(3R,5S,8R,9S,10S,13S,14S)-3-hydroxy-3-[[4-[(2-methoxy-4-methyl-phenyl)methyl]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: ALA4642468

PubChem CID: 156016677

Max Phase: Preclinical

Molecular Formula: C33H50N2O3

Molecular Weight: 522.77

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(C)ccc1CN1CCN(C[C@@]2(O)CC[C@@]3(C)[C@@H](CC[C@@H]4[C@@H]3CC[C@]3(C)C(=O)CC[C@@H]43)C2)CC1

Standard InChI:  InChI=1S/C33H50N2O3/c1-23-5-6-24(29(19-23)38-4)21-34-15-17-35(18-16-34)22-33(37)14-13-31(2)25(20-33)7-8-26-27-9-10-30(36)32(27,3)12-11-28(26)31/h5-6,19,25-28,37H,7-18,20-22H2,1-4H3/t25-,26-,27-,28-,31-,32-,33+/m0/s1

Standard InChI Key:  JDHQLVHWJRAJEX-ZJHSDCFHSA-N

Molfile:  

 
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M  END

Alternative Forms

1. Parent:

   

   ALA4642468

   ---

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: 522.77

Molecular Weight (Monoisotopic): 522.3821

AlogP: 5.46

#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: 8.23

CX LogP: 5.64

CX LogD: 4.75

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.56

Np Likeness Score: 0.87

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