5-Amino-4-imidazolecarboxyamide (ECMDB20098) (M2MDB000946)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (365)
Record Information
Version2.0
Creation Date2012-05-31 14:27:23 -0600
Update Date2015-06-03 17:19:18 -0600
Secondary Accession Numbers
  • ECMDB20098
Identification
Name:5-Amino-4-imidazolecarboxyamide
Description5-Amino-4-imidazolecarboxyamide is a metabolite of purine metabolism. Adenine phosphoribosyltransferase [EC:2.4.2.7] catalyzes both the formation of 5-Amino-4-imidazolecarboxyamide and its conversion to 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide, also called AICAR. (KEGG)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1H-Imidazole-4-carboxamide, 5-amino-, monohydrochloride
  • 360-97-4 (FREE BASE)
  • 4-Amino-1H-imidazole-5-carboxamide
  • 4-Amino-5-carboxamido imidazole hydrochloride
  • 4-Amino-5-imidazole carboxamide
  • 4-Amino-5-Imidazolecarboxamide
  • 4-Amino-5-imidazolecarboxamide hydrochloride
  • 4-Aminoimidazole-5-carboxamide
  • 4-Aminoimidazole-5-carboxamide hydrochoride
  • 4-Carbamoyl-5-aminoimidazole
  • 4-Carboxamido-5-aminoimidazole
  • 5'-P-Ribosyl-5-amino-4-imidazole carboxamide
  • 5'-Phosphoribosyl-5-amino-4-imidazole carboxamide
  • 5(OR 4)-AMINO-IMIDAZOLE-4(OR 5)-CARBOXAMIDE
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
  • 5-Amino-1H-Imidazole-4-carboxamide
  • 5-Amino-4-imidazolecarboxamide
  • 5-Amino-4-imidazolecarboxamide ribotide
  • 5-Amino-Imidazole-4-carboxamide
  • 5-Aminoimidazol-4-carboxamide
  • 5-Aminoimidazol-4-carboxamide, hydrochloride
  • 5-Aminoimidazole carboxamide
  • 5-Aminoimidazole-4-carboxamide
  • 5-Aminoimidazole-4-carboxamide hydrochloride
  • 5-Aminoimidazole-4-carboxamide ribotide
  • 5-Aminoimidazolecarboxamide
  • 5-Imidazolecarboxamide, 4-amino-, hydrochloride
  • AIC
  • Aic .cntdot. HCL
  • AICA
  • AICA ribonucleotide
  • Aicar
  • Aminoimidazole carboxamide
  • Colahepat
  • Diazol-c
  • Imidazole C-4,5 deriv. 2
  • Imidazole-4-carboxamide, 5-amino-, monohydrochloride
  • WLN: T5M CNJ DVZ EZ
  • Z-Nucleotide
Chemical Formula:C4H6N4O
Weight:Average: 126.1166
Monoisotopic: 126.054160834
InChI Key:DVNYTAVYBRSTGK-UHFFFAOYSA-N
InChI:InChI=1S/C4H6N4O/c5-3-2(4(6)9)7-1-8-3/h1H,5H2,(H2,6,9)(H,7,8)
CAS number:72-40-2
IUPAC Name:4-amino-1H-imidazole-5-carboxamide
Traditional IUPAC Name:4-aminoimidazole-5-carboxamide
SMILES:NC(=O)C1=C(N)N=CN1
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoimidazoles. These are organic compounds containing an amino group linked to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassImidazoles
Direct ParentAminoimidazoles
Alternative Parents
Substituents
  • Aminoimidazole
  • Heteroaromatic compound
  • Azacycle
  • Carboximidic acid derivative
  • Carboximidic acid
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility124 g/LALOGPS
logP-1.2ALOGPS
logP-0.96ChemAxon
logS-0.01ALOGPS
pKa (Strongest Acidic)12.74ChemAxon
pKa (Strongest Basic)5.26ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area97.79 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity32.98 m³·mol⁻¹ChemAxon
Polarizability11.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
AICAR + Pyrophosphate <> 5-Amino-4-imidazolecarboxyamide + Phosphoribosyl pyrophosphate
Phosphoribulosylformimino-AICAR-P + L-Glutamine > L-Glutamic acid + Hydrogen ion + 5-Amino-4-imidazolecarboxyamide + D-Erythro-imidazole-glycerol-phosphate + L-Glutamate
SMPDB Pathways:
Secondary Metabolites: Histidine biosynthesisPW000984 ThumbThumb?image type=greyscaleThumb?image type=simple
