Diadenosine tetraphosphate (CHEM035122)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:30:26 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035122
Identification
Common NameDiadenosine tetraphosphate
ClassSmall Molecule
DescriptionA diadenosyl tetraphosphate compound having the two 5'-adenosyl residues attached at the P(1)- and P(4)-positions.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(PpA)2ChEBI
a(5')P4(5')aChEBI
AppppAChEBI
Bis(5'-adenylyl) diphosphateChEBI
P1,P4-Bis(5'-adenosyl) tetraphosphateChEBI
Bis(5'-adenylyl) diphosphoric acidGenerator
P1,P4-Bis(5'-adenosyl) tetraphosphoric acidGenerator
Diadenosine tetraphosphoric acidGenerator
5',5'''-diadenosine tetraphosphateHMDB
Adenosine 5'-tetraphosphate, 5'-ester with adenosineHMDB
Adenosine-(5')-tetraphospho-(5')-adenosineHMDB
Diadenosine 5',5'''-P1,P4-tetraphosphateHMDB
P1,P4-Di(adenosin-5'-yl)tetraphosphateHMDB
P1,P4-Diadenosine-5'-tetraphosphateHMDB
Ap4aMeSH, HMDB
P(1), P(4)-Diadenosine-5'tetraphosphateMeSH, HMDB
Diadenosine 5',5'''-P(1),P(4)--tetraphosphateMeSH, HMDB
Adenosine(5')tetraphospho(5')adenosineMeSH, HMDB
Bis(5'-adenosyl)tetraphosphateMeSH, HMDB
P1,P4-Bis(5'-adenosyl)tetraphosphoric acidGenerator, HMDB
Diadenosine tetraphosphateMeSH
p(1),p(4)-Bis(5'-adenosyl) tetraphosphoric acidGenerator, HMDB
Chemical FormulaC20H28N10O19P4
Average Molecular Mass836.387 g/mol
Monoisotopic Mass836.048 g/mol
CAS Registry Number5542-28-9
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 Nameappppa
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
InChI IdentifierInChI=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
InChI KeyYOAHKNVSNCMZGQ-XPWFQUROSA-N
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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910200030-f62591a77764336369caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f3c88b3e116ab3d6c1b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-ed94ad304e91a867ff3bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0700020090-f52e6941bbc750fe0e76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900010000-dd233557a62d77a1406bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1915110000-741bdaae70092f502b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0100000090-0703d63dcb1429245411Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0300002090-89e8cc71cfb144d0f8b6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900101000-4b74d668fd588964dfd6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000000090-bc4ce7d28b2ff5fc83e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0201132090-cd2f5d95fa2a2c4f170aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4r-0410920120-5c5c92a5ab82e5e045d2Spectrum
MSMass Spectrum (Electron Ionization)Not AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001211
FooDB IDFDB022492
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAp4A
Chemspider ID20402
ChEBI ID17422
PubChem Compound ID21706
Kegg Compound IDC01260
YMDB IDYMDB00225
ECMDB IDECMDB01211
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Stiepanow-Trzeciak A, Jankowski M, Angielski S, Szczepanska-Konkel M: P1,P4-diadenosine tetraphosphate (Ap4A) inhibits proximal tubular reabsorption of sodium in rats. Nephron Physiol. 2007;106(1):p13-8. Epub 2007 Apr 2.
2. de Korte D, Gouwerok CW, Fijnheer R, Pietersz RN, Roos D: Depletion of dense granule nucleotides during storage of human platelets. Thromb Haemost. 1990 Apr 12;63(2):275-8.
3. Hoyle CH: Pharmacological activity of adenine dinucleotides in the periphery: possible receptor classes and transmitter function. Gen Pharmacol. 1990;21(6):827-31.
4. Pintor J, Puche JA, Gualix J, Hoyle CH, Miras-Portugal MT: Diadenosine polyphosphates evoke Ca2+ transients in guinea-pig brain via receptors distinct from those for ATP. J Physiol. 1997 Oct 15;504 ( Pt 2):327-35.
