Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for AICAR (HMDB01517)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:42 -0700
HMDB ID HMDB01517
Secondary Accession Numbers None
Metabolite Identification
Common Name AICAR
Description AICAR also known as ZMP is an analog of AMP that is capable of stimulating AMP-dependent protein kinase activity(AMPK). AICAR is an intermediate in the generation of inosine monophosphate. AICAR is being clinically used to treat and protect against cardiac ischemic injury. AICAR can enter cardiac cells to inhibit adenosine kinase and adenosine deaminase. It enhances the rate of nucleotide re-synthesis increasing adenosine generation from adenosine monophosphate only during conditions of myocardial ischemia. AICAR increases glucose uptake by inducing translocation of GLUT4 and/or by activating the p38 MAPK pathway.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 5'-P-Ribosyl-5-amino-4-imidazole carboxamide
  2. 5'-Phosphoribosyl-5-amino-4-imidazole carboxamide
  3. 5-Amino-4-imidazolecarboxamide ribotide
  4. AICA ribonucleotide
  5. Aminoimidazole carboxamide ribonucleotide
  6. Z-Nucleotide
Chemical Formula C9H15N4O8P
Average Molecular Weight 338.2112
Monoisotopic Molecular Weight 338.062749988
IUPAC Name {[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name [(2R,3S,4R,5R)-5-(5-amino-4-carbamoylimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphonic acid
CAS Registry Number 3031-94-5
SMILES NC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
InChI Identifier InChI=1S/C9H15N4O8P/c10-7-4(8(11)16)12-2-13(7)9-6(15)5(14)3(21-9)1-20-22(17,18)19/h2-3,5-6,9,14-15H,1,10H2,(H2,11,16)(H2,17,18,19)/t3-,5-,6-,9-/m1/s1
InChI Key NOTGFIUVDGNKRI-UUOKFMHZSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Nucleosides, Nucleotides, and Analogues
Class Imidazole Nucleosides and Nucleotides
Sub Class 1-Phosphoribosyl-imidazoles
Other Descriptors
  • 1-Ribosyl-imidazolecarboxamides
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • Aminoimidazole
  • Carboxamide Group
  • Glycosyl Compound
  • Imidazole
  • Imidazolyl Carboxylic Acid Derivative
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Primary Carboxylic Acid Amide
  • Saccharide
  • Secondary Alcohol
Direct Parent 1-Phosphoribosyl-imidazoles
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 2.79 g/L ALOGPS
LogP -2.16 ALOGPS
LogP -4.8 ChemAxon
LogS -2.08 ALOGPS
pKa (strongest acidic) 1.22 ChemAxon
pKa (strongest basic) 4.8 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 203.38 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 69.14 ChemAxon
Polarizability 28.57 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Skeletal Muscle
Pathways
Name SMPDB Link KEGG Link
Purine Metabolism SMP00050 map00230 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01700 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB001213
KNApSAcK ID C00007383 Link_out
Chemspider ID 58620 Link_out
KEGG Compound ID C04677 Link_out
BioCyc ID AICAR Link_out
BiGG ID 44312 Link_out
Wikipedia Link AICA ribonucleotide Link_out
NuGOwiki Link HMDB01517 Link_out
Metagene Link HMDB01517 Link_out
METLIN ID 6294 Link_out
PubChem Compound 65110 Link_out
PDB ID AMZ Link_out
ChEBI ID 18406 Link_out
References
Synthesis Reference Schmitt, Laurent; Caperelli, Carol A. Enantiospecific synthesis of carbocyclic aminoimidazole carboxamide ribonucleotide (C-AICAR), succinoaminoimidazole carboxamide ribonucleotide (C-SAICAR), and a new intermediate for SAICAR analogs. Nucleosides & Nucleotides (1995), 14(9 & 10), 1929-45.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Jakobsen SN, Hardie DG, Morrice N, Tornqvist HE: 5'-AMP-activated protein kinase phosphorylates IRS-1 on Ser-789 in mouse C2C12 myotubes in response to 5-aminoimidazole-4-carboxamide riboside. J Biol Chem. 2001 Dec 14;276(50):46912-6. Epub 2001 Oct 11. Pubmed: 11598104 Link_out
  2. Koistinen HA, Galuska D, Chibalin AV, Yang J, Zierath JR, Holman GD, Wallberg-Henriksson H: 5-amino-imidazole carboxamide riboside increases glucose transport and cell-surface GLUT4 content in skeletal muscle from subjects with type 2 diabetes. Diabetes. 2003 May;52(5):1066-72. Pubmed: 12716734 Link_out
  3. Koistinen HA, Chibalin AV, Zierath JR: Aberrant p38 mitogen-activated protein kinase signalling in skeletal muscle from Type 2 diabetic patients. Diabetologia. 2003 Oct;46(10):1324-8. Epub 2003 Aug 23. Pubmed: 12937895 Link_out
Enzymes
Name: Adenine phosphoribosyltransferase
Reactions:
  • AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate [RN:R00190]
Gene Name: APRT
Uniprot ID: P07741 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Adenylosuccinate lyase
Reactions:
  • (1) N6-(1,2-dicarboxyethyl)AMP = fumarate + AMP [RN:R01083]
  • (2) (S)-2-[5-amino-1-(5-phospho-D-ribosyl)imidazole-4- carboxamido]succinate = fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R04559]
Gene Name: ADSL
Uniprot ID: P30566 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bifunctional purine biosynthesis protein PURH
Reactions:
  • IMP + H2O = 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide [RN:R01127]
Gene Name: ATIC
Uniprot ID: P31939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA