(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 diethylamide

ID: ALA3706583

PubChem CID: 44315759

Max Phase: Preclinical

Molecular Formula: C23H34N2O2

Molecular Weight: 370.54

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C23H34N2O2/c1-5-25(6-2)21(27)19-8-7-17-16-14-24-20-13-15(26)9-11-23(20,4)18(16)10-12-22(17,19)3/h9,11,13,16-19,24H,5-8,10,12,14H2,1-4H3/t16?,17?,18?,19-,22+,23-/m1/s1

Standard InChI Key:  JMOVVUIUYILSOJ-PAJIOFOTSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  1  0  0  0  0  0999 V2000
    0.3295   -1.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222   -2.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8222   -3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1176   -0.7923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253   -1.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -1.8432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3803   -0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -2.2685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1092   -3.4945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353   -1.8389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5353   -3.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3753   -0.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3961   -3.0899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0967   -1.0175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1051   -2.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -1.4637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484   -2.2560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2484   -3.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    0.1501    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8299    0.6088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614   -3.4945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3253   -0.2627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640   -1.5054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4561    0.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7314   -0.4671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5445   -0.3044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2651    1.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  2  1  0
  4  1  1  0
  5  1  1  0
  6 14  1  0
  4  7  1  1
  8  5  1  0
  9 13  1  0
 10  2  1  0
 11  3  2  0
 12  1  1  0
 13  8  1  0
 14 12  1  0
 15  5  1  0
 16  4  1  0
 17 10  2  0
 18 17  1  0
 19  7  1  0
 20  7  2  0
 21 18  2  0
  1 22  1  1
  2 23  1  1
 24 19  1  0
 25 19  1  0
 26 25  1  0
 27 24  1  0
  6  8  1  0
 15 16  1  0
  3  9  1  0
 11 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706583

   (1S,9aR,11aS)-N,N-diethyl-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: 3.55

#Rotatable Bonds: 3

Polar Surface Area: 49.41

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.49

CX LogP: 2.68

CX LogD: 2.68

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.83

Np Likeness Score: 1.23

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