Basic information
- CAS
3031-94-5- Standard SMILES
NC(=O)c1ncn([C@@H]2O[C@H](COP(=O)(O)O)[C@@H](O)[C@H]2O)c1N- InChIKey
NOTGFIUVDGNKRI-UUOKFMHZSA-N- Molecular formula
- C9H15N4O8P
- Average molar mass
- 338.21 g/mol
- Monoisotopic mass
- 338.06275045
Overview
AICA ribonucleotide is a 1-(phosphoribosyl)imidazolecarboxamide that is acadesine in which the hydroxy group at the 5' position has been converted to its monophosphate derivative. It has a role as a cardiovascular drug, a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite and a human metabolite. It is an aminoimidazole and a 1-(phosphoribosyl)imidazolecarboxamide. It is functionally related to an acadesine. It is a conjugate acid of a 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide(2-).
Names & identifiers
- Preferred name
- AICA Ribotide
- IUPAC
- [(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
- English name
- 5'-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate
- Molecular formula
- C9H15N4O8P
- Molecular weight
- 338.21
Names & synonyms
AICA ribonucleotide3031-94-5Z-nucleotideAICA-ribonucleotideaminoimidazole carboxamide ribonucleotide5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide5-amino-4-imidazolecarboxamide ribotideAcadesine 5'-monophosphate5-Aminoimidazole-4-carboxamide ribotideAICA RibotideF0X88YW0YK5-Amino-4-imidazole carboxamide ribonucleotide
Show more names
ZMP5-AMINOIMIDAZOLE-4-CARBOXAMIDE-1-BETA-D-RIBOFURANOSYL 5'-MONOPHOSPHATEAICA-Riboside, 5′-PhosphateNSC 283955NSC 292227AICAR-5'-MPAcaribonucleotideAICAR-5'-MP / ZMPAICAR-5′,-MP
5-Phosphoribosyl-4-carbamoyl-5-aminoimidazole5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphateNSC-283955NSC-2922275'-Phospho-ribosyl-5-amino-4-imidazole carboxamideCHEBI:18406Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosyl-, 5'-(dihydrogen phosphate){[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Properties
Computed structural properties
- XLogP
- -3.8
- Topological polar surface area
- 203 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 475
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical DescriptionSolid
Collision Cross Section
171.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
170.5 Ų [M-H]-
Physicochemical properties
- Melting point
- 198 · 198-202°C dec.
- Boiling point
- 845.3 · 845.3±75.0 °C(Predicted)
- Density
- 2.3 · 2.30±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO (Slightly, Heated, Sonicated), Methanol (Slightly), Water (Slightly)
- form
- White to light pink solid
- pka
- 1.86 · 1.86±0.10(Predicted)
- color
- White to Pink
- optical activity
- -69 · [α]/D -69.0±3.0°, c = 0.1 in sodium bicarbonate
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29349990
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Tissue LocationsSkeletal Muscle
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)
Applications
UsesAICAR monophosphate is a 5′′-phosphorylated analog of cell permeable AICAR that mimics AMP. AICAR is an adenosine monophophate (AMP)-activated protein kinase (AMPK) activator/agonist.
General Description5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5′-monophosphate (AICAR monophosphate) is an intermediate metabolite in the purine de novo synthesis pathway and a potent activator of the human AMP-activated protein kinase (AMPK) activity in vitro. It can play an important regulatory role.
Suppliers49 total
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
Related reactions
2 records
Compound notes
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