3-Hydroxy-2,2-dimethyl-thiopropionic acid S-{2-[(2R,4aR,6R,7R,7aR)-7-chloro-6-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-methyl-2-oxo-tetrahydro-2lambda5-furo[3,2-d][1,3,2]dioxaphosphinin-2-yloxy]-ethyl}ester

ID: ALA4098752

PubChem CID: 118966242

Max Phase: Preclinical

Molecular Formula: C17H24ClN2O9PS

Molecular Weight: 498.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(CO)C(=O)SCCO[P@]1(=O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@](C)(Cl)[C@@H]2O1

Standard InChI:  InChI=1S/C17H24ClN2O9PS/c1-16(2,9-21)14(23)31-7-6-26-30(25)27-8-10-12(29-30)17(3,18)13(28-10)20-5-4-11(22)19-15(20)24/h4-5,10,12-13,21H,6-9H2,1-3H3,(H,19,22,24)/t10-,12-,13-,17-,30-/m1/s1

Standard InChI Key:  VVNGSOYNBKTUIX-QFDWMXEGSA-N

Molfile:  

     RDKit          2D

 33 35  0  0  0  0  0  0  0  0999 V2000
    5.9556  -10.6194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683   -9.9136    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.5507   -9.9091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2606  -10.5479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5698  -10.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5471  -10.9360    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.0291   -9.4330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5559   -8.8002    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8492   -9.4103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2840  -10.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1028  -10.0838    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4854   -9.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0559   -8.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2426   -8.6922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8972  -10.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.3056   -9.3409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7906   -9.8971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7805   -9.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0669   -8.6707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586   -9.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870  -10.3177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7840  -10.7102    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7757   -8.2545    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1461   -9.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3289   -9.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243   -8.4846    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.1071   -8.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -9.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7024   -7.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8774   -9.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992   -9.8954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2782   -9.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4727   -8.4709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  1  6
  5  4  1  0
  5  6  1  6
 17  5  1  0
  5  7  1  0
 18  8  1  0
  7  8  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  7  9  1  1
 10 15  2  0
 12 16  2  0
 17 18  1  0
 17 21  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  2 21  1  0
 17 22  1  1
 18 23  1  6
  3 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 28 31  1  0
 28 32  1  0
 30 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4098752

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 498.88

Molecular Weight (Monoisotopic): 498.0629

AlogP: 1.25

#Rotatable Bonds: 7

Polar Surface Area: 146.15

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.85

CX Basic pKa: ┄

CX LogP: 1.14

CX LogD: 1.13

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.32

Np Likeness Score: 0.52

References

1. Alexandre FR, Badaroux E, Bilello JP, Bot S, Bouisset T, Brandt G, Cappelle S, Chapron C, Chaves D, Convard T, Counor C, Da Costa D, Dukhan D, Gay M, Gosselin G, Griffon JF, Gupta K, Hernandez-Santiago B, La Colla M, Lioure MP, Milhau J, Paparin JL, Peyronnet J, Parsy C, Pierra Rouvière C, Rahali H, Rahali R, Salanson A, Seifer M, Serra I, Standring D, Surleraux D, Dousson CB..  (2017)  The discovery of IDX21437: Design, synthesis and antiviral evaluation of 2'-α-chloro-2'-β-C-methyl branched uridine pronucleotides as potent liver-targeted HCV polymerase inhibitors.,  27  (18): [PMID:28835346] [10.1016/j.bmcl.2017.08.029]

Source

Source(1):

• Scientific Literature