1-(R)-Ethyl-3-((9S,10S,14S,16R)-17-(S)-imidazol-1-yl-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl)-urea

ID: ALA3925707

PubChem CID: 89817179

Max Phase: Preclinical

Molecular Formula: C25H38N4O

Molecular Weight: 410.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)N[C@@H]1CC[C@@]2(C)C(CC[C@@H]3[C@@H]2CC[C@]2(C)C(n4ccnc4)=CC[C@@H]32)C1

Standard InChI:  InChI=1S/C25H38N4O/c1-4-27-23(30)28-18-9-11-24(2)17(15-18)5-6-19-20-7-8-22(29-14-13-26-16-29)25(20,3)12-10-21(19)24/h8,13-14,16-21H,4-7,9-12,15H2,1-3H3,(H2,27,28,30)/t17?,18-,19+,20+,21+,24+,25+/m1/s1

Standard InChI Key:  CUYBGUWAAACGAV-BVJRKNLISA-N

Molfile:  

     RDKit          2D

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   34.5111  -11.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8018  -11.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9298  -11.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3549  -11.0336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9351  -10.1973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2203  -11.4306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1410   -9.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3473  -11.8493    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   38.4034   -9.1908    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.1265  -11.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.0956  -12.6636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   35.9227  -11.8373    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.6282  -10.6171    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   33.8018  -12.2524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6712  -12.6699    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.5111  -12.6550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   30.2558  -12.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6533   -9.7993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9228  -12.6599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6364  -11.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3759  -12.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3712  -11.4391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.9605  -12.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2130  -10.6088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6368  -12.2584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3599  -10.2139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1429   -9.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1873   -8.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1949   -8.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4120   -7.8567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.9206   -8.5202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7 28  1  0
 28 29  1  1
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  4  8  1  6
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  6  1  1  0
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  6 12  1  0
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  7  9  1  0
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  4 10  1  0
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  3 13  1  6
  6  3  1  0
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  2 15  1  0
 11 23  1  0
 17 12  1  0
 23 24  2  0
 28  4  1  0
  9 30  1  0
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 32 33  2  0
 33  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3925707

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

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: 410.61

Molecular Weight (Monoisotopic): 410.3046

AlogP: 5.06

#Rotatable Bonds: 3

Polar Surface Area: 58.95

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.12

CX LogP: 3.43

CX LogD: 3.41

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.73

Np Likeness Score: 0.51

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