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

ID: ALA1079595

Chembl Id: CHEMBL1079595

PubChem CID: 11493223

Max Phase: Preclinical

Molecular Formula: C18H21ClO2

Molecular Weight: 304.82

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C18H21ClO2/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:  CESQEGKZVXLYKV-JPVZDGGYSA-N

Alternative Forms

1. Parent:

   

   ALA1079595

   2-Chloroestrone

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: 304.82

Molecular Weight (Monoisotopic): 304.1230

AlogP: 4.47

#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: 8.28

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 4.86

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.77

Np Likeness Score: 1.77

References

1. 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]

2. 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]

3. 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