(8R,9S,13S,14S)-2-Bromo-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one(8R,9S,13S,14S)-2-Bromo-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one

ID: ALA189051

Chembl Id: CHEMBL189051

PubChem CID: 11530377

Max Phase: Preclinical

Molecular Formula: C18H21BrO2

Molecular Weight: 349.27

Molecule Type: Small molecule

Names and Identifiers

Synonyms: 2-Bromoestrone | CHEMBL189051|2-Bromoestrone|SCHEMBL4590030|BDBM50311659|(8R,9S,13S,14S)-2-Bromo-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one(8R,9S,13S,14S)-2-Bromo-3-hydroxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-17-one|(8R,9S,13S,14S)-2-bromo-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

Canonical SMILES:  C[C@]12CC[C@@H]3c4cc(Br)c(O)cc4CC[C@H]3[C@@H]1CCC2=O

Standard InChI:  InChI=1S/C18H21BrO2/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-16(20)15(19)9-13(10)11/h8-9,11-12,14,20H,2-7H2,1H3/t11-,12+,14-,18-/m0/s1

Standard InChI Key:  JVITVXNLPKMREE-JPVZDGGYSA-N

Alternative Forms

1. Parent:

   

   ALA189051

   (8R,9S,13S,14S)-2-bromo-3-hydroxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-6H-cyclopenta[a]phenanthren-17(14H)-one

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: 349.27

Molecular Weight (Monoisotopic): 348.0725

AlogP: 4.58

#Rotatable Bonds: ┄

Polar Surface Area: 37.30

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 2

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.48

CX Basic pKa: ┄

CX LogP: 5.08

CX LogD: 5.04

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.74

Np Likeness Score: 1.94

References

1. Leese MP, Hejaz HA, Mahon MF, Newman SP, Purohit A, Reed MJ, Potter BV..  (2005)  A-ring-substituted estrogen-3-O-sulfamates: potent multitargeted anticancer agents.,  48  (16): [PMID:16078843] [10.1021/jm050066a]

2. Möller G, Deluca D, Gege C, Rosinus A, Kowalik D, Peters O, Droescher P, Elger W, Adamski J, Hillisch A..  (2009)  Structure-based design, synthesis and in vitro characterization of potent 17beta-hydroxysteroid dehydrogenase type 1 inhibitors based on 2-substitutions of estrone and D-homo-estrone.,  19  (23): [PMID:19836949] [10.1016/j.bmcl.2009.09.113]

3. Phan CM, Liu Y, Kim BM, Mostafa Y, Taylor SD..  (2011)  Inhibition of steroid sulfatase with 4-substituted estrone and estradiol derivatives.,  19  (20): [PMID:21925885] [10.1016/j.bmc.2011.08.046]

4. Yadav MR, Barmade MA, Tamboli RS, Murumkar PR..  (2015)  Developing steroidal aromatase inhibitors-an effective armament to win the battle against breast cancer.,  105  [PMID:26469743] [10.1016/j.ejmech.2015.09.038]

5. Adhikari N, Baidya SK, Jha T..  (2020)  Effective anti-aromatase therapy to battle against estrogen-mediated breast cancer: Comparative SAR/QSAR assessment on steroidal aromatase inhibitors.,  208  [PMID:33017749] [10.1016/j.ejmech.2020.112845]

Source

Source(1):

• Scientific Literature