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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2007-05-22 20:52:31 UTC
Update Date2017-12-20 20:29:42 UTC
HMDB IDHMDB0006273
Secondary Accession Numbers
  • HMDB06273
Metabolite Identification
Common Name5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate
Description5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21].
Structure
Thumb
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
5-amino-1-(5-phospho-D-Ribosyl)imidazole-4-carboxylic acidGenerator
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
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-airMeSH
AICORMeSH
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 NumberNot Available
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
DescriptionThis compound 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-3.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.17ChemAxon
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
Polarizability28.52 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
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, Positivesplash10-0002-9613000000-2a087bcb710ee7b50b52View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00lu-2923230000-25e41df497cf1b5c9281View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-87d6bac417ced888900fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-e298883e772e11c253f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004i-8900000000-82583bffa17f1262d918View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-8928000000-d296c2812c7b06149794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-76793052d8d2699d70ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a8b367167e97f6df3690View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Adenine phosphoribosyltransferase deficiency (APRT)ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Adenosine Deaminase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Adenylosuccinate Lyase DeficiencyThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
AICA-RibosiduriaThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Azathioprine Action PathwayThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
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
FoodDB 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
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-carboxylate + L-Aspartic acid → ADP + Phosphoric acid + SAICARdetails
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-Aminoimidazole ribonucleotide + CO(2)details
5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate → 5-Aminoimidazole ribonucleotide + Carbon dioxidedetails
Adenosine triphosphate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate + L-Aspartic acid → ADP + Phosphoric acid + SAICARdetails