Showing metabocard for AICAR (BMDB0001517)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:05 UTC
Update Date2020-05-21 16:27:08 UTC
BMDB IDBMDB0001517
Secondary Accession Numbers
  • BMDB01517
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 cattle, AICAR participates in a number of enzymatic reactions. In particular, fumaric acid and AICAR can be biosynthesized from SAICAR through the action of the enzyme adenylosuccinate lyase. In addition, 10-formyltetrahydrofolate and AICAR can be converted into tetrahydrofolic acid and phosphoribosyl formamidocarboxamide through its interaction with the enzyme bifunctional purine biosynthesis protein purh. In cattle, AICAR is involved in the metabolic pathway called the purine metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9613000000-e58f9c8b6a55e4f5a202View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0axr-6690400000-587ddf1606113df75d2dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0009000000-7425edce1492dba01a40View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1019000000-4ca07d05181423b32ed1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9300000000-5c28ca5957750fa338e3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-70e563a806a4c3a55e97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-74be45171db0b5560214View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-9104000000-230fd9fc88d41766b56eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0119000000-9504e432c77e845f195dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-1921000000-b59f42e588be20adfd16View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-2900000000-4725adb433c2ef4f7e01View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-731f94a980a3ea830720View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-5900000000-e2c302b537e2a87761caView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-2900000000-f0dad518d8c8a1fa40e2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-1960000000-d34b556d9bc2997b36ccView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00c3-1596000000-85bb5fa83829ab8f259eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-02i7-1591000000-165d1c4d5b3bb7d6208eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3910000000-75666864aadfb515185fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-3901000000-cf120ab9ca59f347fdd4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-249a325fdff8a321f364View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3910000000-9d01581a42f9d1ddbbafView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-84c17cba09b2fb11b4d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-ebd6a0aeccf60882a9c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-7900000000-674e1cf6f4488a373690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-9617000000-715abdd95d031de269f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-f3a4c70c454a0da6eb32View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3019a28f446b6ae4ee1fView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Skeletal Muscle
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Skeletal MuscleExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001517
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Adenine phosphoribosyltransferase
General function:
Nucleotide transport and metabolism
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:
Q56JW4
Molecular weight:
19537.0
Reactions
AICAR + Pyrophosphate → 5-Aminoimidazole-4-carboxamide + Phosphoribosyl pyrophosphatedetails
Enzyme Details
2. Bifunctional purine biosynthesis protein PURH
General function:
Nucleotide transport and metabolism
Specific function:
Bifunctional enzyme that catalyzes 2 steps in purine biosynthesis.
Gene Name:
ATIC
Uniprot ID:
Q0VCK0
Molecular weight:
64483.0
Reactions
N10-Formyl-THF + AICAR → Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamidedetails
Enzyme Details
3. Adenylosuccinate lyase
General function:
Nucleotide transport and metabolism
Specific function:
Catalyzes two non-sequential steps in de novo AMP synthesis: converts (S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate (SAICAR) to fumarate plus 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide, and thereby also contributes to de novo IMP synthesis, and converts succinyladenosine monophosphate (SAMP) to AMP and fumarate.
Gene Name:
ADSL
Uniprot ID:
A3KN12
Molecular weight:
55484.0
Reactions
SAICAR → Fumaric acid + AICARdetails