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5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide (YMDB00562)

Identification
YMDB IDYMDB00562
Name5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
  • 1-(5-phosphoribosyl)-5-amino-4-imidazolecarboxamide
  • 1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxamide
  • 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
  • 5-Amino-4-imidazole carboxamide ribonucleotide
  • 5-amino-4-imidazolecarboxamide ribotide
  • 5-aminoimidazole-4-carboxamide ribotide
  • 5-phospho-ribosyl-5-amino-4-imidazole carboxamide
  • 5-phosphoribosyl-4-carbamoyl-5-aminoimidazole
  • 5-phosphoribosyl-5-amino-4-imidazolecarboxamide
  • 5'-P-ribosyl-5-amino-4-imidazole carboxamide
  • 5'-Phospho-ribosyl-5-amino-4-imidazole carboxamide
  • 5'-phosphoribosyl-5-amino-4-imidazole carboxamide
  • 5'-Phosphoribosyl-5-amino-4-imidazolecarboxamide
  • AICA ribonucleotide
  • aicar
  • aminoimidazole carboxamide ribonucleotide
  • Z-nucleotide
  • Acadesine 5'-monophosphate
  • AICA-Ribonucleotide
  • 5-Amino-1-(5-phospho-beta-D-ribosyl)imidazole-4-carboxamide
  • Acadesine 5'-monophosphoric acid
  • 5-Amino-1-(5-phospho-b-D-ribosyl)imidazole-4-carboxamide
  • 5-Amino-1-(5-phospho-β-D-ribosyl)imidazole-4-carboxamide
  • 4-Carboxy-5-aminoimidazole ribotide
  • 5-Amino-1-beta-D-ribofuranosylimidazole-4-carboxamide monophosphate
  • 5-Amino-4-imidazolecarboxamide ribofuranoside 5'-monophosphate
  • AICA Ribonucleotide, (D-ribofuranosyl)-isomer
  • AICAriboside 5'-monophosphate
  • CAIR
  • ZMP
  • (2R,3S,4R,5R)-5-(4-Carbam0yl-5-aminoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yljmethyl dihydrogen phosphate
  • 5'-Phospho-beta-D-ribosyl-5-amino-4-imidazolecarboxamide
  • 5'-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide
  • 5-Amino-1-(5'-phosphofuranoribosyl)-4-imidazolecarboxamide
  • 5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxamide
  • 5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxamide
  • 5-Amino-1-(5’-phosphofuranoribosyl)-4-imidazolecarboxamide
  • 5-Amino-1beta-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate
  • 5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5'-phosphate
  • 5-Amino-1β-D-ribofuranosylimidazole-4-carboxamide 5’-phosphate
  • 5-Amino-4-imidazolecarboxamide ribonucleoside 5'-monophosphate
  • 5-Amino-4-imidazolecarboxamide ribonucleoside 5’-monophosphate
  • 5-Amino-4-imidazolecarboxamide ribonucleotide
  • 5-Amino-4-imidazolecarboxamide riboside 5'-monophosphate
  • 5-Amino-4-imidazolecarboxamide riboside 5’-monophosphate
  • 5-Aminoimidazole-4-carboxamide ribonucleotide
  • 5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate
  • 5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate
  • 5’-Phospho-β-D-ribosyl-5-amino-4-imidazolecarboxamide
  • 5’-Phosphoribosyl-5-amino-4-imidazolecarboxamide
  • AICA Ribotide
  • AICAR (5-Aminoimidazole-4-carboxamide-1-beta-D-ribofuranosyl 5'-monophosphate)
  • AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5'-monophosphate)
  • AICAR (5-Aminoimidazole-4-carboxamide-1-β-D-ribofuranosyl 5’-monophosphate)
  • Acadesine 5’-monophosphate
  • Aminoimidazolecarboxamide ribonucleotide
CAS number3031-94-5
WeightAverage: 338.2112
Monoisotopic: 338.062749988
InChI KeyNOTGFIUVDGNKRI-UUOKFMHZSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,4R,5R)-5-(5-amino-4-carbamoyl-1H-imidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameaica ribonucleotide
Chemical FormulaC9H15N4O8P
SMILESNC(=O)C1=C(N)N(C=N1)[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.79 g/LALOGPS
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Histidine BiosynthesisPW002418 ThumbThumb?image type=greyscaleThumb?image type=simple
One Carbon Pool by Folate IPW002468 ThumbThumb?image type=greyscaleThumb?image type=simple
purine nucleotides de novo biosynthesisPW002478 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Histidine metabolismec00340 Map00340
Purine metabolismec00230 Map00230
SMPDB Reactions
Phosphoribulosylformimino-AICAR-P + L-Glutamine → L-Glutamic acid + hydron + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + D-Erythro-imidazole-glycerol-phosphate
Tetrahydrofolic acid + FAICAR → N10-Formyl-THF + 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
SAICAR → 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + Fumaric acid
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + N10-Formyl-THF → FAICAR + tetrahydropteroyl mono-L-glutamate
KEGG Reactions
SAICAR ↔ 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + Fumaric acid
5-[(5-phospho-1-deoxy-D-ribulos-1-ylimino)methylamino]-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + L-Glutamine → 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + L-Glutamic acid + hydron + D-Erythro-imidazole-glycerol-phosphate
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide + N10-Formyl-THF ↔ 5,6,7,8-Tetrahydrofolic acid + Phosphoribosyl formamidocarboxamide
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9613000000-e58f9c8b6a55e4f5a202JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0axr-6690400000-587ddf1606113df75d2dJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0009000000-7425edce1492dba01a40JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-1019000000-4ca07d05181423b32ed1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004j-9300000000-5c28ca5957750fa338e3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9200000000-70e563a806a4c3a55e97JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9100000000-74be45171db0b5560214JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004r-9104000000-230fd9fc88d41766b56eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-000i-0119000000-9504e432c77e845f195dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-056r-1921000000-b59f42e588be20adfd16JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-2900000000-4725adb433c2ef4f7e01JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-731f94a980a3ea830720JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-5900000000-e2c302b537e2a87761caJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-2900000000-f0dad518d8c8a1fa40e2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-03di-1960000000-d34b556d9bc2997b36ccJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00c3-1596000000-85bb5fa83829ab8f259eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-02i7-1591000000-165d1c4d5b3bb7d6208eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3910000000-75666864aadfb515185fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-3901000000-cf120ab9ca59f347fdd4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03di-4900000000-249a325fdff8a321f364JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-004i-3910000000-9d01581a42f9d1ddbbafJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0914000000-84c17cba09b2fb11b4d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01t9-1900000000-ebd6a0aeccf60882a9c4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-7900000000-674e1cf6f4488a373690JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004r-9617000000-715abdd95d031de269f0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9400000000-f3a4c70c454a0da6eb32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-3019a28f446b6ae4ee1fJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Pinson, B., Vaur, S., Sagot, I., Coulpier, F., Lemoine, S., Daignan-Fornier, B. (2009). "Metabolic intermediates selectively stimulate transcription factor interaction and modulate phosphate and purine pathways." Genes Dev 23:1399-1407.19528318
Synthesis Reference:Schmitt, 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 & N
External Links:
ResourceLink
CHEBI ID18406
HMDB IDHMDB01517
Pubchem Compound ID65110
Kegg IDC04677
ChemSpider ID58620
FOODB IDFDB030675
WikipediaAICA ribonucleotide
BioCyc IDAICAR

