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

ID: ALA4063985

PubChem CID: 91820627

Max Phase: Preclinical

Molecular Formula: C18H11ClF2O3S

Molecular Weight: 380.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc(Cl)c1O

Standard InChI:  InChI=1S/C18H11ClF2O3S/c1-8-6-9(7-10(19)17(8)23)13-4-5-14(25-13)18(24)15-11(20)2-3-12(22)16(15)21/h2-7,22-23H,1H3

Standard InChI Key:  NBPPEXVETXEPTG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   17.2559  -14.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0731  -14.1399    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.3275  -13.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6645  -12.8811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0058  -13.3632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1013  -13.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7077  -13.6598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4846  -13.4089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6563  -12.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0448  -12.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2703  -12.3143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7747  -14.8004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9621  -14.7139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1061  -15.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6232  -16.2078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9539  -16.9542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7674  -17.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2489  -16.3757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9155  -15.6319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4724  -17.6144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8106  -16.1204    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.3948  -14.9701    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.4335  -12.3565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.0909  -13.9568    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   20.2130  -11.2608    0.0000 C   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
  8 24  1  0
 10 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4063985

   [5-(3-Chloro-4-hydroxy-5-methylphenyl)thiophen-2-yl]-(2,6-difluoro-3-hydroxyphenyl)methanone

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: 380.80

Molecular Weight (Monoisotopic): 380.0085

AlogP: 5.30

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.50

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 5.50

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -0.69

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