5. Hourani SM, Bailey SJ, Johnson CR, Tennant JP: Effects of adenosine 5'-triphosphate, uridine 5'-triphosphate, adenosine 5'-tetraphosphate and diadenosine polyphosphates in guinea-pig taenia caeci and rat colon muscularis mucosae. Naunyn Schmiedebergs Arch Pharmacol. 1998 Oct;358(4):464-73.
6. van der Giet M, Jankowski J, Schluter H, Zidek W, Tepel M: Mediation of the vasoactive properties of diadenosine tetraphosphate via various purinoceptors. J Hypertens. 1998 Dec;16(12 Pt 2):1939-43.
7. Wildman SS, Brown SG, King BF, Burnstock G: Selectivity of diadenosine polyphosphates for rat P2X receptor subunits. Eur J Pharmacol. 1999 Feb 12;367(1):119-23.
8. Gualix J, Pintor J, Miras-Portugal MT: Characterization of nucleotide transport into rat brain synaptic vesicles. J Neurochem. 1999 Sep;73(3):1098-104.
9. van der Giet M, Khattab M, Borgel J, Schluter H, Zidek W: Differential effects of diadenosine phosphates on purinoceptors in the rat isolated perfused kidney. Br J Pharmacol. 1997 Apr;120(8):1453-60.
10. Pirrone AM, Gambino R, Oddo F, Faraci MT, Luparello G, Giudice G: Sea urchin embryos do not synthesize diadenosinetetraphosphate. Exp Cell Res. 1979 Sep;122(2):419-22.
11. Hollah P, Hausberg M, Kosch M, Barenbrock M, Letzel M, Schlatter E, Rahn KH: A novel assay for determination of diadenosine polyphosphates in human platelets: studies in normotensive subjects and in patients with essential hypertension. J Hypertens. 2001 Feb;19(2):237-45.
12. Jankowski J, Jankowski V, Laufer U, van der Giet M, Henning L, Tepel M, Zidek W, Schluter H: Identification and quantification of diadenosine polyphosphate concentrations in human plasma. Arterioscler Thromb Vasc Biol. 2003 Jul 1;23(7):1231-8. Epub 2003 May 8.
13. Pintor J, Carracedo G, Alonso MC, Bautista A, Peral A: Presence of diadenosine polyphosphates in human tears. Pflugers Arch. 2002 Jan;443(3):432-6. Epub 2001 Aug 23.
14. Kisselev LL, Justesen J, Wolfson AD, Frolova LY: Diadenosine oligophosphates (Ap(n)A), a novel class of signalling molecules? FEBS Lett. 1998 May 8;427(2):157-63.
15. Pintor J, King BF, Miras-Portugal MT, Burnstock G: Selectivity and activity of adenine dinucleotides at recombinant P2X2 and P2Y1 purinoceptors. Br J Pharmacol. 1996 Nov;119(5):1006-12.
16. Turpaev K, Hartmann R, Kisselev L, Justesen J: Ap3A and Ap4A are primers for oligoadenylate synthesis catalyzed by interferon-inducible 2-5A synthetase. FEBS Lett. 1997 May 19;408(2):177-81.
17. Baker MD, Holloway DE, Swaminathan GJ, Acharya KR: Crystal structures of eosinophil-derived neurotoxin (EDN) in complex with the inhibitors 5'-ATP, Ap3A, Ap4A, and Ap5A. Biochemistry. 2006 Jan 17;45(2):416-26.
18. Stachon A, Stegemann H, Hohage H, Rahn KH, Schlatter E: Effects of diadenosine polyphosphates on the intracellular Ca2+ concentration in endothelial cells. Cell Physiol Biochem. 1998;8(4):175-84.
19. Jankowski J, Schluter H, Tepel M, Spieker C, Zidek W: Effect of diadenosine polyphosphates on Ca2+ ATPase activity. J Mol Med (Berl). 1997 Sep;75(9):674-7.
20. Chan PJ, Su BC, Tredway DR: Diadenosine tetraphosphate (Ap4A) and triphosphate (Ap3A) signaling of human sperm motility. Arch Androl. 1991 Sep-Oct;27(2):103-8.