ID: ALA591804

Max Phase: Phase

Molecular Formula: C9H11N5O4

Molecular Weight: 253.22

Molecule Type: Small molecule

Representations

Synonyms (4): Azddu | Navuridine | CS-87 | NSC-380882
Synonyms from Alternative Forms(4):

Canonical SMILES:  [N-]=[N+]=N[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO

Standard InChI:  InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6+,8+/m0/s1

Standard InChI Key:  ZSNNBSPEFVIUDS-SHYZEUOFSA-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: Yes

Availability: No

Prodrug: No

Properties

Molecular Weight: 253.22

Molecular Weight (Monoisotopic): 253.0811

AlogP: -0.50

#Rotatable Bonds: 3

Polar Surface Area: 133.08

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.71

CX Basic pKa:

CX LogP: -0.69

CX LogD: -0.81

Aromatic Rings: 1

Heavy Atoms: 18

QED Weighted: 0.43

Np Likeness Score: 1.07

References

1. Lin TS, Gao YS, Mancini WR..  (1983)  Synthesis and biological activity of various 3'-azido and 3'-amino analogues of 5-substituted pyrimidine deoxyribonucleosides.,  26  (12): [PMID:6644738] [10.1021/jm00366a006]

2. Hong CI, Nechaev A, Kirisits AJ, Vig R, West CR, Manouilov KK, Chu CK..  (1996)  Nucleoside conjugates. 15. Synthesis and biological activity of anti-HIV nucleoside conjugates of ether and thioether phospholipids.,  39  (9): [PMID:8627600] [10.1021/jm950620o]

3. Van Aerschot A, Everaert D, Balzarini J, Augustyns K, Jie L, Janssen G, Peeters O, Blaton N, De Ranter C, De Clercq E..  (1990)  Synthesis and anti-HIV evaluation of 2',3'-dideoxyribo-5-chloropyrimidine analogues: reduced toxicity of 5-chlorinated 2',3'-dideoxynucleosides.,  33  (6): [PMID:2342078] [10.1021/jm00168a046]

4. Lin TS, Shen ZY, August EM, Brankovan V, Yang H, Ghazzouli I, Prusoff WH..  (1989)  Synthesis and antiviral activity of several 2,5'-anhydro analogues of 3'-azido-3'-deoxythymidine, 3'-azido-2',3'-dideoxyuridine, 3'-azido-2',3'-dideoxy-5-halouridines, and 3'-deoxythymidine against human immunodeficiency virus and Rauscher-murine leukemia virus.,  32  (8): [PMID:2754712] [10.1021/jm00128a034]

5. Herdewijn P, Balzarini J, Baba M, Pauwels R, Van Aerschot A, Janssen G, De Clercq E..  (1988)  Synthesis and anti-HIV activity of different sugar-modified pyrimidine and purine nucleosides.,  31  (10): [PMID:3172142] [10.1021/jm00118a033]

6. Chu CK, Bhadti VS, Doshi KJ, Etse JT, Gallo JM, Boudinot FD, Schinazi RF..  (1990)  Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.,  33  (8): [PMID:2374145] [10.1021/jm00170a023]

7. Chu CK, Bhadti VS, Doshi KJ, Etse JT, Gallo JM, Boudinot FD, Schinazi RF..  (1990)  Brain targeting of anti-HIV nucleosides: synthesis and in vitro and in vivo studies of dihydropyridine derivatives of 3'-azido-2',3'-dideoxyuridine and 3'-azido-3'-deoxythymidine.,  33  (8): [PMID:2374145] [10.1021/jm00170a023]

8. Lin TS, Guo JY, Schinazi RF, Chu CK, Xiang JN, Prusoff WH..  (1988)  Synthesis and antiviral activity of various 3'-azido analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV).,  31  (2): [PMID:3339606] [10.1021/jm00397a011]

9. Lin TS, Chen MS, McLaren C, Gao YS, Ghazzouli I, Prusoff WH..  (1987)  Synthesis and antiviral activity of various 3'-azido, 3'-amino, 2',3'-unsaturated, and 2',3'-dideoxy analogues of pyrimidine deoxyribonucleosides against retroviruses.,  30  (2): [PMID:3643284] [10.1021/jm00385a033]

10. Lin TS, Mancini WR..  (1983)  Synthesis and antineoplastic activity of 3'-azido and 3'-amino analogues of pyrimidine deoxyribonucleoside.,  26  (4): [PMID:6834387] [10.1021/jm00358a016]

11. Chu CK, Schinazi RF, Ahn MK, Ullas GV, Gu ZP..  (1989)  Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells.,  32  (3): [PMID:2918508] [10.1021/jm00123a018]

12. Zhang HW, Coats SJ, Bondada L, Amblard F, Detorio M, Asif G, Fromentin E, Solomon S, Obikhod A, Whitaker T, Sluis-Cremer N, Mellors JW, Schinazi RF..  (2010)  Synthesis and evaluation of 3'-azido-2',3'-dideoxypurine nucleosides as inhibitors of human immunodeficiency virus.,  20  (1): [PMID:19948402] [10.1016/j.bmcl.2009.11.031]

13. PubChem BioAssay data set, 

14. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

15. Johannes Zuegg, Alysha Elliott, Maite Amado, Emma Cowie, Ali Hinton, Geraldine Kaeslin, Angela Kavanagh, Anne Kunert, Gabriell Lowe, Soumya Ramu, Janet Reid, Robin Trauer, Mathilde Desselle, Ruth Neale, Karl Hansford, Mark Blascovich, Matthew Cooper. CO-ADD screening of MMV (CH) - Pandemic Response Box,  [10.6019/CHEMBL4513161]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names
• CO-ADD antimicrobial screening data