(1S,9aR,11aS)-6,9a,11a-Trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid (4-chloro-phenyl)-cyclopentyl-amide

ID: ALA283123

Max Phase: Preclinical

Molecular Formula: C31H41ClN2O2

Molecular Weight: 509.13

Molecule Type: Small molecule

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC1=C2NCC3C(CC[C@@]4(C)C3CC[C@@H]4C(=O)N(c3ccc(Cl)cc3)C3CCCC3)[C@@]2(C)CCC1=O

Standard InChI: InChI=1S/C31H41ClN2O2/c1-19-27(35)15-17-31(3)25-14-16-30(2)24(23(25)18-33-28(19)31)12-13-26(30)29(36)34(21-6-4-5-7-21)22-10-8-20(32)9-11-22/h8-11,21,23-26,33H,4-7,12-18H2,1-3H3/t23?,24?,25?,26-,30+,31-/m1/s1

Standard InChI Key: HCXSUZWCTCKJCT-GIDNVIJNSA-N

Molfile:

     RDKit          2D

 36 41  0  0  1  0  0  0  0  0999 V2000
    1.8792   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8875   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292   -3.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0375   -4.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -6.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8167   -4.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -6.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6000   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -5.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -3.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3125   -6.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292   -4.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1750   -5.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2917   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4417   -2.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4125   -3.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -2.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -1.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8792   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0292   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4542   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1792   -7.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6542   -1.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0417   -1.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6625   -0.0667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -4.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2292   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0292   -5.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  6  3  1  1
  4  9  1  0
  5  1  2  0
  6  4  1  0
  7  1  1  0
  8  2  1  0
  9 10  1  0
 10 12  1  0
 11  3  1  0
 12  7  1  0
 13  5  1  0
 14 16  1  0
 15  2  1  0
 16  8  1  0
 17 18  1  0
 18  9  1  0
 19  3  2  0
 20 11  1  0
 21 13  1  0
 22 13  2  0
 23 11  1  0
 24 20  2  0
 25 20  1  0
  2 26  1  1
  4 27  1  1
 28 30  1  0
 29  5  1  0
 30 25  2  0
 31 24  1  0
 32 28  1  0
 33 23  1  0
 34 23  1  0
 35 34  1  0
 36 33  1  0
 10  8  1  0
 21 15  1  0
 14  4  1  0
  6 17  1  0
 35 36  1  0
 28 31  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: 509.13	Molecular Weight (Monoisotopic): 508.2857	AlogP: 6.92	#Rotatable Bonds: 3
Polar Surface Area: 49.41	Molecular Species: NEUTRAL	HBA: 3	HBD: 1
#RO5 Violations: 2	HBA (Lipinski): 4	HBD (Lipinski): 1	#RO5 Violations (Lipinski): 2
CX Acidic pKa: ┄	CX Basic pKa: ┄	CX LogP: 5.98	CX LogD: 5.98
Aromatic Rings: 1	Heavy Atoms: 36	QED Weighted: 0.48	Np Likeness Score: 0.51

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)-6,9a,11a-Trimethyl-7-oxo-2,3,3a,3b,4,5,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[i]phenanthridine-1-carboxylic acid (4-chloro-phenyl)-cyclopentyl-amide

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source