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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 20:52:31 UTC
Update Date2020-03-06 18:54:40 UTC
HMDB IDHMDB0006273
Secondary Accession Numbers
  • HMDB06273
Metabolite Identification
Common Name5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
Description5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid, also known as 1-(5'-phosphoribosyl)-4-carboxy-5-aminoimidazole or 1-(5-phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid, belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is a very strong basic compound (based on its pKa). 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid exists in all living species, ranging from bacteria to humans. Within humans, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid participates in a number of enzymatic reactions. In particular, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid can be converted into 5-aminoimidazole ribonucleotide; which is mediated by the enzyme multifunctional protein ADE2. In addition, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid and L-aspartic acid can be converted into SAICAR; which is mediated by the enzyme multifunctional protein ADE2. In humans, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is involved in the metabolic disorder called Lesch-Nyhan syndrome (LNS). Outside of the human body, 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid has been detected, but not quantified in, several different foods, such as ohelo berries, Chinese mustards, peach (var.), jackfruits, and saskatoon berries. This could make 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid a potential biomarker for the consumption of these foods. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is an intermediate in purine metabolism. 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase (EC: 4.1.1.21).
Structure
Data?1583520879
Synonyms
ValueSource
1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazoleChEBI
1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazoleChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylateChEBI
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylateChEBI
5'-Phosphoribosyl-4-carboxy-5-aminoimidazoleChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylateChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acidGenerator
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acidGenerator
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acidGenerator
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acidGenerator
4-Carboxy-5-aminoimidazole ribonucleotideHMDB
5'Phosphoribosyl-4-carboxy-5-aminoimidazoleHMDB
5-Amino-4-carboxyimidazole ribonucleotideHMDB
5-Amino-4-imidazolecarboxylic acid ribonucleotideHMDB
5-Aminoimidazole carboxilic acid ribonucleoticeHMDB
5-Aminoimidazole-4-carboxilic acid ribonucleotideHMDB
Carboxyaminoimidazole ribonucleotideHMDB
Carboxy-airHMDB
AICORHMDB
Carboxyaminoimidazole ribotideMeSH
CAIRMeSH
5-Amino-1-(5-O-phosphonopentofuranosyl)-1H-imidazole-4-carboxylic acidMeSH
1-(5’-Phosphoribosyl)-4-carboxy-5-aminoimidazoleHMDB
1-(5’-Phosphoribosyl)-5-amino-4-carboxyimidazoleHMDB
1-(5’-Phosphoribosyl)-5-amino-4-imidazolecarboxylateHMDB
5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acidHMDB
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acidHMDB
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylateHMDB
5-Aminoimidazole 4-carboxylic acid ribonucleotideHMDB
5-Aminoimidazolecarboxylic acid ribonucleotideHMDB
5’-Phosphoribosyl-4-carboxy-5-aminoimidazoleHMDB
5’-Phosphoribosyl-5-amino-4-imidazolecarboxylateHMDB
Chemical FormulaC9H14N3O9P
Average Molecular Weight339.1959
Monoisotopic Molecular Weight339.046765573
IUPAC Name5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid
Traditional Name5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid
CAS Registry Number6001-14-5
SMILES
NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1
InChI KeyXFVULMDJZXYMSG-ZIYNGMLESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPentose phosphates
Alternative Parents
Substituents
  • Pentose phosphate
  • Pentose-5-phosphate
  • Imidazole ribonucleoside
  • N-glycosyl compound
  • Glycosyl compound
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Imidazole-4-carbonyl group
  • Alkyl phosphate
  • Phosphoric acid ester
  • Aminoimidazole
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Azole
  • Vinylogous amide
  • Tetrahydrofuran
  • Imidazole
  • Heteroaromatic compound
  • 1,2-diol
  • Secondary alcohol
  • Amino acid
  • Amino acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Amine
  • Organopnictogen compound
  • Organic oxide
  • Primary amine
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility2.81 g/LALOGPS
logP-2ALOGPS
logP-3.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.18ChemAxon
pKa (Strongest Basic)7.11ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area197.59 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity67.32 m³·mol⁻¹ChemAxon
Polarizability28.49 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-0002-9613000000-2a087bcb710ee7b50b52Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00lu-2923230000-25e41df497cf1b5c9281Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-87d6bac417ced888900fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-e298883e772e11c253f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8900000000-82583bffa17f1262d918Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-8928000000-d296c2812c7b06149794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-76793052d8d2699d70ddSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a8b367167e97f6df3690Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023871
KNApSAcK IDNot Available
Chemspider ID144983
KEGG Compound IDC04751
BioCyc IDPHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE
BiGG ID44477
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound165388
PDB IDC2R
ChEBI ID28413
Food Biomarker OntologyNot Available
VMH ID5AIZC
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in phosphoribosylaminoimidazole carboxylase activity
Specific function:
Not Available
Gene Name:
PAICS
Uniprot ID:
P22234
Molecular weight:
47078.82
Reactions
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid + L-Aspartic acid → ADP + Phosphate + SAICARdetails
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + CO(2)details
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid → 5-Aminoimidazole ribonucleotide + Carbon dioxidedetails
Adenosine triphosphate + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid + L-Aspartic acid → ADP + Phosphate + SAICARdetails