5-Amino-4-imidazolecarboxamide

Name: 5-Amino-4-imidazolecarboxamide
Brand: ALDRICH

95%

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill) :

C₄H₆N₄O

Numéro CAS:

360-97-4

Poids moléculaire :

126.12

NACRES:

NA.22

PubChem Substance ID:

24879267

UNSPSC Code:

12352005

EC Number:

206-641-4

MDL number:

MFCD02181040

Nom du produit

5-Amino-4-imidazolecarboxamide, 95%

InChI key

DVNYTAVYBRSTGK-UHFFFAOYSA-N

InChI

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

SMILES string

NC(=O)c1nc[nH]c1N

assay

95%

form

solid

mp

164-170 °C (lit.)

functional group

amide

Quality Level

100

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Catégories apparentées

Chemical Building Blocks

Heterocyclic Building Blocks

Chemistry & Biochemicals

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).

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Classe de stockage

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Muscle mTORC1 suppression by IL-6 during cancer cachexia: a role for AMPK.

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

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)

Regulatory mode shift of Tbc1d1 is required for acquisition of insulin-responsive GLUT4-trafficking activity.

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

Aminoimidazole carboxamide ribonucleotide (AICAR) inhibits the growth of retinoblastoma in vivo by decreasing angiogenesis and inducing apoptosis.

Sofia Theodoropoulou et al.

PloS one, 8(1), e52852-e52852 (2013-01-10)

5-Aminoimidazole-4-carboxamide-1-β-4-ribofuranoside (AICAR), an analog of AMP is widely used as an activator of AMP-kinase (AMPK), a protein that regulates the responses of the cell to energy change. Recently, we showed that AICAR-induced AMPK activation inhibits the growth of retinoblastoma cells

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