ID: ALA511530

Max Phase: Preclinical

Molecular Formula: C16H12O2S

Molecular Weight: 268.34

Molecule Type: Small molecule

Representations

Canonical SMILES:  Oc1cccc(-c2ccc(-c3cccc(O)c3)s2)c1

Standard InChI:  InChI=1S/C16H12O2S/c17-13-5-1-3-11(9-13)15-7-8-16(19-15)12-4-2-6-14(18)10-12/h1-10,17-18H

Standard InChI Key:  SVBBCXVMACPXGW-UHFFFAOYSA-N

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

Properties

Molecular Weight: 268.34

Molecular Weight (Monoisotopic): 268.0558

AlogP: 4.49

#Rotatable Bonds: 2

Polar Surface Area: 40.46

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 2

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.39

CX Basic pKa:

CX LogP: 4.43

CX LogD: 4.43

Aromatic Rings: 3

Heavy Atoms: 19

QED Weighted: 0.72

Np Likeness Score: -0.08

References

1. Bey E, Marchais-Oberwinkler S, Werth R, Negri M, Al-Soud YA, Kruchten P, Oster A, Frotscher M, Birk B, Hartmann RW..  (2008)  Design, synthesis, biological evaluation and pharmacokinetics of bis(hydroxyphenyl) substituted azoles, thiophenes, benzenes, and aza-benzenes as potent and selective nonsteroidal inhibitors of 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1).,  51  (21): [PMID:18855374] [10.1021/jm8006917]

2. Bey E, Marchais-Oberwinkler S, Negri M, Kruchten P, Oster A, Klein T, Spadaro A, Werth R, Frotscher M, Birk B, Hartmann RW..  (2009)  New insights into the SAR and binding modes of bis(hydroxyphenyl)thiophenes and -benzenes: influence of additional substituents on 17beta-hydroxysteroid dehydrogenase type 1 (17beta-HSD1) inhibitory activity and selectivity.,  52  (21): [PMID:19831396] [10.1021/jm901195w]

3. Perspicace E, Cozzoli L, Gargano EM, Hanke N, Carotti A, Hartmann RW, Marchais-Oberwinkler S..  (2014)  Novel, potent and selective 17β-hydroxysteroid dehydrogenase type 2 inhibitors as potential therapeutics for osteoporosis with dual human and mouse activities.,  83  [PMID:24974351] [10.1016/j.ejmech.2014.06.036]

4. Abdelsamie AS, Bey E, Hanke N, Empting M, Hartmann RW, Frotscher M..  (2014)  Inhibition of 17β-HSD1: SAR of bicyclic substituted hydroxyphenylmethanones and discovery of new potent inhibitors with thioether linker.,  82  [PMID:24929290] [10.1016/j.ejmech.2014.05.074]

Source

Source(1):

• Scientific Literature