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

ID: ALA4091749

PubChem CID: 122653041

Max Phase: Preclinical

Molecular Formula: C17H8Cl2F2O3S

Molecular Weight: 401.22

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc(-c2cc(Cl)c(O)c(Cl)c2)s1)c1c(F)ccc(O)c1F

Standard InChI:  InChI=1S/C17H8Cl2F2O3S/c18-8-5-7(6-9(19)16(8)23)12-3-4-13(25-12)17(24)14-10(20)1-2-11(22)15(14)21/h1-6,22-23H

Standard InChI Key:  NQBPRKUJPGFZQA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   33.5406   -9.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5394  -10.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2475  -10.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9571  -10.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9543   -9.4436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2457   -9.0383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2432   -8.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.9497   -7.8104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5343   -7.8147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.7018   -8.1405    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   36.2468   -7.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.8360   -6.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0373   -6.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0556   -7.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3894   -8.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.2016   -8.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6808   -7.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3421   -7.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5309   -6.9514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6605   -9.0323    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.8328   -9.0388    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   32.8314  -10.6748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5358   -9.1881    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   39.4939   -7.8613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8226   -6.3605    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13  8  2  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
 11 14  1  0
  5 20  1  0
  1 21  1  0
  2 22  1  0
 16 23  1  0
 17 24  1  0
 18 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4091749

   ---

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: 401.22

Molecular Weight (Monoisotopic): 399.9539

AlogP: 5.64

#Rotatable Bonds: 3

Polar Surface Area: 57.53

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.07

CX Basic pKa: ┄

CX LogP: 5.88

CX LogD: 4.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.56

Np Likeness Score: -0.67

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