ID: ALA573289

Max Phase: Preclinical

Molecular Formula: C11H13N3O5

Molecular Weight: 267.24

Molecule Type: Small molecule

Representations

Canonical SMILES:  C#Cc1c(C(N)=O)ncn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C11H13N3O5/c1-2-5-7(10(12)18)13-4-14(5)11-9(17)8(16)6(3-15)19-11/h1,4,6,8-9,11,15-17H,3H2,(H2,12,18)/t6-,8-,9-,11-/m1/s1

Standard InChI Key:  SWQQELWGJDXCFT-PNHWDRBUSA-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: 267.24

Molecular Weight (Monoisotopic): 267.0855

AlogP: -2.43

#Rotatable Bonds: 3

Polar Surface Area: 130.83

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.42

CX Basic pKa: 3.12

CX LogP: -2.40

CX LogD: -2.40

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.45

Np Likeness Score: 0.80

References

1. Minakawa N, Takeda T, Sasaki T, Matsuda A, Ueda T..  (1991)  Nucleosides and nucleotides. 96. Synthesis and antitumor activity of 5-ethynyl-1-beta-D-ribofuranosylimidazole-4-carboxamide (EICAR) and its derivatives.,  34  (2): [PMID:1995901] [10.1021/jm00106a045]

2. Stevens AJ, Gahan ME, Mahalingam S, Keller PA..  (2009)  The medicinal chemistry of dengue fever.,  52  (24): [PMID:19739651] [10.1021/jm900652e]

3. Okano Y, Saito-Tarashima N, Kurosawa M, Iwabu A, Ota M, Watanabe T, Kato F, Hishiki T, Fujimuro M, Minakawa N..  (2019)  Synthesis and biological evaluation of novel imidazole nucleosides as potential anti-dengue virus agents.,  27  (11): [PMID:31003866] [10.1016/j.bmc.2019.04.015]

4. Nascimento IJDS, Santos-Júnior PFDS, Aquino TM, Araújo-Júnior JX, Silva-Júnior EFD..  (2021)  Insights on Dengue and Zika NS5 RNA-dependent RNA polymerase (RdRp) inhibitors.,  224  [PMID:34274831] [10.1016/j.ejmech.2021.113698]

Source

Source(1):

• Scientific Literature