(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 benzhydryl-amide

ID: ALA3706581

PubChem CID: 44315430

Max Phase: Preclinical

Molecular Formula: C32H36N2O2

Molecular Weight: 480.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12C=CC(=O)C=C1NCC1C2CC[C@@]2(C)C1CC[C@@H]2C(=O)NC(c1ccccc1)c1ccccc1

Standard InChI:  InChI=1S/C32H36N2O2/c1-31-18-16-26-24(20-33-28-19-23(35)15-17-32(26,28)2)25(31)13-14-27(31)30(36)34-29(21-9-5-3-6-10-21)22-11-7-4-8-12-22/h3-12,15,17,19,24-27,29,33H,13-14,16,18,20H2,1-2H3,(H,34,36)/t24?,25?,26?,27-,31+,32-/m1/s1

Standard InChI Key:  FCSFHDMKKMNQRX-XXRHFDIKSA-N

Molfile:  

     RDKit          2D

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    6.5407    0.5848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6031    1.5805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2 14  1  0
  3  1  1  0
  4  7  1  0
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 20 19  1  0
 21  5  2  0
 22 13  1  0
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  2 25  1  1
  1 26  1  1
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 28 23  1  0
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 31 28  2  0
 32 29  1  0
 33 30  2  0
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 12 20  1  0
 10 15  1  0
  4  2  1  0
 18  9  1  0
 34 35  2  0
 32 36  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3706581

   (1S,9aR,11aS)-N-benzhydryl-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: 480.65

Molecular Weight (Monoisotopic): 480.2777

AlogP: 5.58

#Rotatable Bonds: 4

Polar Surface Area: 58.20

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.40

CX Basic pKa: ┄

CX LogP: 5.25

CX LogD: 5.25

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.60

Np Likeness Score: 0.83

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