5-(5-(2,6-Difluoro-3-hydroxy-benzoyl)-thiophen-2-yl)-2-hydroxy-benzonitrile

ID: ALA4088861

PubChem CID: 122652913

Max Phase: Preclinical

Molecular Formula: C18H9F2NO3S

Molecular Weight: 357.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)ccc1O

Standard InChI:  InChI=1S/C18H9F2NO3S/c19-11-2-4-13(23)17(20)16(11)18(24)15-6-5-14(25-15)9-1-3-12(22)10(7-9)8-21/h1-7,22-23H

Standard InChI Key:  UXTQURJUGIBMQY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   14.2499  -10.4088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2488  -11.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9568  -11.6373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6665  -11.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6636  -10.4052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9550  -10.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9526   -9.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6591   -8.7721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2436   -8.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4111   -9.1022    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.9561   -8.4932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5454   -7.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7466   -7.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7649   -8.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0987   -9.3208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9109   -9.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3902   -8.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0514   -7.9927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2402   -7.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3698   -9.9940    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5421  -10.0004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.5407  -11.6364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2443  -10.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5785  -10.8910    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2032   -8.8230    0.0000 O   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
 23 24  3  0
 16 23  1  0
 17 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4088861

   ---

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: 357.34

Molecular Weight (Monoisotopic): 357.0271

AlogP: 4.21

#Rotatable Bonds: 3

Polar Surface Area: 81.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.25

CX Basic pKa: ┄

CX LogP: 4.52

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.69

Np Likeness Score: -0.81

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