(3S,8R,9S,10R,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,7,8,9,10,11,12,13-decahydro-1H-cyclopenta[a]phenanthren-3-ylpivalate

ID: ALA3933057

PubChem CID: 68087215

Max Phase: Preclinical

Molecular Formula: C29H37NO2

Molecular Weight: 431.62

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)O[C@H]1CC[C@@]2(C)C(=CC[C@H]3C4=CC=C(c5cccnc5)[C@@]4(C)CC[C@@H]32)C1

Standard InChI:  InChI=1S/C29H37NO2/c1-27(2,3)26(31)32-21-12-14-28(4)20(17-21)8-9-22-24-11-10-23(19-7-6-16-30-18-19)29(24,5)15-13-25(22)28/h6-8,10-11,16,18,21-22,25H,9,12-15,17H2,1-5H3/t21-,22-,25-,28-,29+/m0/s1

Standard InChI Key:  OFTDZEXIUMFCGY-XSZZMTPHSA-N

Molfile:  

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   35.5366   -5.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

1. Parent:

   

   ALA3933057

   [(3S,8R,9S,10R,13S)-10,13-dimethyl-17-pyridin-3-yl-2,3,4,7,8,9,11,12-octahydro-1H-cyclopenta[a]phenanthren-3-yl] 2,2-dimethylpropanoate

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: 431.62

Molecular Weight (Monoisotopic): 431.2824

AlogP: 6.92

#Rotatable Bonds: 2

Polar Surface Area: 39.19

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 4.77

CX LogP: 5.80

CX LogD: 5.80

Aromatic Rings: 1

Heavy Atoms: 32

QED Weighted: 0.38

Np Likeness Score: 1.57

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