ID: ALA303553

Max Phase: Preclinical

Molecular Formula: C8H9BrN2O5

Molecular Weight: 293.07

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=c1[nH]c(=O)n([C@H]2CO[C@@H](CO)O2)cc1Br

Standard InChI:  InChI=1S/C8H9BrN2O5/c9-4-1-11(8(14)10-7(4)13)5-3-15-6(2-12)16-5/h1,5-6,12H,2-3H2,(H,10,13,14)/t5-,6-/m1/s1

Standard InChI Key:  PLHVEYZUKLKVIO-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: 293.07

Molecular Weight (Monoisotopic): 291.9695

AlogP: -0.84

#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: 8.44

CX Basic pKa:

CX LogP: -0.11

CX LogD: -0.15

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.74

Np Likeness Score: 0.36

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