(5-(3-Chloro-4-methoxy-5-methyl-phenyl)-thiophen-2-yl)-(2,6-difluoro-3-hydroxy-phenyl)-methanone

ID: ALA4103524

PubChem CID: 122652936

Max Phase: Preclinical

Molecular Formula: C19H13ClF2O3S

Molecular Weight: 394.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1c(C)cc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc1Cl

Standard InChI:  InChI=1S/C19H13ClF2O3S/c1-9-7-10(8-11(20)19(9)25-2)14-5-6-15(26-14)18(24)16-12(21)3-4-13(23)17(16)22/h3-8,23H,1-2H3

Standard InChI Key:  YVYVHDARDZKFHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   17.1651   -4.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9823   -4.3047    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.2367   -3.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5737   -3.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9150   -3.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0105   -3.2752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6169   -3.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3938   -3.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5655   -2.7738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9540   -2.2253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1795   -2.4791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6839   -4.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8713   -4.8788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0153   -5.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5324   -6.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8631   -7.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6766   -7.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1581   -6.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8247   -5.7968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3816   -7.7793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7198   -6.2852    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3040   -5.1349    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.3427   -2.5214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9499   -3.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1222   -1.4256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0001   -4.1216    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  1  2  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3  6  1  0
  1 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 15 21  1  0
 19 22  1  0
  9 23  1  0
 23 24  1  0
 10 25  1  0
  8 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4103524

   ---

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: 394.83

Molecular Weight (Monoisotopic): 394.0242

AlogP: 5.60

#Rotatable Bonds: 4

Polar Surface Area: 46.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.72

CX Basic pKa: ┄

CX LogP: 5.93

CX LogD: 5.76

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.59

Np Likeness Score: -0.76

References

1. Abdelsamie AS, van Koppen CJ, Bey E, Salah M, Börger C, Siebenbürger L, Laschke MW, Menger MD, Frotscher M..  (2017)  Treatment of estrogen-dependent diseases: Design, synthesis and profiling of a selective 17β-HSD1 inhibitor with sub-nanomolar IC50 for a proof-of-principle study.,  127  [PMID:27852458] [10.1016/j.ejmech.2016.11.004]

Source

Source(1):

• Scientific Literature