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Identification
YMDB IDYMDB00165
NamePhosphoribosyl-ATP
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphoribosyl-ATP 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. Phosphoribosyl-ATP is an extremely weak basic (essentially neutral) compound (based on its pKa). Phosphoribosyl-ATP exists in all eukaryotes, ranging from yeast to humans.
Structure
Thumb
Synonyms
  • 1-(5-phospho-D-ribofuranosyl)adenosine 5'-(tetrahydrogen triphosphate)
  • 1-(5-phospho-D-ribosyl)-ATP
  • 1-(5-Phosphoribosyl)-ATP
  • N1-(5-Phospho-D-ribosyl)-ATP
CAS numberNot Available
WeightAverage: 720.2835
Monoisotopic: 720.012159345
InChI KeyKYTPWZMUSLPBJZ-UHFFFAOYSA-O
InChIInChI=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
IUPAC Name6-amino-9-[3,4-dihydroxy-5-({[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}methyl)oxolan-2-yl]-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-9H-1λ⁵-purin-1-ylium
Traditional IUPAC Name6-amino-1-{3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl}-9-{3,4-dihydroxy-5-[({hydroxy[hydroxy(phosphonooxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-2-yl}-1λ⁵-purin-1-ylium
Chemical FormulaC15H26N5O20P4
SMILES[H]OC1([H])C([H])(OC([H])(C([H])([H])OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O[H])C1([H])O[H])N1C([H])=NC2=C1N=C([H])[N+](=C2N([H])[H])C1([H])OC([H])(C([H])([H])OP(=O)(O[H])O[H])C([H])(O[H])C1([H])O[H]
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside triphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside triphosphate
  • Purine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Monosaccharide
  • N-substituted imidazole
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Organic phosphoric acid derivative
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Tetrahydrofuran
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Organic nitrogen compound
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP-6.673PhysProp
Predicted Properties
PropertyValueSource
Water Solubility4.75 g/LALOGPS
logP-0.04ALOGPS
logP-11ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.03ChemAxon
pKa (Strongest Basic)0.54ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area386.57 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity132.86 m³·mol⁻¹ChemAxon
Polarizability57.46 ųChemAxon
Number of Rings4ChemAxon
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
KEGG Pathways
Histidine metabolismec00340 Map00340
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18263
HMDB IDHMDB03665
Pubchem Compound ID16019963
Kegg IDC02739
ChemSpider ID24808125
FOODB IDFDB023212
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

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 the enzymatic activity
Gene Name:
HIS1
Uniprot ID:
P00498
Molecular weight:
32266.09961
Reactions
1-(5-phospho-D-ribosyl)-ATP + diphosphate → ATP + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in oxidoreductase activity
Specific function:
1-(5-phosphoribosyl)-AMP + H(2)O = 1-(5- phosphoribosyl)-5-((5- phosphoribosylamino)methylideneamino)imidazole-4-carboxamide
Gene Name:
HIS4
Uniprot ID:
P00815
Molecular weight:
87720.5
Reactions
1-(5-phosphoribosyl)-AMP + H(2)O → 1-(5-phosphoribosyl)-5-((5-phosphoribosylamino)methylideneamino)imidazole-4-carboxamide.
1-(5-phosphoribosyl)-ATP + H(2)O → 1-(5-phosphoribosyl)-AMP + diphosphate.
L-histidinol + H(2)O + 2 NAD(+) → L-histidine + 2 NADH.