(1S,9aR,11aS)-9a,11a-Dimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid methyl ester

ID: ALA297524

Max Phase: Preclinical

Molecular Formula: C20H29NO3

Molecular Weight: 331.46

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H29NO3/c1-19-9-7-15-13(14(19)4-5-16(19)18(23)24-3)11-21-17-10-12(22)6-8-20(15,17)2/h10,13-16,21H,4-9,11H2,1-3H3/t13?,14?,15?,16-,19+,20-/m1/s1

Standard InChI Key:  ZJOMBWSBLZDZAK-YANZXGQTSA-N

Molfile:  

     RDKit          2D

 24 27  0  0  1  0  0  0  0  0999 V2000
    3.4750   -6.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -6.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7417   -7.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0292   -8.4792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542   -5.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -8.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4667   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -8.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0417   -6.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -7.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -6.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7292   -6.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8792   -4.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -8.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0958   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4667   -5.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2625   -4.7542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3167   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -5.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0
  3  2  1  0
  4  1  1  0
  5 13  1  0
  6  4  1  0
  7 12  1  0
  8  1  1  0
  9  3  2  0
 10  1  1  0
  8 11  1  1
 12  6  1  0
 13 10  1  0
 14  4  1  0
 15  2  1  0
 16  8  1  0
 17 20  1  0
 18 11  2  0
 19 17  2  0
 20 15  1  0
  1 21  1  1
 22 11  1  0
  2 23  1  1
 24 22  1  0
 14 16  1  0
  6  5  1  0
  3  7  1  0
  9 17  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA297524

   ---

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: 331.46

Molecular Weight (Monoisotopic): 331.2147

AlogP: 3.07

#Rotatable Bonds: 1

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: ┄

Heavy Atoms: 24

QED Weighted: 0.75

Np Likeness Score: 1.77

References

1. Kenny B, Ballard S, Blagg J, Fox D..  (1997)  Pharmacological options in the treatment of benign prostatic hyperplasia.,  40  (9): [PMID:9135028] [10.1021/jm960697s]

2. 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]

3. Frye SV, Haffner CD, Maloney PR, Mook RA, Dorsey GF, Hiner RN, Batchelor KW, Bramson HN, Stuart JD, Schweiker SL..  (1993)  6-Azasteroids: potent dual inhibitors of human type 1 and 2 steroid 5 alpha-reductase.,  36  (26): [PMID:8277514] [10.1021/jm00078a022]

4. Guarna, A A and 8 more authors.  2000-10-05  Benzo[c]quinolizin-3-ones: a novel class of potent and selective nonsteroidal inhibitors of human steroid 5alpha-reductase 1.  [PMID:11020287]

5. Hartmann, R W RW and 5 more authors.  2000-11-02  Synthesis and evaluation of novel steroidal oxime inhibitors of P450 17 (17 alpha-hydroxylase/C17-20-lyase) and 5 alpha-reductase types 1 and 2.  [PMID:11063622]

6. Occhiato, Ernesto G EG and 11 more authors.  2004-07-01  Synthesis, biological activity, and three-dimensional quantitative structure-activity relationship model for a series of benzo[c]quinolizin-3-ones, nonsteroidal inhibitors of human steroid 5alpha-reductase 1.  [PMID:15214782]

7. Handratta, Venkatesh D VD and 10 more authors.  2005-04-21  Novel C-17-heteroaryl steroidal CYP17 inhibitors/antiandrogens: synthesis, in vitro biological activity, pharmacokinetics, and antitumor activity in the LAPC4 human prostate cancer xenograft model.  [PMID:15828836]

8. Lao, Kejing K and 6 more authors.  2017-09-01  Design, synthesis and biological evaluation of novel 3-oxo-4-oxa-5α-androst-17β-amide derivatives as dual 5α-reductase inhibitors and androgen receptor antagonists.  [PMID:28757062]

Source

Source(1):

• Scientific Literature