(1S,9aR,11aS)-6,9a,11a-Trimethyl-7-oxo-2,3,3a,3b,4,5,7,9a,9b,10,11,11a-dodecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid diethylamide

ID: ALA3706585

PubChem CID: 44316042

Max Phase: Preclinical

Molecular Formula: C24H36N2O2

Molecular Weight: 384.56

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C24H36N2O2/c1-6-26(7-2)22(28)19-9-8-17-16-14-25-21-15(3)20(27)11-13-24(21,5)18(16)10-12-23(17,19)4/h11,13,16-19,25H,6-10,12,14H2,1-5H3/t16?,17?,18?,19-,23+,24-/m1/s1

Standard InChI Key:  YKTBZEAZRCZTMY-FNGIOQARSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  1  0  0  0  0  0999 V2000
    0.1377   -2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1419   -2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2948   -0.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -3.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8512   -3.2837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792   -0.5758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -1.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2823   -1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421    0.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5646   -2.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -1.6189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851   -2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5688   -2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2851   -2.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5814   -0.4005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8637   -0.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.9068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5549   -1.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1474    0.3713    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7955    0.8261    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9985   -3.2837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0918   -1.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2823   -0.0418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5716   -4.0973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6981   -0.2503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4186    1.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2239    1.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5075   -0.0876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  8  1  0
  4  1  2  0
  5  1  1  0
  6  3  1  0
  7  2  1  0
  8 10  1  0
  6  9  1  1
 10 13  1  0
 11  2  1  0
 12  4  1  0
 13  5  1  0
 14 12  1  0
 15 16  1  0
 16  7  1  0
 17  8  1  0
 18 17  1  0
 19  9  1  0
 20  9  2  0
 21 12  2  0
  2 22  1  1
  3 23  1  1
 24  4  1  0
 25 19  1  0
 26 19  1  0
 27 26  1  0
 28 25  1  0
  7 10  1  0
 11 14  2  0
 15  3  1  0
 18  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706585

   (1S,9aR,11aS)-N,N-diethyl-6,9a,11a-trimethyl-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: 384.56

Molecular Weight (Monoisotopic): 384.2777

AlogP: 3.94

#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: 3.07

CX LogD: 3.07

Aromatic Rings: ┄

Heavy Atoms: 28

QED Weighted: 0.80

Np Likeness Score: 1.25

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