(4-(N-(5-Cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)-2-fluorophenyl)boronic acid

ID: ALA4548919

PubChem CID: 71263635

Max Phase: Preclinical

Molecular Formula: C26H23BF2N2O6S

Molecular Weight: 540.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNC(=O)c1c(-c2ccc(F)cc2)oc2cc(N(c3ccc(B(O)O)c(F)c3)S(C)(=O)=O)c(C3CC3)cc12

Standard InChI:  InChI=1S/C26H23BF2N2O6S/c1-30-26(32)24-19-12-18(14-3-4-14)22(13-23(19)37-25(24)15-5-7-16(28)8-6-15)31(38(2,35)36)17-9-10-20(27(33)34)21(29)11-17/h5-14,33-34H,3-4H2,1-2H3,(H,30,32)

Standard InChI Key:  ISLVVWCDXMALMX-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 38 42  0  0  0  0  0  0  0  0999 V2000
   14.8168   -4.3253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2295   -5.0352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.6379   -4.3228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6478   -4.2180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6467   -5.0375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3547   -5.4465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3529   -3.8091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0616   -4.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0618   -5.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8448   -5.2917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3285   -4.6256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8444   -3.9598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1424   -4.6239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5507   -5.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3671   -5.3331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7763   -4.6248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3631   -3.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5480   -3.9183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0966   -3.1826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8959   -3.0124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1482   -2.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5496   -2.5755    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5935   -4.6234    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9380   -3.8063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5292   -3.0987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1208   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9386   -5.4456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5232   -5.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9379   -6.2628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2277   -6.6657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2267   -7.4821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9346   -7.8921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6450   -7.4798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6425   -6.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3538   -7.8865    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.9349   -8.7093    0.0000 B   0  0  0  0  0  0  0  0  0  0  0  0
   15.2274   -9.1182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6428   -9.1176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
 11 13  1  0
 12 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  2  0
 16 23  1  0
 25 24  1  0
 26 25  1  0
 24 26  1  0
  4 24  1  0
  5 27  1  0
 27  2  1  0
  2 28  1  0
 27 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
 33 35  1  0
 32 36  1  0
 36 37  1  0
 36 38  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4548919

   4-(N-(5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-6-yl)methylsulfonamido)-2-fluorophenylboronic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 540.35

Molecular Weight (Monoisotopic): 540.1338

AlogP: ┄

#Rotatable Bonds: ┄

Polar Surface Area: ┄

Molecular Species: ┄

HBA: ┄

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): ┄

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: ┄

CX LogD: ┄

Aromatic Rings: ┄

Heavy Atoms: ┄

QED Weighted: ┄

Np Likeness Score: ┄

References

1. Chong PY, Shotwell JB, Miller J, Price DJ, Maynard A, Voitenleitner C, Mathis A, Williams S, Pouliot JJ, Creech K, Wang F, Fang J, Zhang H, Tai VW, Turner E, Kahler KM, Crosby R, Peat AJ..  (2019)  Design of N-Benzoxaborole Benzofuran GSK8175-Optimization of Human Pharmacokinetics Inspired by Metabolites of a Failed Clinical HCV Inhibitor.,  62  (7): [PMID:30763090] [10.1021/acs.jmedchem.8b01719]

Source

Source(1):

• Scientific Literature