5',5'''-diadenosine tetraphosphate (PAMDB110550)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110550
Identification
Name: 5',5'''-diadenosine tetraphosphate
Description:Tetraanion of P1,P4-bis(5'-adenosyl) tetraphosphate arising from deprotonation of the tetraphosphate OH groups; major species at pH 7.3.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Ap4A
  • AppppA
  • P(1),P(4)-bis(5'-adenosyl)tetraphosphate
  • P1,P4-bis(5'-adenosyl)tetraphosphate
Chemical Formula: C20H24N10O19P4
Average Molecular Weight: 832.36
Monoisotopic Molecular Weight: 836.0482648107
InChI Key: YOAHKNVSNCMZGQ-XPWFQUROSA-J
InChI: InChI=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)/p-4/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
CAS number: 5542-28-9
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 Name: appppa
SMILES:C(C1(C(C(C(O1)N3(C=NC2(C(=NC=NC=23)N)))O)O))OP(OP(OP(OP(OCC4(C(C(C(O4)N6(C=NC5(C(=NC=NC=56)N)))O)O))([O-])=O)([O-])=O)([O-])=O)([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as (5'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub Class(5'->5')-dinucleotides
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
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Imidolactam
  • Pyrimidine
  • Heteroaromatic compound
  • Oxolane
  • Azole
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Primary amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-1.475Not Available
Predicted Properties
PropertyValueSource
Water Solubility5.59 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity166.1 m3·mol-1ChemAxon
Polarizability67.57 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910200030-f62591a77764336369caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-f3c88b3e116ab3d6c1b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-ed94ad304e91a867ff3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0019-0700020090-f52e6941bbc750fe0e76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900010000-dd233557a62d77a1406bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1915110000-741bdaae70092f502b8eView in MoNA
References
References:
  • 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. [17406124 ]
  • 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. [2141956 ]
  • Hoyle CH: Pharmacological activity of adenine dinucleotides in the periphery: possible receptor classes and transmitter function. Gen Pharmacol. 1990;21(6):827-31. [2279683 ]
  • 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. [9365907 ]
  • 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. [9826069 ]
  • 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. [9886880 ]
  • 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. [10082274 ]
  • Gualix J, Pintor J, Miras-Portugal MT: Characterization of nucleotide transport into rat brain synaptic vesicles. J Neurochem. 1999 Sep;73(3):1098-104. [10461900 ]
  • 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. [9113365 ]
  • 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. [510412 ]
  • 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. [11212966 ]
  • Jankowski J, Schluter H, Tepel M, Spieker C, Zidek W: Effect of diadenosine polyphosphates on Ca2+ ATPase activity. J Mol Med. 1997 Sep;75(9):674-7. [9351706 ]
  • 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. [9694344 ]
  • 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. [11810214 ]
  • 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. [12738682 ]
  • 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. [9607303 ]
  • 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. [8922753 ]
  • 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. [9187362 ]
  • 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. [16401072 ]
  • 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. [1953194 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI58141
HMDBHMDB01211
IAF12601484745
KEGGC01260
MetaboLightsMTBLC58141
PubChem25243905