3-((5S,8R,9S,10S,13S,14S)-3-methoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)pyridine

ID: ALA3974234

PubChem CID: 89883040

Max Phase: Preclinical

Molecular Formula: C25H35NO

Molecular Weight: 365.56

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1CC[C@@]2(C)[C@@H](CC[C@@H]3[C@@H]2CC[C@]2(C)C(c4cccnc4)=CC[C@@H]32)C1

Standard InChI:  InChI=1S/C25H35NO/c1-24-12-10-19(27-3)15-18(24)6-7-20-22-9-8-21(17-5-4-14-26-16-17)25(22,2)13-11-23(20)24/h4-5,8,14,16,18-20,22-23H,6-7,9-13,15H2,1-3H3/t18-,19?,20-,22-,23-,24-,25+/m0/s1

Standard InChI Key:  NFEGCGGXCXXPQW-SUHYMMFHSA-N

Molfile:  

     RDKit          2D

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    1.8673    0.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3440   -0.2958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.9573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3377   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3857   -2.3228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952   -1.9033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5089   -1.0573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7909   -0.6589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -1.0783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0793    0.1273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0793    0.9524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3580   -1.4977    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0814   -0.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2420   -2.2839    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9462   -1.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0952   -2.7284    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474   -0.2712    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.5187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5869    1.7747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8548    2.5497    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6620    2.7118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2029    2.0926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 13 12  1  0
 13 14  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
  2 18  1  0
  5 18  1  0
 18 19  1  1
  6 15  1  0
 15 20  1  6
  9 14  1  0
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 11 22  1  0
 22 23  1  0
  9 24  1  6
  6 25  1  1
  5 26  1  6
 27  1  2  0
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 29 28  2  0
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 31 30  2  0
  1 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974234

   3-[(5S,8R,9S,10S,13S,14S)-3-methoxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]pyridine

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: 365.56

Molecular Weight (Monoisotopic): 365.2719

AlogP: 6.13

#Rotatable Bonds: 2

Polar Surface Area: 22.12

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 2

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.81

CX LogP: 5.01

CX LogD: 5.01

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.63

Np Likeness Score: 1.77

References

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

2. Blass, Benjamin E BE and 18 more authors.  2016-12-01  Design, synthesis, and evaluation of (2S,4R)-Ketoconazole sulfonamide analogs as potential treatments for Metabolic Syndrome.  [PMID:27789139]

3. Fehl, Charlie C and 5 more authors.  2018-06-14  Structure-Based Design of Inhibitors with Improved Selectivity for Steroidogenic Cytochrome P450 17A1 over Cytochrome P450 21A2.  [PMID:29792703]

Source

Source(1):

• Patent Bioactivity Data