2-amino-3-cyanoquinoxaline-1,4-diium-1,4-bis(olate)

• ChemBase ID: 34372
• Molecular Formular: C9H6N4O2
• Molecular Mass: 202.16954
• Monoisotopic Mass: 202.04907545
• SMILES: c1ccc2c(c1)[n+](c(c([n+]2[O-])N)C#N)[O-]
• Canonical SMILES: N#Cc1[n+]([O-])c2ccccc2[n+](c1N)[O-]
• InChI: InChI=1S/C9H6N4O2/c10-5-8-9(11)13(15)7-4-2-1-3-6(7)12(8)14/h1-4H,11H2
• InChIKey: ZGVCESZATUMTIM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-3-cyanoquinoxaline-1,4-diium-1,4-bis(olate); 3-amino-2-cyanoquinoxaline-1,4-diium-1,4-bis(olate)
• IUPAC Traditional name: 2-amino-3-cyanoquinoxaline-1,4-diium-1,4-bis(olate); 3-amino-2-cyanoquinoxaline-1,4-diium-1,4-bis(olate)
• Synonyms: 3-Aminoquinoxaline-2-carbonitrile 1,4-dioxide; 2-amino-3-cyanoquinoxalinediium-1,4-diolate; KIH-402

Database IDs

• CAS Number: 23190-84-3
• MDL Number: MFCD00102307
• PubChem SID: 160997679
• PubChem CID: 464050

CALCULATED PROPERTIES

• Acid pKa: 14.304611
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -0.17732367
• LogD (pH = 7.4): -0.17732371
• Log P: -0.17732367
• Molar Refractivity: 54.7552 cm^3
• Polarizability: 19.993435 Å^3
• Polar Surface Area: 100.73 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): -2.463

Safety Information

• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Mechanism of Action: Cytotoxic; Radiosensitizer

Product Information

• Purity: 95%
• Application(s): Anticancer

REFERENCES

• 1. Biol.Pharm.Bull. (17, No. 12, 1676-78, 1994) A convenient screening test for hypoxic cell radiosensitizers/cytotoxins.
• 2. Monge A,Martinez-Crespo FJ,Lopez de Cerain A,Palop JA,Narro S,Senador V,Marin A,Sainz Y,Gonzalez M,Hamilton E (1995)
• Hypoxia-selective agents derived from 2-quinoxalinecarbonitrile 1,4-di-N-oxides. 2.
• Journal of medicinal chemistry 38, 4488-94
• 3. Monge A,Palop JA,Lopez de Cerain A,Senador V,Martinez-Crespo FJ,Sainz Y,Narro S,Garcia E,de Miguel C,Gonzalez M (1995)
• Hypoxia-selective agents derived from quinoxaline 1,4-di-N-oxides.
• Journal of medicinal chemistry 38, 1786-92