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552410

Sigma-Aldrich

5-Amino-4-imidazolecarboxamide

95%

Empirical Formula (Hill Notation):
C4H6N4O
CAS Number:
Molecular Weight:
126.12
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

mp

164-170 °C (lit.)

SMILES string

NC(=O)c1nc[nH]c1N

InChI

1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)

InChI key

DVNYTAVYBRSTGK-UHFFFAOYSA-N

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Application

5-Amino-4-imidazolecarboxamide may be used in the synthesis of 4-(N′-benzoylcarbamoyl)amino-5-imidazolecarboxamide and 5-amino-1-β-D-ribosyl-4-imidazolecarboxamide-5′-phosphate (AICAR).

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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Synthesis of guanosine and its derivatives from 5-amino-l-?-D-ribofuranosyl-4-imidazolecarboxamide. III. Formation of a novel cycloimidazole nucleoside and its cleavage reactions.
Okutsu M and Yamazaki A.
Nucleic Acids Research, 3(1), 237-250 (1976)
Preparation of 5-Amino-1-?-ribosyl-4-imidazolecarboxamide-5'-phosphate and N-(5-Amino-1-?-D-ribosyl-4-imidazolecarbonyl)-L-aspartic Acid 5'-Phosphate.
Huang HT.
Biochemistry, 4(1), 58-62 (1965)
James P White et al.
American journal of physiology. Endocrinology and metabolism, 304(10), E1042-E1052 (2013-03-28)
Although catabolic signaling has a well-established role in muscle wasting during cancer cachexia, the suppression of anabolic signaling also warrants further investigation. In cachectic tumor-bearing mice, circulating IL-6 levels are associated with suppressed muscle protein synthesis and mTORC1 signaling. We...
Jang Han Lee et al.
American journal of physiology. Renal physiology, 304(6), F686-F697 (2013-01-18)
The epithelial-mesenchymal transition (EMT) is a novel mechanism that promotes renal fibrosis. Transforming growth factor-β (TGF-β), angiotensin II, aldosterone, high glucose, and urinary albumin are well-known causes of EMT and renal fibrosis. We examined whether and how activation of AMP-activated...
Hiroyasu Hatakeyama et al.
Molecular biology of the cell, 24(6), 809-817 (2013-01-18)
Tbc1d1 is key to skeletal muscle GLUT4 regulation. By using GLUT4 nanometry combined with a cell-based reconstitution model, we uncover a shift in the regulatory mode of Tbc1d1 by showing that Tbc1d1 temporally acquires insulin responsiveness, which triggers GLUT4 trafficking...

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