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

ID: ALA4073469

PubChem CID: 122652905

Max Phase: Preclinical

Molecular Formula: C21H15F2NO3S

Molecular Weight: 399.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)Oc1ccc(-c2ccc(C(=O)c3c(F)ccc(O)c3F)s2)cc1C#N

Standard InChI:  InChI=1S/C21H15F2NO3S/c1-11(2)27-16-6-3-12(9-13(16)10-24)17-7-8-18(28-17)21(26)19-14(22)4-5-15(25)20(19)23/h3-9,11,25H,1-2H3

Standard InChI Key:  QNYOMZLPFQSWLB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   14.5253   -5.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2333   -5.5744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9430   -5.1650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9402   -4.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2315   -3.9371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2291   -3.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9356   -2.7092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5202   -2.7134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6876   -3.0393    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.2326   -2.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8219   -1.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0231   -1.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0414   -2.5108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3753   -3.2579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1874   -3.3412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6667   -2.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3279   -1.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5168   -1.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6463   -3.9311    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8186   -3.9375    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.8173   -5.5735    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5208   -4.0824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8551   -4.8281    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4797   -2.7601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8154   -3.5052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6284   -3.5871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3379   -4.1684    0.0000 C   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
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 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
 25 26  1  0
 26 27  1  0
 26 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4073469

   ---

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: 399.42

Molecular Weight (Monoisotopic): 399.0741

AlogP: 5.29

#Rotatable Bonds: 5

Polar Surface Area: 70.32

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.47

CX Basic pKa: ┄

CX LogP: 5.44

CX LogD: 5.18

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.59

Np Likeness Score: -1.04

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