ID: ALA505733

Max Phase: Preclinical

Molecular Formula: C8H10FN3O4

Molecular Weight: 231.18

Molecule Type: Small molecule

Representations

Canonical SMILES:  Nc1nc(=O)n([C@H]2CO[C@@H](CO)O2)cc1F

Standard InChI:  InChI=1S/C8H10FN3O4/c9-4-1-12(8(14)11-7(4)10)5-3-15-6(2-13)16-5/h1,5-6,13H,2-3H2,(H2,10,11,14)/t5-,6-/m1/s1

Standard InChI Key:  RJKXXGNCKMQXTH-PHDIDXHHSA-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: 231.18

Molecular Weight (Monoisotopic): 231.0655

AlogP: -1.17

#Rotatable Bonds: 2

Polar Surface Area: 99.60

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.85

CX Basic pKa:

CX LogP: -1.12

CX LogD: -1.12

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.66

Np Likeness Score: 0.28

References

1. Wilson LJ, Choi W, Spurling T, Liotta DC, Schinazi RF, Cannon D, Painter GR, St. Clair M, Furman PA.  (1993)  The synthesis and anti-hiv activity of pyrimidine dioxolanyl nucleosides,  3  (2): [10.1016/S0960-894X(01)80870-2]

2. Wilson LJ, Choi W, Spurling T, Liotta DC, Schinazi RF, Cannon D, Painter GR, St. Clair M, Furman PA.  (1993)  The synthesis and anti-hiv activity of pyrimidine dioxolanyl nucleosides,  3  (2): [10.1016/S0960-894X(01)80870-2]

3. Wilson LJ, Choi W, Spurling T, Liotta DC, Schinazi RF, Cannon D, Painter GR, St. Clair M, Furman PA.  (1993)  The synthesis and anti-hiv activity of pyrimidine dioxolanyl nucleosides,  3  (2): [10.1016/S0960-894X(01)80870-2]

4. Lee M, Chu CK, Balakrishna Pai S, Zhu Y, Cheng Y, Chun MW, Chung WK.  (1995)  Dioxolane cytosine nucleosides as anti-hepatitis B agents,  5  (17): [10.1016/0960-894X(95)00343-R]

5. Lee M, Chu CK, Balakrishna Pai S, Zhu Y, Cheng Y, Chun MW, Chung WK.  (1995)  Dioxolane cytosine nucleosides as anti-hepatitis B agents,  5  (17): [10.1016/0960-894X(95)00343-R]

6. Lee M, Chu CK, Balakrishna Pai S, Zhu Y, Cheng Y, Chun MW, Chung WK.  (1995)  Dioxolane cytosine nucleosides as anti-hepatitis B agents,  5  (17): [10.1016/0960-894X(95)00343-R]

7. Mao S, Bouygues M, Welch C, Biba M, Chilenski J, Schinazi RF, Liotta DC..  (2004)  Synthesis of enantiomerically pure D-FDOC, an anti-HIV agent.,  14  (19): [PMID:15341966] [10.1016/j.bmcl.2004.07.016]

8. Mao S, Bouygues M, Welch C, Biba M, Chilenski J, Schinazi RF, Liotta DC..  (2004)  Synthesis of enantiomerically pure D-FDOC, an anti-HIV agent.,  14  (19): [PMID:15341966] [10.1016/j.bmcl.2004.07.016]

9. Asif G, Hurwitz SJ, Obikhod A, Delinsky D, Narayanasamy J, Chu CK, McClure HM, Schinazi RF..  (2007)  Pharmacokinetics of the anti-human immunodeficiency virus agent 1-(beta-D-dioxolane)thymine in rhesus monkeys.,  51  (7): [PMID:17485498] [10.1128/aac.01498-06]

Source

Source(1):

• Scientific Literature