5-(4-(benzo[b]thiophen-2-yl)phenyl)-3-((2,4-dimethylphenyl)(methoxy)phosphorylamino)thiophene-2-carboxylic acid

ID: ALA4522572

PubChem CID: 59481576

Max Phase: Preclinical

Molecular Formula: C28H24NO4PS2

Molecular Weight: 533.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COP(=O)(Nc1cc(-c2ccc(-c3cc4ccccc4s3)cc2)sc1C(=O)O)c1ccc(C)cc1C

Standard InChI:  InChI=1S/C28H24NO4PS2/c1-17-8-13-23(18(2)14-17)34(32,33-3)29-22-16-26(36-27(22)28(30)31)20-11-9-19(10-12-20)25-15-21-6-4-5-7-24(21)35-25/h4-16H,1-3H3,(H,29,32)(H,30,31)

Standard InChI Key:  YGCOTKJJIYKCSF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 36 40  0  0  0  0  0  0  0  0999 V2000
    1.9307   -4.4613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5779   -4.9602    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.2535   -4.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0228   -3.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2067   -3.6935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0225   -4.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1675   -5.5806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9360   -5.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5602   -5.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4108   -4.5197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6424   -4.2479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442   -4.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5534   -4.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9507   -5.4859    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7450   -3.0192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976   -2.2823    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.9145   -2.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6363   -1.6080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2794   -2.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2984   -3.0252    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1145   -3.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5443   -2.3532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1521   -1.6314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3373   -1.6109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3612   -2.3758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9458   -0.8936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8780   -1.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3299   -5.6019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5607   -6.3825    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.0048   -5.1371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6521   -5.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3776   -6.4036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9048   -7.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7064   -6.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9782   -6.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4492   -5.4879    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
 17 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 17  1  0
 22 25  1  0
 24 26  1  0
 19 27  1  0
  9 28  1  0
 28 29  1  0
 29 32  1  0
 31 30  1  0
 30 28  2  0
 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 35  1  0
 35 36  2  0
 36 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4522572

   5-[4-(1-Benzothiophen-2-yl)phenyl]-3-[[(2,4-dimethylphenyl)-methoxyphosphoryl]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: 533.61

Molecular Weight (Monoisotopic): 533.0884

AlogP: 8.19

#Rotatable Bonds: 7

Polar Surface Area: 75.63

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.26

CX Basic pKa: ┄

CX LogP: 6.85

CX LogD: 3.29

Aromatic Rings: 5

Heavy Atoms: 36

QED Weighted: 0.21

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