ID: ALA283403

Max Phase: Phase

Molecular Formula: C17H18N4O3S

Molecular Weight: 358.42

Molecule Type: Small molecule

Representations

Synonyms (5): Viroxime component b | Zinviroxime | LY 122772 | LY-122772 | NSC-346230
Synonyms from Alternative Forms(5):

Canonical SMILES:  CC(C)S(=O)(=O)n1c(N)nc2ccc(/C(=N/O)c3ccccc3)cc21

Standard InChI:  InChI=1S/C17H18N4O3S/c1-11(2)25(23,24)21-15-10-13(8-9-14(15)19-17(21)18)16(20-22)12-6-4-3-5-7-12/h3-11,22H,1-2H3,(H2,18,19)/b20-16+

Standard InChI Key:  IWKXBHQELWQLHF-CAPFRKAQSA-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: 358.42

Molecular Weight (Monoisotopic): 358.1100

AlogP: 2.43

#Rotatable Bonds: 4

Polar Surface Area: 110.57

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 6.69

CX Basic pKa: 4.40

CX LogP: 2.48

CX LogD: 1.69

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.42

Np Likeness Score: -0.76

References

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2. Victor F, Brown TJ, Campanale K, Heinz BA, Shipley LA, Su KS, Tang J, Vance LM, Spitzer WA..  (1997)  Synthesis, antiviral activity, and biological properties of vinylacetylene analogs of enviroxime.,  40  (10): [PMID:9154972] [10.1021/jm960718i]

3. Kelley JL, Linn JA, Krochmal MP, Selway JW..  (1988)  9-Benzyl-6-(dimethylamino)-9H-purines with antirhinovirus activity.,  31  (10): [PMID:2845083] [10.1021/jm00118a025]

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6. Wikel JH, Paget CJ, DeLong DC, Nelson JD, Wu CY, Paschal JW, Dinner A, Templeton RJ, Chaney MO, Jones ND, Chamberlin JW..  (1980)  Synthesis of syn and anti isomers of 6-[[(hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-benzimidazol-2-amine. Inhibitors of rhinovirus multiplication.,  23  (4): [PMID:6247489] [10.1021/jm00178a004]

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11. De Palma AM, Thibaut HJ, van der Linden L, Lanke K, Heggermont W, Ireland S, Andrews R, Arimilli M, Al-Tel TH, De Clercq E, van Kuppeveld F, Neyts J..  (2009)  Mutations in the nonstructural protein 3A confer resistance to the novel enterovirus replication inhibitor TTP-8307.,  53  (5): [PMID:19237651] [10.1128/aac.00934-08]

12. Aguado L, Canela MD, Thibaut HJ, Priego EM, Camarasa MJ, Leyssen P, Neyts J, Pérez-Pérez MJ..  (2012)  Efficient synthesis and anti-enteroviral activity of 9-arylpurines.,  49  [PMID:22305341] [10.1016/j.ejmech.2012.01.022]

13. PubChem BioAssay data set, 

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

15. Han X, Sun N, Wu H, Guo D, Tien P, Dong C, Wu S, Zhou HB..  (2016)  Identification and Structure-Activity Relationships of Diarylhydrazides as Novel Potent and Selective Human Enterovirus Inhibitors.,  59  (5): [PMID:26885567] [10.1021/acs.jmedchem.5b01803]

16. Tosh DK,Toti KS,Hurst BL,Julander JG,Jacobson KA.  (2020)  Structure activity relationship of novel antiviral nucleosides against Enterovirus A71.,  30  (23): [PMID:33031923] [10.1016/j.bmcl.2020.127599]

17. Tang Q,Xu Z,Jin M,Shu T,Chen Y,Feng L,Zhang Q,Lan K,Wu S,Zhou HB.  (2020)  Identification of dibucaine derivatives as novel potent enterovirus 2C helicase inhibitors: In vitro, in vivo, and combination therapy study.,  202  [PMID:32619885] [10.1016/j.ejmech.2020.112310]

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Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• USP Dictionary of USAN and International Drug Names