histidine biosynthesisPW000810 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-0f9i-4965000000-81d31245e06d3f90edafView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0kgk-3936100000-5d3d51d18ff3e42df0e8View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0f9i-4965000000-81d31245e06d3f90edafView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0kgk-3936100000-5d3d51d18ff3e42df0e8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-3690000000-139a77fec9d1fff114cdView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f9i-1943000000-fc9ed76a2b879a05cac3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-0924100000-3f9bf805d01a76aee672View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-9700000000-59d0b74e7172f25684a9View 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 , negativesplash10-004i-0900000000-7f5a5c4e183bae4dac94View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-4900000000-f098009008beac308c09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4l-9100000000-0558a1cf6f49c407a5c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-49775423db52b263ab35View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-61b854e636df8aefa743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03fr-0900000000-dbf2f2a8c104b1886d61View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-4e7fa2397876cb8faa22View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-c5cc732d595521342e28View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9200000000-4f8ffe0195fc8b4eefb3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0a4i-9000000000-2475e395f0201d1ae8dcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0006-9000000000-e01c782c531e25d73332View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-5ac6303648d30c83dd8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03e9-5900000000-891e8af2ee696c82bb67View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9100000000-d969e00c4e0a26137fb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-5900000000-38872de2bfb260a5d96fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0563-9400000000-5d37f6e245dbc41ac3e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-9797d793034ec5f4f97fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-00d6654a49bf268f862dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-9300000000-8eb581fb8e27a0073ddeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-a1482203ba6eb659c755View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004l-8900000000-fa9ba502d467ade9fdcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-26ef6e91d6b3541e3748View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-74703663982d7ee978efView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID18406
HMDB IDHMDB0003192
Pubchem Compound ID9679
Kegg IDC04051
ChemSpider ID9298
Wikipedia IDNot Available
BioCyc IDAICAR
EcoCyc IDAICAR
Ligand Expo5AC

Enzymes

Protein Details
1. Adenine phosphoribosyltransferase
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:
apt
Uniprot ID:
P69503
Molecular weight:
19859
Reactions
AMP + diphosphate = adenine + 5-phospho-alpha-D-ribose 1-diphosphate.
Protein Details
2. Imidazole glycerol phosphate synthase subunit hisH
General function:
Involved in transferase activity, transferring pentosyl groups
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisH subunit provides the glutamine amidotransferase activity that produces the ammonia necessary to hisF for the synthesis of IGP and AICAR
Gene Name:
hisH
Uniprot ID:
P60595
Molecular weight:
21653
Reactions
5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-glutamine = imidazole-glycerol phosphate + 5-aminoimidazol-4-carboxamide ribonucleotide + L-glutamate + H(2)O.
Protein Details
3. Imidazole glycerol phosphate synthase subunit hisF
General function:
Involved in catalytic activity
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The hisF subunit catalyzes the cyclization activity that produces IGP and AICAR from PRFAR using the ammonia provided by the hisH subunit
Gene Name:
hisF
Uniprot ID:
P60664
Molecular weight:
28454
Reactions
5-[(5-phospho-1-deoxyribulos-1-ylamino)methylideneamino]-1-(5-phosphoribosyl)imidazole-4-carboxamide + L-glutamine = imidazole-glycerol phosphate + 5-aminoimidazol-4-carboxamide ribonucleotide + L-glutamate + H(2)O.