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4-Amino-5-carbamoylimidazole, 4-Aminoimidazole-5-carboxamide, 4-Carbamoyl-5-aminoimidazole, 4-Carboxamido-5-aminoimidazole, 5-Amino-1H-imidazole-4-carboxamide, 5-Amino-1H-imidazole-4-carboxylic acid amide, 5-Amino-3H-imidazole-4-carboxamide
C4H6N4O
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Quality Level
Assay
95%
form
solid
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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Related Categories
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).
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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.
Nucleic Acids Research, 3(1), 237-250 (1976)
Diabetes, 62(6), 1913-1922 (2013-01-26)
Activation of AMP-activated protein kinase (AMPK) signaling reduces hepatic steatosis and hepatic insulin resistance; however, its regulatory mechanisms are not fully understood. In this study, we sought to determine whether vasodilator-stimulated phosphoprotein (VASP) signaling improves lipid metabolism in the liver
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
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
American journal of physiology. Endocrinology and metabolism, 306(9), E1085-E1092 (2014-03-20)
Exercise can effectively ameliorate type 2 diabetes and insulin resistance. Here we show that the mRNA levels of one of peroxisome proliferator-activated receptor (PPAR) family members, PPARγ1, and genes related to energy metabolism, including PPARγ coactivator-1 protein-1α (PGC-1α) and lipoprotein
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