3-(((2,4-dimethylphenyl)(methoxy)phosphoryl)(isopropyl)amino)-5-(4-fluorophenyl)thiophene-2-carboxylic acid

ID: ALA4533843

PubChem CID: 155547041

Max Phase: Preclinical

Molecular Formula: C23H25FNO4PS

Molecular Weight: 461.50

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COP(=O)(c1ccc(C)cc1C)N(c1cc(-c2ccc(F)cc2)sc1C(=O)O)C(C)C

Standard InChI:  InChI=1S/C23H25FNO4PS/c1-14(2)25(30(28,29-5)20-11-6-15(3)12-16(20)4)19-13-21(31-22(19)23(26)27)17-7-9-18(24)10-8-17/h6-14H,1-5H3,(H,26,27)

Standard InChI Key:  SGWMOZFWPXVBAG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   15.2988  -20.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9460  -21.1307    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.6216  -20.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3909  -19.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5748  -19.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3906  -20.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5356  -21.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3041  -22.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9283  -21.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7789  -20.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0105  -20.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5123  -20.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9215  -20.2979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3188  -21.6564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1131  -19.1897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4657  -18.4528    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.2826  -18.4766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0044  -17.7784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6475  -18.4446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6980  -21.7724    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.6665  -19.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4826  -19.2197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9124  -18.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5202  -17.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7054  -17.7814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7293  -18.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3139  -17.0641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2461  -17.7328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2983  -19.2526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8365  -18.5784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9454  -19.9896    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
  9 20  1  0
 17 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 17  1  0
 23 26  1  0
 25 27  1  0
 19 28  1  0
 15 29  1  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4533843

   ---

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: 461.50

Molecular Weight (Monoisotopic): 461.1226

AlogP: 6.25

#Rotatable Bonds: 7

Polar Surface Area: 66.84

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.25

CX Basic pKa: ┄

CX LogP: 5.81

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.42

Np Likeness Score: -0.95

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