(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-3-[[4-[3-methoxy-4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-17-one

ID: ALA4647843

PubChem CID: 156021598

Max Phase: Preclinical

Molecular Formula: C33H47F3N2O3

Molecular Weight: 576.74

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(CN2CCN(C[C@@]3(O)CC[C@@]4(C)[C@@H](CC[C@@H]5[C@@H]4CC[C@]4(C)C(=O)CC[C@@H]54)C3)CC2)ccc1C(F)(F)F

Standard InChI:  InChI=1S/C33H47F3N2O3/c1-30-12-13-32(40,19-23(30)5-6-24-25-8-9-29(39)31(25,2)11-10-26(24)30)21-38-16-14-37(15-17-38)20-22-4-7-27(33(34,35)36)28(18-22)41-3/h4,7,18,23-26,40H,5-6,8-17,19-21H2,1-3H3/t23-,24-,25-,26-,30-,31-,32+/m0/s1

Standard InChI Key:  NRMYADILAZBYBE-PQPXNBBZSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4647843

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 576.74

Molecular Weight (Monoisotopic): 576.3539

AlogP: 6.17

#Rotatable Bonds: 5

Polar Surface Area: 53.01

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.26

CX LogP: 6.00

CX LogD: 5.09

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.45

Np Likeness Score: 0.72

References

1. Boutin S, Roy J, Maltais R, Poirier D..  (2020)  Formation of 5α-dihydrotestosterone from 5α-androstane-3α,17β-diol in prostate cancer LAPC-4 cells - Identifying inhibitors of non-classical pathways producing the most potent androgen.,  30  (2): [PMID:31753699] [10.1016/j.bmcl.2019.126783]

2. Boutin S,Maltais R,Roy J,Poirier D.  (2021)  Synthesis of 17β-hydroxysteroid dehydrogenase type 10 steroidal inhibitors: Selectivity, metabolic stability and enhanced potency.,  209  [PMID:33081987] [10.1016/j.ejmech.2020.112909]

Source

Source(1):

• Scientific Literature