(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 [bis-(4-chloro-phenyl)-methyl]-amide

ID: ALA412425

Max Phase: Preclinical

Molecular Formula: C32H36Cl2N2O2

Molecular Weight: 551.56

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(c1ccc(Cl)cc1)c1ccc(Cl)cc1

Standard InChI: InChI=1S/C32H36Cl2N2O2/c1-31-16-14-26-24(18-35-28-17-23(37)13-15-32(26,28)2)25(31)11-12-27(31)30(38)36-29(19-3-7-21(33)8-4-19)20-5-9-22(34)10-6-20/h3-10,17,24-27,29,35H,11-16,18H2,1-2H3,(H,36,38)/t24?,25?,26?,27-,31+,32-/m1/s1

Standard InChI Key: IQDPQNZYVDAQDB-XXRHFDIKSA-N

Molfile:

     RDKit          2D

 38 43  0  0  1  0  0  0  0  0999 V2000
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    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
    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
    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
    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
   -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
    3.7167   -2.2250    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
    1.3167   -6.4167    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
    7.6417   -4.1042    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
    7.2667   -2.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6500   -3.0875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.1292   -1.6417    0.0000 Cl  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
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 11  3  2  0
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 22  5  2  0
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 25 20  1  0
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  1 29  1  1
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  2 32  1  1
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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: 551.56	Molecular Weight (Monoisotopic): 550.2154	AlogP: 7.11	#Rotatable Bonds: 4
Polar Surface Area: 58.20	Molecular Species: NEUTRAL	HBA: 3	HBD: 2
#RO5 Violations: 2	HBA (Lipinski): 4	HBD (Lipinski): 2	#RO5 Violations (Lipinski): 2
CX Acidic pKa: 12.90	CX Basic pKa: ┄	CX LogP: 6.46	CX LogD: 6.46
Aromatic Rings: 2	Heavy Atoms: 38	QED Weighted: 0.43	Np Likeness Score: 0.58

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 [bis-(4-chloro-phenyl)-methyl]-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