ID: ALA222630

Max Phase: Preclinical

Molecular Formula: C10H15FN3O7P

Molecular Weight: 339.22

Molecule Type: Small molecule

Representations

Canonical SMILES:  C[C@@]1(F)[C@H](O)[C@@H](COP(=O)(O)O)O[C@H]1n1ccc(N)nc1=O

Standard InChI:  InChI=1S/C10H15FN3O7P/c1-10(11)7(15)5(4-20-22(17,18)19)21-8(10)14-3-2-6(12)13-9(14)16/h2-3,5,7-8,15H,4H2,1H3,(H2,12,13,16)(H2,17,18,19)/t5-,7-,8-,10-/m1/s1

Standard InChI Key:  MJKXCSWNCSKTGP-VPCXQMTMSA-N

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

Properties

Molecular Weight: 339.22

Molecular Weight (Monoisotopic): 339.0632

AlogP: -1.08

#Rotatable Bonds: 4

Polar Surface Area: 157.13

Molecular Species: ACID

HBA: 8

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 1.22

CX Basic pKa:

CX LogP: -1.75

CX LogD: -5.28

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.50

Np Likeness Score: 1.13

References

1. Murakami E, Bao H, Ramesh M, McBrayer TR, Whitaker T, Micolochick Steuer HM, Schinazi RF, Stuyver LJ, Obikhod A, Otto MJ, Furman PA..  (2007)  Mechanism of activation of beta-D-2'-deoxy-2'-fluoro-2'-c-methylcytidine and inhibition of hepatitis C virus NS5B RNA polymerase.,  51  (2): [PMID:17101674] [10.1128/aac.00400-06]

2. 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]

3. Murakami E, Bao H, Mosley RT, Du J, Sofia MJ, Furman PA..  (2011)  Adenosine deaminase-like protein 1 (ADAL1): characterization and substrate specificity in the hydrolysis of N(6)- or O(6)-substituted purine or 2-aminopurine nucleoside monophosphates.,  54  (16): [PMID:21755941] [10.1021/jm200650j]

Source

Source(1):

• Scientific Literature