Phosphoribosyl-ATP (PAMDB000631)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000631
Identification
Name: Phosphoribosyl-ATP
Description:Phosphoribosyl-ATP takes part in the Histidine Metabolism pathway.[KEGG ID C02739]. Specifically, Phosphoribosyl-ATP is substrate for phosphoribosyl pyrophosphate synthetase 1.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 1-(5-Phospho-D-ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphate)
  • 1-(5-phospho-D-Ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphoric acid)
  • 1-(5-Phospho-D-ribosyl)-ATP
  • 1-(5-Phosphoribosyl)-ATP
  • 5-Phosphoribosyl-ATP
  • N1-(5-Phospho-D-ribosyl)-ATP
  • PR-ATP
Chemical Formula: C15H26N5O20P4
Average Molecular Weight: 720.2835
Monoisotopic Molecular Weight: 720.012159345
InChI Key: KYTPWZMUSLPBJZ-UHFFFAOYSA-O
InChI:InChI=1S/C15H25N5O20P4/c16-12-7-13(18-4-19(12)14-10(23)8(21)5(37-14)1-35-41(25,26)27)20(3-17-7)15-11(24)9(22)6(38-15)2-36-43(31,32)40-44(33,34)39-42(28,29)30/h3-6,8-11,14-16,21-24H,1-2H2,(H6,25,26,27,28,29,30,31,32,33,34)/p+1
CAS number: Not Available
IUPAC Name:({[({[(2R,3S,4R,5R)-5-{1-[(3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-6-imino-6,9-dihydro-1H-purin-9-yl}-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid
Traditional IUPAC Name: Phosphoribosyl-ATP
SMILES:NC1=[N+](C=NC2=C1N=CN2C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O)C1OC(COP(O)(O)=O)C(O)C1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
Kingdom Organic compounds
Super ClassNucleosides, nucleotides, and analogues
Class Purine nucleotides
Sub ClassPurine ribonucleotides
Direct Parent Purine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Secondary alcohol
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-5
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-6.673PhysProp
Predicted Properties
PropertyValueSource
Water Solubility9.92 mg/mLALOGPS
logP-0.35ALOGPS
logP-5ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.66ChemAxon
pKa (Strongest Basic)1.71ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count20ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area383.23 Å2ChemAxon
Rotatable Bond Count12ChemAxon
Refractivity144.29 m3·mol-1ChemAxon
Polarizability56.94 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + Phosphoribosyl pyrophosphate <> Pyrophosphate + Phosphoribosyl-ATP
Water + Phosphoribosyl-ATP <> Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP
Phosphoribosyl-ATP + Water <> Phosphoribosyl-AMP + Pyrophosphate
Phosphoribosyl pyrophosphate + Hydrogen ion > Pyrophosphate + Phosphoribosyl-ATP + Phosphoribosyl-ATP
Phosphoribosyl-ATP + Water + Phosphoribosyl-ATP > Hydrogen ion + Pyrophosphate + Phosphoribosyl-AMP
(2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP + Water + (2R,4S)-2-Methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Phosphoribosyl-ATP > (2R,4S)-2-methyl-2,3,3,4-tetrahydroxytetrahydrofuran + Adenosine diphosphate + Hydrogen ion + Pyrophosphate + ADP
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0kaj-1739633400-e27af1b8e9489fa7241cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1926510000-b4ec6881b642250063e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001j-1943110000-bd22f77b44db9e4baba5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06dj-1647052900-24358b9ba8a747a31edeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9642210000-37824fa0d290e00eeb6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9420000000-314ee1336720e84cd8fcView in MoNA
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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID18263
HMDB IDHMDB03665
Pubchem Compound ID16019963
Kegg IDC02739
ChemSpider ID984
Wikipedia IDNot Available
BioCyc IDPHOSPHORIBOSYL-ATP
EcoCyc IDPHOSPHORIBOSYL-ATP

Enzymes

Protein Details
• Histidine biosynthesis bifunctional protein hisIE
General function:
Involved in phosphoribosyl-AMP cyclohydrolase activity
Specific function:
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5- phosphoribosyl)-AMP + diphosphate
Gene Name:
hisI
Locus Tag:
PA5066
Molecular weight:
15.4 kDa
Reactions
1-(5-phosphoribosyl)-ATP + H(2)O = 1-(5-phosphoribosyl)-AMP + diphosphate.
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
Protein Details
• ATP phosphoribosyltransferase
General function:
Involved in ATP phosphoribosyltransferase activity
Specific function:
Catalyzes the condensation of ATP and 5-phosphoribose 1- diphosphate to form N'-(5'-phosphoribosyl)-ATP (PR-ATP). Has a crucial role in the pathway because the rate of histidine biosynthesis seems to be controlled primarily by regulation of hisG enzymatic activity
Gene Name:
hisG
Locus Tag:
PA4449
Molecular weight:
22.8 kDa
Reactions
1-(5-phospho-D-ribosyl)-ATP + diphosphate = ATP + 5-phospho-alpha-D-ribose 1-diphosphate.

Transporters