beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine diphosphate

ID: ALA556224

Chembl Id: CHEMBL556224

PubChem CID: 23725127

Max Phase: Preclinical

Molecular Formula: C10H15FN2O11P2

Molecular Weight: 420.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@@]1(F)[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O)O[C@H]1n1ccc(=O)[nH]c1=O

Standard InChI:  InChI=1S/C10H15FN2O11P2/c1-10(11)7(15)5(4-22-26(20,21)24-25(17,18)19)23-8(10)13-3-2-6(14)12-9(13)16/h2-3,5,7-8,15H,4H2,1H3,(H,20,21)(H,12,14,16)(H2,17,18,19)/t5-,7-,8-,10-/m1/s1

Standard InChI Key:  VPPLCOBQDZAMRD-VPCXQMTMSA-N

Alternative Forms

1. Parent:

   

   ALA556224

   2'-Deoxy-2'-Fluoro-2'-Methyluridine 5'-(Trihydrogen Diphosphate)

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: 420.18

Molecular Weight (Monoisotopic): 420.0135

AlogP: -1.25

#Rotatable Bonds: 6

Polar Surface Area: 197.61

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 1.77

CX Basic pKa: ┄

CX LogP: -1.79

CX LogD: -6.82

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.34

Np Likeness Score: 1.11

References

1. Murakami E, Niu C, Bao H, Micolochick Steuer HM, Whitaker T, Nachman T, Sofia MA, Wang P, Otto MJ, Furman PA..  (2008)  The mechanism of action of beta-D-2'-deoxy-2'-fluoro-2'-C-methylcytidine involves a second metabolic pathway leading to beta-D-2'-deoxy-2'-fluoro-2'-C-methyluridine 5'-triphosphate, a potent inhibitor of the hepatitis C virus RNA-dependent RNA polymerase.,  52  (2): [PMID:17999967] [10.1128/aac.01184-07]

Source

Source(1):

• Scientific Literature