(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 (3,5-di-tert-butyl-phenyl)-amide

ID: ALA25516

Max Phase: Preclinical

Molecular Formula: C33H48N2O2

Molecular Weight: 504.76

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(C)(C)c1cc(NC(=O)[C@H]2CCC3C4CNC5=CC(=O)CC[C@]5(C)C4CC[C@@]32C)cc(C(C)(C)C)c1

Standard InChI: InChI=1S/C33H48N2O2/c1-30(2,3)20-15-21(31(4,5)6)17-22(16-20)35-29(37)27-10-9-25-24-19-34-28-18-23(36)11-13-33(28,8)26(24)12-14-32(25,27)7/h15-18,24-27,34H,9-14,19H2,1-8H3,(H,35,37)/t24?,25?,26?,27-,32+,33-/m1/s1

Standard InChI Key: VEAHYIFQNRGWBM-AUQMWIRBSA-N

Molfile:

     RDKit          2D

 37 41  0  0  1  0  0  0  0  0999 V2000
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    3.9417   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9417   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8792   -3.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6542   -6.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2292   -6.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8792   -2.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -0.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1250   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -3.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -5.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0917   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6625   -3.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5500    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.3542   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1750    0.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8917   -1.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -2.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8042   -6.1042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5250   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0875   -2.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9375   -4.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000    1.1833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667    0.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917    0.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4917   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1542    0.3958    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 17  1  0
  6  4  1  0
  8  7  1  1
  8  1  1  0
  9 15  1  0
 10  3  2  0
 11  7  1  0
 12 26  2  0
 13 25  1  0
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 20  2  1  0
 21  8  1  0
 22 29  1  0
 23 12  1  0
 24 13  1  0
 25 16  2  0
 26 16  1  0
 27  7  2  0
 28 22  2  0
 29 20  1  0
  1 30  1  1
  2 31  1  1
 32 24  1  0
 33 23  1  0
 34 23  1  0
 35 23  1  0
 36 24  1  0
 37 24  1  0
 18 21  1  0
  6  5  1  0
  3  9  1  0
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 13 19  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: 504.76	Molecular Weight (Monoisotopic): 504.3716	AlogP: 7.14	#Rotatable Bonds: 2
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: 13.98	CX Basic pKa: ┄	CX LogP: 6.85	CX LogD: 6.85
Aromatic Rings: 1	Heavy Atoms: 37	QED Weighted: 0.45	Np Likeness Score: 0.57

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, Hiner RN, Dorsey GF, Noe RA, Unwalla RJ, Batchelor KW, Bramson HN, Stuart JD.. (1995) 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 by 6-azaandrost-4-en-3-ones: optimization of the C17 substituent., 38 (14): [PMID:7629802] [10.1021/jm00014a015]
3. 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]
4. 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]
5. 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]
6. 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]
7. 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 (3,5-di-tert-butyl-phenyl)-amide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source