(8S,9S,10R,13S,14S)-10,13-dimethyl-17-(pyridin-3-yl)-7,8,9,11,12,13,14,15-octahydrospiro[cyclopenta[a]phenanthrene-6,1'-cyclopropan]-3(10H)-one

ID: ALA3974457

PubChem CID: 68087249

Max Phase: Preclinical

Molecular Formula: C26H29NO

Molecular Weight: 371.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C=CC(=O)C=C1C1(CC1)C[C@@H]1[C@@H]2CC[C@]2(C)C(c3cccnc3)=CC[C@@H]12

Standard InChI:  InChI=1S/C26H29NO/c1-24-10-8-22-19(21(24)6-5-20(24)17-4-3-13-27-16-17)15-26(11-12-26)23-14-18(28)7-9-25(22,23)2/h3-5,7,9,13-14,16,19,21-22H,6,8,10-12,15H2,1-2H3/t19-,21-,22-,24+,25+/m0/s1

Standard InChI Key:  TWCKCVMGTLFGIN-WRUJZFPBSA-N

Molfile:  

     RDKit          2D

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    9.6577  -12.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2532  -11.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8443  -12.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8206   -9.9600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1133  -10.3783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1177  -11.1974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8334  -11.6023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5407  -11.1881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9636  -11.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9552  -10.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6666   -9.9415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4426  -10.1835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9114   -9.5282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4253   -8.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6581   -9.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9465   -8.7133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2392   -9.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2436   -9.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5363  -10.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5278   -9.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2436  -10.7740    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7527   -8.3073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6926   -8.0720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1248   -7.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3921   -6.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1766   -6.5157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7191   -7.1164    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4771   -7.8966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6666  -10.7647    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9552   -9.5365    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4128  -11.6109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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 16 17  1  0
 17 18  1  0
 10 18  1  0
 18 19  1  0
  8 19  1  0
  4 19  1  0
 19 20  1  1
 18 21  1  6
 15 22  1  1
 14 23  1  0
 24 23  1  0
 24 25  2  0
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  6 31  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3974457

   (8S,9S,10R,13S,14S)-10,13-dimethyl-17-pyridin-3-ylspiro[8,9,11,12,14,15-hexahydro-7H-cyclopenta[a]phenanthrene-6,1'-cyclopropane]-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: 371.52

Molecular Weight (Monoisotopic): 371.2249

AlogP: 5.77

#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: 4.81

CX LogP: 4.65

CX LogD: 4.65

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 1.76

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