5-(4-chlorophenyl)-3-(ethoxy(vinyl)phosphorylamino)thiophene-2-carboxylic acid

ID: ALA4557948

PubChem CID: 155554806

Max Phase: Preclinical

Molecular Formula: C15H15ClNO4PS

Molecular Weight: 371.78

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C=CP(=O)(Nc1cc(-c2ccc(Cl)cc2)sc1C(=O)O)OCC

Standard InChI:  InChI=1S/C15H15ClNO4PS/c1-3-21-22(20,4-2)17-12-9-13(23-14(12)15(18)19)10-5-7-11(16)8-6-10/h4-9H,2-3H2,1H3,(H,17,20)(H,18,19)

Standard InChI Key:  NXUJCNOIYBLKQP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   16.1737  -16.8307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8210  -17.3295    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   17.4966  -16.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2658  -16.0830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4498  -16.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2656  -17.1445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4105  -17.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1791  -18.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8033  -17.6967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6539  -16.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8854  -16.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3873  -17.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7965  -16.4967    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1938  -17.8552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9880  -15.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.3407  -14.6516    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.1575  -14.6754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8794  -13.9773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5225  -14.6434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1069  -15.3470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5730  -17.9712    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.2898  -15.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5459  -15.3916    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
 12 13  1  0
 12 14  2  0
  1 12  1  0
  5 15  1  0
 15 16  1  0
 17 16  1  0
 16 18  2  0
 16 19  1  0
 19 20  1  0
  9 21  1  0
 20 22  1  0
 17 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4557948

   ---

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: 371.78

Molecular Weight (Monoisotopic): 371.0148

AlogP: 5.55

#Rotatable Bonds: 7

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.26

CX Basic pKa: ┄

CX LogP: 3.40

CX LogD: -0.08

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -0.78

References

1. Pierra Rouvière C, Amador A, Badaroux E, Convard T, Da Costa D, Dukhan D, Griffe L, Griffon JF, LaColla M, Leroy F, Liuzzi M, Loi AG, McCarville J, Mascia V, Milhau J, Onidi L, Paparin JL, Rahali R, Sais E, Seifer M, Surleraux D, Standring D, Dousson C..  (2016)  Synthesis of potent and broad genotypically active NS5B HCV non-nucleoside inhibitors binding to the thumb domain allosteric site 2 of the viral polymerase.,  26  (18): [PMID:27520942] [10.1016/j.bmcl.2016.01.042]

Source

Source(1):

• Scientific Literature