(1S,9aR,11aS)-6-Chloro-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 (4-chloro-phenyl)-cyclopentyl-amide

ID: ALA283430

Max Phase: Preclinical

Molecular Formula: C30H38Cl2N2O2

Molecular Weight: 529.55

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(Cl)=C1NCC1C2CC[C@@]2(C)C1CC[C@@H]2C(=O)N(c1ccc(Cl)cc1)C1CCCC1

Standard InChI: InChI=1S/C30H38Cl2N2O2/c1-29-15-13-23-21(17-33-27-26(32)25(35)14-16-30(23,27)2)22(29)11-12-24(29)28(36)34(19-5-3-4-6-19)20-9-7-18(31)8-10-20/h7-10,19,21-24,33H,3-6,11-17H2,1-2H3/t21?,22?,23?,24-,29+,30-/m1/s1

Standard InChI Key: BBYABNFXUAVLAL-OFZUXSOTSA-N

Molfile:

     RDKit          2D

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   -0.2500   -6.9792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    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
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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: 529.55	Molecular Weight (Monoisotopic): 528.2310	AlogP: 7.10	#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: 5.97	CX LogD: 5.97
Aromatic Rings: 1	Heavy Atoms: 36	QED Weighted: 0.45	Np Likeness Score: 0.45

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-Chloro-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 (4-chloro-phenyl)-cyclopentyl-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