3-{[(16beta,17beta)-3-(2-bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

ID: ALA2203397

Chembl Id: CHEMBL2203397

PubChem CID: 53494954

Max Phase: Preclinical

Molecular Formula: C28H34BrNO2

Molecular Weight: 496.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@]12CC[C@@H]3c4ccc(CCBr)cc4CC[C@H]3[C@@H]1C[C@H](Cc1cccc(C(N)=O)c1)[C@@H]2O

Standard InChI:  InChI=1S/C28H34BrNO2/c1-28-11-9-23-22-7-5-17(10-12-29)13-19(22)6-8-24(23)25(28)16-21(26(28)31)15-18-3-2-4-20(14-18)27(30)32/h2-5,7,13-14,21,23-26,31H,6,8-12,15-16H2,1H3,(H2,30,32)/t21-,23+,24+,25-,26-,28-/m0/s1

Standard InChI Key:  LSFSILMVQQMGRP-OPRSCSRJSA-N

Alternative Forms

1. Parent:

   

   ALA2203397

   3-{[(16beta,17beta)-3-(2-Bromoethyl)-17-hydroxyestra-1(10),2,4-trien-16-yl]methyl}benzamide

Molecule Features

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: 496.49

Molecular Weight (Monoisotopic): 495.1773

AlogP: 5.41

#Rotatable Bonds: 5

Polar Surface Area: 63.32

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.90

CX LogD: 5.90

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: 1.14

References

1. Maltais R, Ayan D, Poirier D..  (2011)  Crucial Role of 3-Bromoethyl in Removing the Estrogenic Activity of 17β-HSD1 Inhibitor 16β-(m-Carbamoylbenzyl)estradiol.,  2  (9): [PMID:21927646] [10.1021/ml200093v]

2. Maltais R, Ayan D, Trottier A, Barbeau X, Lagüe P, Bouchard JE, Poirier D..  (2014)  Discovery of a non-estrogenic irreversible inhibitor of 17β-hydroxysteroid dehydrogenase type 1 from 3-substituted-16β-(m-carbamoylbenzyl)-estradiol derivatives.,  57  (1): [PMID:24328103] [10.1021/jm401639v]

Source

Source(1):

• Scientific Literature