Enzymes

Protein Details
1. Imidazole glycerol phosphate synthase hisHF
General function:
Involved in catalytic activity
Specific function:
IGPS catalyzes the conversion of PRFAR and glutamine to IGP, AICAR and glutamate. The glutamine amidotransferase domain provides the ammonia necessary to the cyclase domain to produce IGP and AICAR from PRFAR
Gene Name:
HIS7
Uniprot ID:
P33734
Molecular weight:
61067.60156
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
2. Adenylosuccinate lyase
General function:
Involved in catalytic activity
Specific function:
N(6)-(1,2-dicarboxyethyl)AMP = fumarate + AMP
Gene Name:
ADE13
Uniprot ID:
Q05911
Molecular weight:
54509.89844
Reactions
N(6)-(1,2-dicarboxyethyl)AMP → fumarate + AMP.
(S)-2-(5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamido)succinate → fumarate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
Protein Details
3. Bifunctional purine biosynthesis protein ADE17
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE17
Uniprot ID:
P38009
Molecular weight:
65262.60156
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
Protein Details
4. Bifunctional purine biosynthesis protein ADE16
General function:
Involved in IMP cyclohydrolase activity
Specific function:
10-formyltetrahydrofolate + 5-amino-1-(5- phospho-D-ribosyl)imidazole-4-carboxamide = tetrahydrofolate + 5- formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide
Gene Name:
ADE16
Uniprot ID:
P54113
Molecular weight:
65281.80078
Reactions
10-formyltetrahydrofolate + 5-amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide → tetrahydrofolate + 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.
IMP + H(2)O → 5-formamido-1-(5-phospho-D-ribosyl)imidazole-4-carboxamide.