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

ID: ALA4445547

PubChem CID: 59481560

Max Phase: Preclinical

Molecular Formula: C20H25ClNO4PS

Molecular Weight: 441.92

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(Nc1cc(-c2ccc(Cl)cc2)sc1C(=O)O)C1CCC(C)CC1

Standard InChI:  InChI=1S/C20H25ClNO4PS/c1-3-26-27(25,16-10-4-13(2)5-11-16)22-17-12-18(28-19(17)20(23)24)14-6-8-15(21)9-7-14/h6-9,12-13,16H,3-5,10-11H2,1-2H3,(H,22,25)(H,23,24)

Standard InChI Key:  MUQPLADEDVFRRV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   21.0480   -4.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6952   -4.6259    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.3709   -4.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1401   -3.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3240   -3.3592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1398   -4.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2848   -5.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0533   -5.5219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6775   -4.9931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5281   -4.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7597   -3.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2616   -4.3577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6707   -3.7931    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0680   -5.1516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8623   -2.6849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.2149   -1.9480    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.0318   -1.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7537   -1.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4198   -2.6932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2331   -2.7188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6658   -2.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2792   -1.3041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4599   -1.2767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4826   -2.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3968   -1.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9812   -2.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1640   -2.6353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4472   -5.2676    0.0000 Cl  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
 17 19  1  0
 17 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
 16 25  1  0
 25 26  1  0
 26 27  1  0
  9 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4445547

   5-(4-Chlorophenyl)-3-[[ethoxy-(4-methylcyclohexyl)phosphoryl]amino]thiophene-2-carboxylic 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: 441.92

Molecular Weight (Monoisotopic): 441.0930

AlogP: 6.99

#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: 4.91

CX LogD: 1.43

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.45

Np Likeness Score: -0.67

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