C[C@@H]2[C@H](CC[C@]3(C)C(c4cccnc4)CC[C@@H]23)[C@@]2(C)C=CC(=O)C=C12

Standard InChI:  InChI=1S/C25H31NO/c1-16-13-19-21-7-6-20(17-5-4-12-26-15-17)24(21,2)11-9-22(19)25(3)10-8-18(27)14-23(16)25/h4-5,8,10,12,14-16,19-22H,6-7,9,11,13H2,1-3H3/t16?,19-,20?,21-,22-,24+,25+/m0/s1

Standard InChI Key:  AGZOZNZGJNVQON-PGMULWQHSA-N

Molfile:  

     RDKit          2D

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    7.1484   -7.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393   -6.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0393   -6.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7446   -7.2846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7446   -5.6502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4499   -6.0629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4464   -6.8801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8585   -6.8861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1554   -5.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5687   -5.6709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3399   -5.9308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.6152   -3.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3322   -7.2897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4163   -3.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6774   -2.9065    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1369   -2.2923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3322   -2.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0749   -3.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1484   -6.4715    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4426   -5.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8500   -5.2540    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5723   -4.0364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1437   -8.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5640   -6.4880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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 17 13  1  0
 17 18  1  0
  3 19  2  0
 18 20  2  0
 20 21  1  0
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 24 18  1  0
  9 25  1  6
  6 26  1  1
 10 27  1  1
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  1 29  1  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3986794

   (8S,9S,10R,13S,14S)-6,10,13-trimethyl-17-pyridin-3-yl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-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: 361.53

Molecular Weight (Monoisotopic): 361.2406

AlogP: 5.72

#Rotatable Bonds: 1

Polar Surface Area: 29.96

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.47

CX LogP: 5.08

CX LogD: 5.08

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.64

Np Likeness Score: 1.91

References

1.  (2013)  C-17-heteroaryl steroidal compounds as inhibitors of CYP11B, CYP17, and/or CYP21, 

Source

Source(1):

• Patent Bioactivity Data