Record Information
Version2.0
Creation Date2012-05-31 14:06:12 -0600
Update Date2015-09-17 15:41:18 -0600
Secondary Accession Numbers
  • ECMDB04138
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
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
Weight:Average: 720.2835
Monoisotopic: 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
DescriptionThis compound belongs to the class of chemical entities known as purine ribonucleoside triphosphates. These are purine ribobucleotides with a triphosphate group linked to the ribose moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassNucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Imidazole
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Azole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Alcohol
  • Organic oxide
  • Organonitrogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic 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:
SMPDB Pathways:
Quorum SensingPW000836 Pw000836Pw000836 greyscalePw000836 simple
Secondary Metabolites: Histidine biosynthesisPW000984 Pw000984Pw000984 greyscalePw000984 simple
histidine biosynthesisPW000810 Pw000810Pw000810 greyscalePw000810 simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
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

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
Uniprot ID:
P06989
Molecular weight:
22756
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.
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
Uniprot ID:
P60757
Molecular weight:
33366
Reactions
1-(5-phospho-D-ribosyl)-ATP + diphosphate = ATP + 5-phospho-alpha-D-ribose 1-diphosphate.

Transporters

General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane
Gene Name:
lsrC
Uniprot ID:
B1XEA2
Molecular weight:
36394
General function:
Involved in transporter activity
Specific function:
Part of the ABC transporter complex lsrABCD involved in autoinducer 2 (AI-2) import. Probably responsible for the translocation of the substrate across the membrane (Probable)
Gene Name:
lsrD
Uniprot ID:
P0AFS1
Molecular weight:
34456
General function:
ATPase activity, coupled to transmembrane movement of substances
Specific function:
Part of the ABC transporter complex LsrABCD involved in autoinducer 2 (AI-2) import. Responsible for energy coupling to the transport system (Probable). This protein is essential for aerobic growth.
Gene Name:
lsrA
Uniprot ID:
P77257
Molecular weight:
55820
General function:
periplasmic space
Specific function:
Part of the ABC transporter complex LsrABCD involved in autoinducer 2 (AI-2) import. Binds AI-2 and delivers it to the LsrC and LsrD permeases (Probable).
Gene Name:
lsrB
Uniprot ID:
P76142
Molecular weight:
36684