(1S,9aR,11aS)-9a,11a-Dimethyl-7-oxo-2,3,3a,3b,4,5,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid tert-butylamide

ID: ALA3706586

PubChem CID: 44316063

Max Phase: Preclinical

Molecular Formula: C23H34N2O2

Molecular Weight: 370.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)NC(=O)[C@H]1CCC2C3CNC4=CC(=O)C=C[C@]4(C)C3CC[C@@]21C

Standard InChI:  InChI=1S/C23H34N2O2/c1-21(2,3)25-20(27)18-7-6-16-15-13-24-19-12-14(26)8-10-23(19,5)17(15)9-11-22(16,18)4/h8,10,12,15-18,24H,6-7,9,11,13H2,1-5H3,(H,25,27)/t15?,16?,17?,18-,22+,23-/m1/s1

Standard InChI Key:  WULOIBNYBPVLMK-UBCBZESQSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    5.8174   -4.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9738   -3.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8091   -5.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9655   -4.5177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5320   -4.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2383   -4.9272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0187   -2.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7554   -3.4478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5237   -6.1601    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -4.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1028   -6.1559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8336   -2.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2634   -3.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2467   -5.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5362   -3.6777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7428   -4.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2318   -4.1165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923   -4.9189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3923   -5.7464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4753   -2.0436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3810   -3.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6735   -6.1601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9655   -2.9129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7715   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   -3.9034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1876   -2.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6413   -3.4896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2 13  1  0
  3  1  1  0
  4  6  1  0
  5  1  1  0
  6  5  1  0
  8  7  1  1
  8  2  1  0
  9  3  1  0
 10  1  1  0
 11  3  2  0
 12  7  1  0
 13 15  1  0
 14  6  1  0
 15  5  1  0
 16  4  1  0
 17 16  1  0
 18 10  2  0
 19 18  1  0
 20  7  2  0
 21 12  1  0
 22 19  2  0
  2 23  1  1
  1 24  1  1
 25 21  1  0
 26 21  1  0
 27 21  1  0
 11 19  1  0
  9 14  1  0
  2  4  1  0
 17  8  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706586

   (1S,9aR,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,9b,10,11-decahydrocyclopenta[i]phenanthridine-1-carboxamide

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: 370.54

Molecular Weight (Monoisotopic): 370.2620

AlogP: 3.59

#Rotatable Bonds: 1

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.16

CX LogP: 2.79

CX LogD: 2.79

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.74

Np Likeness Score: 1.46

References

1. Frye SV, Haffner CD, Maloney PR, Mook RA, Dorsey GF, Hiner RN, Cribbs CM, Wheeler TN, Ray JA, Andrews RC..  (1994)  6-Azasteroids: structure-activity relationships for inhibition of type 1 and 2 human 5 alpha-reductase and human adrenal 3 beta-hydroxy-delta 5-steroid dehydrogenase/3-keto-delta 5-steroid isomerase.,  37  (15): [PMID:8057283] [10.1021/jm00041a014]

Source

Source(1):

• Scientific Literature