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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 is a very strong basic compound (based on its pKa).
Structure
Thumb
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
  • p(1),p(4)-Bis(5'-adenosyl) tetraphosphoric acid
  • Diadenosine tetraphosphate
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}({[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](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-10ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.6ChemAxon
pKa (Strongest Basic)5.29ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area433.97 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity166.1 m³·mol⁻¹ChemAxon
Polarizability67.57 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 + waterhydron + ADP
Adenosine triphosphate + hydron + ADPP1,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
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

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.
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.