(8R,9S,10R,13S,14S,E)-4,10,13-trimethyl-17-(pyridin-3-yl)-6,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one oxime

ID: ALA3968557

PubChem CID: 88584420

Max Phase: Preclinical

Molecular Formula: C25H32N2O

Molecular Weight: 376.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C2CC[C@@H]3[C@H](CC[C@]4(C)C(c5cccnc5)=CC[C@@H]34)[C@@]2(C)CC/C1=N\O

Standard InChI:  InChI=1S/C25H32N2O/c1-16-19-7-6-18-21-9-8-20(17-5-4-14-26-15-17)25(21,3)12-10-22(18)24(19,2)13-11-23(16)27-28/h4-5,8,14-15,18,21-22,28H,6-7,9-13H2,1-3H3/b27-23+/t18-,21-,22-,24-,25+/m0/s1

Standard InChI Key:  SMGPYVBOEYPOST-UMXDAQROSA-N

Molfile:  

     RDKit          2D

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    7.1597  -10.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4998   -8.9173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3039  -10.8443    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8228   -8.3615    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7688   -8.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1973   -7.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4664   -6.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2560   -6.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8020   -7.1628    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.5585   -7.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7362  -10.8349    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.0201   -9.5987    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8888  -12.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4522  -11.6872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7360  -11.2797    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5 17  1  0
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 16 19  1  6
 13 20  1  1
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M  END

Alternative Forms

1. Parent:

   

   ALA3968557

   (NE)-N-[(8R,9S,10R,13S,14S)-4,10,13-trimethyl-17-pyridin-3-yl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-ylidene]hydroxylamine

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: 376.54

Molecular Weight (Monoisotopic): 376.2515

AlogP: 6.26

#Rotatable Bonds: 1

Polar Surface Area: 45.48

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.51

CX Basic pKa: 4.82

CX LogP: 4.94

CX LogD: 4.94

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: 1.52

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