ID: ALA292278

Max Phase: Preclinical

Molecular Formula: C8H10N2O5

Molecular Weight: 214.18

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1ccn([C@H]2CO[C@@H](CO)O2)c(=O)[nH]1

Standard InChI:  InChI=1S/C8H10N2O5/c11-3-7-14-4-6(15-7)10-2-1-5(12)9-8(10)13/h1-2,6-7,11H,3-4H2,(H,9,12,13)/t6-,7-/m1/s1

Standard InChI Key:  MYQDAUKUBLHXLX-RNFRBKRXSA-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: 214.18

Molecular Weight (Monoisotopic): 214.0590

AlogP: -1.60

#Rotatable Bonds: 2

Polar Surface Area: 93.55

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.70

CX Basic pKa:

CX LogP: -0.94

CX LogD: -0.94

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.62

Np Likeness Score: 0.73

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. Kim HO, Ahn SK, Alves AJ, Beach JW, Jeong LS, Choi BG, Van Roey P, Schinazi RF, Chu CK..  (1992)  Asymmetric synthesis of 1,3-dioxolane-pyrimidine nucleosides and their anti-HIV activity.,  35  (11): [PMID:1597854] [10.1021/jm00089a007]

3. 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]

4. Lin JS, Kira T, Gullen E, Choi Y, Qu F, Chu CK, Cheng YC..  (1999)  Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.,  42  (12): [PMID:10377226] [10.1021/jm9806749]

Source

Source(1):

• Scientific Literature