3-(3,17beta-dihydroxy-estra-1,3,5(10)-trien-16beta-ylmethyl)-benzamide

ID: ALA410242

Chembl Id: CHEMBL410242

PubChem CID: 44456599

Max Phase: Preclinical

Molecular Formula: C26H31NO3

Molecular Weight: 405.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 16Beta-(M-Carbamoylbenzyl)Estradiol | CHEMBL410242|3-{[(9beta,14beta,16alpha,17alpha)-3,17-dihydroxyestra-1,3,5(10)-trien-16-yl]methyl}benzamide|E2B|3hb4|16Beta-(M-Carbamoylbenzyl)Estradiol|BDBM50373700|Q27459830

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

Standard InChI:  InChI=1S/C26H31NO3/c1-26-10-9-21-20-8-6-19(28)13-16(20)5-7-22(21)23(26)14-18(24(26)29)12-15-3-2-4-17(11-15)25(27)30/h2-4,6,8,11,13,18,21-24,28-29H,5,7,9-10,12,14H2,1H3,(H2,27,30)/t18-,21+,22+,23-,24-,26-/m0/s1

Standard InChI Key:  RSVOVHDOLNWYER-RYZVYYIHSA-N

Alternative Forms

1. Parent:

   

   ALA410242

   3-{[(9beta,14beta,16alpha,17alpha)-3,17-Dihydroxyestra-1,3,5(10)-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: 405.54

Molecular Weight (Monoisotopic): 405.2304

AlogP: 4.18

#Rotatable Bonds: 3

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 3

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.33

CX Basic pKa: ┄

CX LogP: 4.54

CX LogD: 4.54

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.72

Np Likeness Score: 1.46

References

1. Laplante Y, Cadot C, Fournier MA, Poirier D..  (2008)  Estradiol and estrone C-16 derivatives as inhibitors of type 1 17beta-hydroxysteroid dehydrogenase: blocking of ER+ breast cancer cell proliferation induced by estrone.,  16  (4): [PMID:18035543] [10.1016/j.bmc.2007.11.007]

2. Ouellet E, Ayan D, Poirier D..  (2011)  Synthesis and preliminary evaluation of a modified estradiol-core bearing a fused γ-lactone as non-estrogenic inhibitor of 17β-hydroxysteroid dehydrogenase type 1.,  21  (18): [PMID:21782424] [10.1016/j.bmcl.2011.06.110]

3. 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]

4. 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