P1,P4-Bis(5'-adenosyl) tetraphosphate (YMDB00225)

Identification
YMDB IDYMDB00225
NameP1,P4-Bis(5'-adenosyl) tetraphosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionDiadenosine tetraphosphate, also known as appppa or (ppa)2, belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. Diadenosine tetraphosphate exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Diadenosine tetraphosphate.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • A(5')p4(5')A
  • adenosine(5')tetraphospho(5')adenosine
  • bis(5'-adenylyl) diphosphate
  • P(1),P(4)-bis(5'-adenosyl) tetraphosphate
  • (PpA)2
  • AppppA
  • P1,P4-Bis(5'-adenosyl) tetraphosphate
  • Bis(5'-adenylyl) diphosphoric acid
  • P1,P4-Bis(5'-adenosyl) tetraphosphoric acid
  • Diadenosine tetraphosphoric acid
  • 5',5'''-diadenosine tetraphosphate
  • Adenosine 5'-tetraphosphate, 5'-ester with adenosine
  • Adenosine-(5')-tetraphospho-(5')-adenosine
  • Diadenosine 5',5'''-P1,P4-tetraphosphate
  • P1,P4-Di(adenosin-5'-yl)tetraphosphate
  • P1,P4-Diadenosine-5'-tetraphosphate
  • Ap4a
  • P(1), P(4)-Diadenosine-5'tetraphosphate
  • Diadenosine 5',5'''-P(1),P(4)--tetraphosphate
  • Bis(5'-adenosyl)tetraphosphate
  • P1,P4-Bis(5'-adenosyl)tetraphosphoric acid
  • Diadenosine tetraphosphate
  • p(1),p(4)-Bis(5'-adenosyl) tetraphosphoric acid
CAS numberNot Available
WeightAverage: 836.387
Monoisotopic: 836.048264812
InChI KeyYOAHKNVSNCMZGQ-XPWFQUROSA-N
InChIInChI=1S/C20H28N10O19P4/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid
Traditional IUPAC Nameappppa
Chemical FormulaC20H28N10O19P4
SMILESNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)N4C=NC5=C(N)N=CN=C45)[C@@H](O)[C@H]3O)C2=NC=N1
Chemical Taxonomy
Description belongs to the class of organic compounds known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(5'->5')-dinucleotides
Sub ClassNot Available
Direct Parent(5'->5')-dinucleotides
Alternative Parents
Substituents
  • (5'->5')-dinucleotide
  • Purine ribonucleoside polyphosphate
  • Purine nucleotide sugar
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Phosphoric acid ester
  • Imidolactam
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary alcohol
  • Azacycle
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Amine
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility5.59 g/LALOGPS
logP-0.71ALOGPS
logP-9.5ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.59ChemAxon
pKa (Strongest Basic)4.28ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area433.97 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity166.1 m³·mol⁻¹ChemAxon
Polarizability66.83 ųChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Purine metabolismec00230 Map00230
SMPDB ReactionsNot Available
KEGG Reactions
P1,P4-Bis(5'-adenosyl) tetraphosphate + water ↔ hydron + ADP
Adenosine triphosphate + hydron + ADP → P1,P4-Bis(5'-adenosyl) tetraphosphate + phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910200030-f62591a77764336369caJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f3c88b3e116ab3d6c1b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-ed94ad304e91a867ff3bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0700020090-f52e6941bbc750fe0e76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900010000-dd233557a62d77a1406bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1915110000-741bdaae70092f502b8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0100000090-0703d63dcb1429245411JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0300002090-89e8cc71cfb144d0f8b6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900101000-4b74d668fd588964dfd6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-bc4ce7d28b2ff5fc83e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0201132090-cd2f5d95fa2a2c4f170aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0410920120-5c5c92a5ab82e5e045d2JSpectraViewer
MSMass Spectrum (Electron Ionization)Not 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
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 ID17422
HMDB IDHMDB06502
Pubchem Compound ID194
Kegg IDC01260
ChemSpider ID20402
FOODB IDFDB022492
Wikipedia IDAp4A
BioCyc IDNot Available

Enzymes

Protein Details
1. Protein APA1
General function:
Involved in ATP adenylyltransferase activity
Specific function:
Ap4A phosphorylase catabolizes Ap4N nucleotides (where N is A,C,G or U). Additionally this enzyme catalyzes the conversion of adenosine-5-phosphosulfate (AMPs) plus Pi to ADP plus sulfate, the exchange of NDP and phosphate and the synthesis of Ap4A from AMPs plus ATP
Gene Name:
APA1
Uniprot ID:
P16550
Molecular weight:
36492.19922
Reactions
ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.
ADP + sulfate → phosphate + adenylyl sulfate.
Adenylylsulfate + ATP → P(1),P(4)-bis(5'-adenosyl)tetraphosphate + sulfate.
Protein Details
2. 5',5'''-P-1,P-4-tetraphosphate phosphorylase 2
General function:
Involved in ATP adenylyltransferase activity
Specific function:
Sustains the catabolism of Np-4-N' nucleotides, rather than their synthesis
Gene Name:
APA2
Uniprot ID:
P22108
Molecular weight:
36840.5
Reactions
ADP + ATP → phosphate + P(1),P(4)-bis(5'-adenosyl) tetraphosphate.