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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-09-15 18:34:52 UTC
HMDB IDHMDB0001517
Secondary Accession Numbers
  • HMDB01517
Metabolite Identification
Common NameAICAR
DescriptionAICAR, also known as Z-nucleotide or ZMP, belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond. AICAR is a strong basic compound (based on its pKa). AICAR exists in all living species, ranging from bacteria to humans. Within humans, AICAR participates in a number of enzymatic reactions. In particular, fumaric acid and AICAR can be biosynthesized from SAICAR; which is catalyzed by the enzyme adenylosuccinate lyase. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide; which is mediated by the enzyme bifunctional purine biosynthesis protein purh. In humans, AICAR is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, AICAR has been detected, but not quantified in, several different foods, such as cardoons, chayotes, almonds, buffalo currants, and rambutans. This could make AICAR a potential biomarker for the consumption of these foods. AICAR has been used clinically to treat and protect against cardiac ischemic injury. The drug was first used in the 1980s as a method to preserve blood flow to the heart during surgery and is currently of interest as a potential treatment for diabetes by increasing the metabolic activity of tissues by changing the physical composition of muscle. 5-Aminoimidazole-4-carboxamide ribonucleotide is an intermediate in the generation of inosine monophosphate and analog of adenosine monophosphate (AMP) that is capable of stimulating AMP-dependent protein kinase (AMPK) activity.
Structure
Data?1600194892
Synonyms
ValueSource
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamideChEBI
5'-Phospho-ribosyl-5-amino-4-imidazole carboxamideChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxamideChEBI
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamideChEBI
5-Aminoimidazole-4-carboxamide ribotideChEBI
5-Phosphoribosyl-4-carbamoyl-5-aminoimidazoleChEBI
Acadesine 5'-monophosphateChEBI
AICA-RibonucleotideChEBI
5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamideKegg
Acadesine 5'-monophosphoric acidGenerator
5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamideGenerator
5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamideGenerator
5'-p-Ribosyl-5-amino-4-imidazole carboxamideHMDB
5'-Phosphoribosyl-5-amino-4-imidazole carboxamideHMDB
5-Amino-4-imidazolecarboxamide ribotideHMDB
AICA RibonucleotideHMDB
Aminoimidazole carboxamide ribonucleotideHMDB
Z-NucleotideHMDB
4-Carboxy-5-aminoimidazole ribotideHMDB
5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphateHMDB
5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphateHMDB
AICA Ribonucleotide, (D-ribofuranosyl)-isomerHMDB
AICAriboside 5'-monophosphateHMDB
CAIRHMDB
ZMPHMDB
(2R,3S,4R,5R)-5-(4-Carbam0yl-5-aminoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yljmethyl dihydrogen phosphateHMDB
5'-Phospho-beta-D-ribosyl-5-amino-4-imidazolecarboxamideHMDB
5'-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamideHMDB
5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamideHMDB
5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamideHMDB
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamideHMDB
5-Amino-1-(5’-phosphofuranoribosyl)-4-imidazolecarboxamideHMDB
5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5'-phosphateHMDB
5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5'-phosphateHMDB
5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5’-phosphateHMDB
5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphateHMDB
5-Amino-4-imidazolecarboxamide ribonucleoside 5’-monophosphateHMDB
5-Amino-4-imidazolecarboxamide ribonucleotideHMDB
5-Amino-4-imidazolecarboxamide riboside 5'-monophosphateHMDB
5-Amino-4-imidazolecarboxamide riboside 5’-monophosphateHMDB
5-Aminoimidazole-4-carboxamide ribonucleotideHMDB
5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphateHMDB
5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphateHMDB
5’-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamideHMDB
5’-Phosphoribosyl-5-amino-4-imidazolecarboxamideHMDB
AICA RibotideHMDB
AICARHMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate)HMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5'-monophosphate)HMDB
AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate)HMDB
Acadesine 5’-monophosphateHMDB
Aminoimidazolecarboxamide ribonucleotideHMDB
Chemical FormulaC9H15N4O8P
Average Molecular Weight338.2112
Monoisotopic Molecular Weight338.062749988
IUPAC Name{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional Nameaica ribonucleotide
CAS Registry Number3031-94-5
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 KeyNOTGFIUVDGNKRI-UUOKFMHZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-ribosyl-imidazolecarboxamides. These are organic compounds containing the imidazole ring linked to a ribose ring through a 1-2 bond.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassImidazole ribonucleosides and ribonucleotides
Sub Class1-ribosyl-imidazolecarboxamides
Direct Parent1-ribosyl-imidazolecarboxamides
Alternative Parents
Substituents
  • 1-ribosyl-imidazolecarboxamide
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Pentose monosaccharide
  • 2-heteroaryl carboxamide
  • Imidazole-4-carbonyl group
  • Monoalkyl phosphate
  • Aminoimidazole
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Vinylogous amide
  • Tetrahydrofuran
  • Primary carboxylic acid amide
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxamide group
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Amine
  • Organic oxide
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.79 g/LALOGPS
logP-2.2ALOGPS
logP-4.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)4.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area203.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity69.14 m³·mol⁻¹ChemAxon
Polarizability28.57 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9613000000-e58f9c8b6a55e4f5a202Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0axr-6690400000-587ddf1606113df75d2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0009000000-7425edce1492dba01a40Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1019000000-4ca07d05181423b32ed1Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9300000000-5c28ca5957750fa338e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-70e563a806a4c3a55e97Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-74be45171db0b5560214Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-9104000000-230fd9fc88d41766b56eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0119000000-9504e432c77e845f195dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-1921000000-b59f42e588be20adfd16Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-2900000000-4725adb433c2ef4f7e01Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-731f94a980a3ea830720Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-5900000000-e2c302b537e2a87761caSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-2900000000-f0dad518d8c8a1fa40e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-84c17cba09b2fb11b4d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-ebd6a0aeccf60882a9c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-7900000000-674e1cf6f4488a373690Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-9617000000-715abdd95d031de269f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-f3a4c70c454a0da6eb32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3019a28f446b6ae4ee1fSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Saliva
Tissue Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected and Quantified0.441 +/- 0.133 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.504 +/- 0.126 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified0.548 +/- 0.153 uMAdult (>18 years old)Not Specified
Normal
    • Sugimoto et al. (...
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01700
Phenol Explorer Compound IDNot Available
FooDB IDFDB030675
KNApSAcK IDC00007383
Chemspider ID58620
KEGG Compound IDC04677
BioCyc IDAICAR
BiGG ID44312
Wikipedia LinkAICA_ribonucleotide
METLIN ID6294
PubChem Compound65110
PDB IDNot Available
ChEBI ID18406
Food Biomarker OntologyNot Available
VMH IDAICAR
MarkerDB ID
References
Synthesis ReferenceSchmitt, 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 ]
  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 ]
  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 ]

Enzymes

General function:
Involved in adenine phosphoribosyltransferase activity
Specific function:
Catalyzes a salvage reaction resulting in the formation of AMP, that is energically less costly than de novo synthesis.
Gene Name:
APRT
Uniprot ID:
P07741
Molecular weight:
19607.535
Reactions
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
Reactions
SAICAR → Fumaric acid + AICARdetails
SAICAR → Fumaric acid + AICARdetails
General function:
Involved in IMP cyclohydrolase activity
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
P31939
Molecular weight:
64615.255
Reactions
10-Formyltetrahydrofolate + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]