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

ID: ALA4552559

PubChem CID: 68073121

Max Phase: Preclinical

Molecular Formula: C20H26NO4PS

Molecular Weight: 407.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOP(=O)(Nc1cc(-c2ccccc2)sc1C(=O)O)C1CCC(C)CC1

Standard InChI:  InChI=1S/C20H26NO4PS/c1-3-25-26(24,16-11-9-14(2)10-12-16)21-17-13-18(27-19(17)20(22)23)15-7-5-4-6-8-15/h4-8,13-14,16H,3,9-12H2,1-2H3,(H,21,24)(H,22,23)

Standard InChI Key:  PERWXTGSISIBKA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   15.2451   -4.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8923   -4.7951    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5680   -4.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3372   -3.5486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5211   -3.5284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3370   -4.6101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4819   -5.4155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2504   -5.6911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8747   -5.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7252   -4.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9568   -4.0828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4587   -4.5269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8678   -3.9623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2652   -5.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0594   -2.8541    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4121   -2.1173    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   16.2289   -2.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9508   -1.4429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6170   -2.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4302   -2.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8629   -2.1944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4763   -1.4734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6570   -1.4459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6797   -2.2212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5939   -2.1090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1783   -2.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3611   -2.8045    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
 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
M  END

Alternative Forms

1. Parent:

   

   ALA4552559

   3-[[Ethoxy-(4-methylcyclohexyl)phosphoryl]amino]-5-phenylthiophene-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: 407.47

Molecular Weight (Monoisotopic): 407.1320

AlogP: 6.33

#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: 4.35

CX LogD: 0.86

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.52

Np Likeness Score: -0.51

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