ID: ALA1090132

Max Phase: Preclinical

Molecular Formula: C18H19N5O4

Molecular Weight: 369.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cn([C@H]2C[C@H](n3cc(-c4ccccc4)nn3)[C@@H](CO)O2)c(=O)[nH]c1=O

Standard InChI:  InChI=1S/C18H19N5O4/c1-11-8-22(18(26)19-17(11)25)16-7-14(15(10-24)27-16)23-9-13(20-21-23)12-5-3-2-4-6-12/h2-6,8-9,14-16,24H,7,10H2,1H3,(H,19,25,26)/t14-,15+,16+/m0/s1

Standard InChI Key:  YIIUPUWFCBAYMU-ARFHVFGLSA-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: 369.38

Molecular Weight (Monoisotopic): 369.1437

AlogP: 0.62

#Rotatable Bonds: 4

Polar Surface Area: 115.03

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.96

CX Basic pKa:

CX LogP: 1.45

CX LogD: 1.45

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.70

Np Likeness Score: -0.34

References

1. Van Poecke S, Negri A, Gago F, Van Daele I, Solaroli N, Karlsson A, Balzarini J, Van Calenbergh S..  (2010)  3'-[4-Aryl-(1,2,3-triazol-1-yl)]-3'-deoxythymidine analogues as potent and selective inhibitors of human mitochondrial thymidine kinase.,  53  (7): [PMID:20218622] [10.1021/jm901532h]

2. Lin J, Roy V, Wang L, You L, Agrofoglio LA, Deville-Bonne D, McBrayer TR, Coats SJ, Schinazi RF, Eriksson S..  (2010)  3'-(1,2,3-Triazol-1-yl)-3'-deoxythymidine analogs as substrates for human and Ureaplasma parvum thymidine kinase for structure-activity investigations.,  18  (9): [PMID:20378362] [10.1016/j.bmc.2010.03.023]

3. Van Poecke S, Munier-Lehmann H, Helynck O, Froeyen M, Van Calenbergh S..  (2011)  Synthesis and inhibitory activity of thymidine analogues targeting Mycobacterium tuberculosis thymidine monophosphate kinase.,  19  (24): [PMID:22061826] [10.1016/j.bmc.2011.10.021]

4. Sirivolu VR, Vernekar SK, Ilina T, Myshakina NS, Parniak MA, Wang Z..  (2013)  Clicking 3'-azidothymidine into novel potent inhibitors of human immunodeficiency virus.,  56  (21): [PMID:24102161] [10.1021/jm401232v]

Source

Source(1):

• Scientific Literature