(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 benzhydryl-amide

ID: ALA24088

Max Phase: Preclinical

Molecular Formula: C32H38N2O2

Molecular Weight: 482.67

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

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

Standard InChI: InChI=1S/C32H38N2O2/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/h3-12,19,24-27,29,33H,13-18,20H2,1-2H3,(H,34,36)/t24?,25?,26?,27-,31+,32-/m1/s1

Standard InChI Key: WOJPQMHAJQJQJK-XXRHFDIKSA-N

Molfile:

     RDKit          2D

 36 41  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
    4.4667   -4.9792    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
    5.2625   -4.7542    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
    2.0292   -8.4792    0.0000 N   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
    5.4750   -3.9625    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
    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
    6.2667   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8875   -3.3792    0.0000 C   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
    1.3167   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8500   -4.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4667   -2.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1000   -2.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0917   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5125   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5042   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6417   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -2.2250    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
  9  5  1  1
  6 15  1  0
  7  4  1  0
  8  5  1  0
  9  1  1  0
 10 14  1  0
 11  3  2  0
 12  8  1  0
 13  1  1  0
 14  7  1  0
 15 13  1  0
 16  4  1  0
 17  2  1  0
 18  9  1  0
 19 24  1  0
 20  5  2  0
 21 12  1  0
 22 12  1  0
 23 19  2  0
 24 17  1  0
  1 25  1  1
  2 26  1  1
 27 21  2  0
 28 21  1  0
 29 22  2  0
 30 22  1  0
 31 28  2  0
 32 29  1  0
 33 30  2  0
 34 27  1  0
 35 31  1  0
 36 33  1  0
 16 18  1  0
  7  6  1  0
  3 10  1  0
 11 19  1  0
 32 36  2  0
 34 35  2  0
M  END

Associated Targets(Human)

SRD5A1 Tclin Steroid 5-alpha-reductase 1 (755 Activities)

Discover Target: SRD5A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SRD5A2 Tclin Steroid 5-alpha-reductase 2 (937 Activities)

Discover Target: SRD5A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HSD3B1 Tchem 3-beta-hydroxysteroid dehydrogenase/delta 5-->4-isomerase type I (15 Activities)

Discover Target: HSD3B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

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

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: 482.67	Molecular Weight (Monoisotopic): 482.2933	AlogP: 5.81	#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: 13.42	CX Basic pKa: ┄	CX LogP: 5.25	CX LogD: 5.25
Aromatic Rings: 2	Heavy Atoms: 36	QED Weighted: 0.58	Np Likeness Score: 0.76

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]

(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 benzhydryl-amide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Associated Targets(non-human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source