5-amino-1H-imidazole-4-carboxamide

• ChemBase ID: 68657
• Molecular Formular: C4H6N4O
• Molecular Mass: 126.11664
• Monoisotopic Mass: 126.05416083
• SMILES: c1nc(c([nH]1)N)C(=O)N
• Canonical SMILES: NC(=O)c1nc[nH]c1N
• InChI: InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
• InChIKey: DVNYTAVYBRSTGK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1H-imidazole-4-carboxamide; 4-amino-1H-imidazole-5-carboxamide
• IUPAC Traditional name: 4-aminoimidazole-5-carboxamide; 5-aminoimidazole-4-carboxamide; 4-amino-5-imidazolecarboxamide
• Synonyms: AICA; 4-Amino-5-carbamoylimidazole; 5-Aminoimidazole-4-carboxamide; AIC; Ba 2756; NSC 7784; 5-Aminoimidazole-4-carboxamide; 5-Amino-4-imidazolecarboxamide; 5-Amino-1H-imidazole-4-carboxamide; 4-Amino-1H-imidazole-5-carboxamide; 4-Amino-1H-imidazole-5-carboxamide; 4-amino-5-imidazolecarboxamide; 5-amino-4-imidazolecarboxamide; 5-氨基咪唑-4-甲酰胺

Database IDs

• CAS Number: 360-97-4; 21299-72-9
• EC Number: 206-641-4
• MDL Number: MFCD00044596; MFCD02181040
• PubChem SID: 24879267; 162034387
• PubChem CID: 9679

CALCULATED PROPERTIES

• Acid pKa: 10.471152
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -1.1780831
• LogD (pH = 7.4): -1.0016403
• Log P: -0.99836856
• Molar Refractivity: 31.6729 cm^3
• Polarizability: 11.237611 Å^3
• Polar Surface Area: 97.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 164-170 °C(lit.); 170-172°C (dec.); 249 - 251°C
• Hydrophobicity(logP): -0.555

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: NI3910000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 95+%; 98%
• Empirical Formula (Hill Notation): C4H6N4O

DETAILS

Sigma Aldrich - 552410

Packaging
25 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 552410.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - A611690

A metabolite of Temozolomide.

REFERENCES

• Jaeken, J., et al.: Lancet, 2, 1058 (1984)
• Baggott, J., et al.: Biochem. J., 236, 193 (1984)
• Baggott, J., et al.: Arch. Dermatol., 135, 813 (1984)