Record Information
Version1.0
Created at2020-04-17 19:11:19 UTC
Updated at2020-11-18 16:39:24 UTC
CannabisDB IDCDB005120
Secondary Accession NumbersNot Available
Cannabis Compound 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. AICAR is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
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 Weight338.21
Monoisotopic Molecular Weight338.0627
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:

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
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSAICAR, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9613000000-e58f9c8b6a55e4f5a202Spectrum
Predicted GC-MSAICAR, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0axr-6690400000-587ddf1606113df75d2dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0009000000-7425edce1492dba01a40Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1019000000-4ca07d05181423b32ed1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9300000000-5c28ca5957750fa338e3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-70e563a806a4c3a55e97Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-74be45171db0b5560214Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-9104000000-230fd9fc88d41766b56eSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0119000000-9504e432c77e845f195dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-1921000000-b59f42e588be20adfd16Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-2900000000-4725adb433c2ef4f7e01Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-731f94a980a3ea830720Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-5900000000-e2c302b537e2a87761caSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-2900000000-f0dad518d8c8a1fa40e2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-84c17cba09b2fb11b4d1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-ebd6a0aeccf60882a9c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-7900000000-674e1cf6f4488a373690Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-9617000000-715abdd95d031de269f0Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-f3a4c70c454a0da6eb32Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3019a28f446b6ae4ee1fSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Adenine phosphoribosyltransferaseAPRT16q24P07741 details
Adenylosuccinate lyaseADSL22q13.2P30566 details
Bifunctional purine biosynthesis protein PURHATIC2q35P31939 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0001517
DrugBank IDDB01700
Phenol Explorer Compound IDNot Available
FoodDB 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
General ReferencesNot Available

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
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
ADSL
Uniprot ID:
P30566
Molecular weight:
54888.735
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