Diadenosine hexaphosphate (CHEM035152)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:31:55 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035152
Identification
Common NameDiadenosine hexaphosphate
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Adenosine 5'-hexaphosphate 5'-ester with adenosineChEBI
Adenosine-(5')-hexaphospho-(5')-adenosineChEBI
Ap(6)aChEBI
AP6aChEBI
AppppppAChEBI
Diadenosine 5',5''''-P1,P6-hexaphosphateChEBI
P1,P6-Di(adenosine-5')hexaphosphateChEBI
Adenosine 5'-hexaphosphoric acid 5'-ester with adenosineGenerator
Diadenosine 5',5''''-P1,P6-hexaphosphoric acidGenerator
P1,P6-Di(adenosine-5')hexaphosphoric acidGenerator
Diadenosine hexaphosphoric acidGenerator
Adenosine 5'-(heptahydrogen hexaphosphate) p->5'-ester with adenosineHMDB
Adenosine 5'-(heptahydrogen hexaphosphate)5'-5'-ester with adenosineHMDB
P1,P6-Bis(5'-adenosyl)hexaphosphoric acidHMDB
p(1),p(6)-Bis(5'-adenosyl)hexaphosphoric acidHMDB
Diadenosine hexaphosphateChEBI
Chemical FormulaC20H30N10O25P6
Average Molecular Mass996.347 g/mol
Monoisotopic Mass995.981 g/mol
CAS Registry Number56983-23-4
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}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphinic acid
Traditional NameAppppppA
SMILESNC1=C2N=CN([C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(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/C20H30N10O25P6/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(49-19)1-47-56(35,36)51-58(39,40)53-60(43,44)55-61(45,46)54-59(41,42)52-57(37,38)48-2-8-12(32)14(34)20(50-8)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)(H,43,44)(H,45,46)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
InChI KeyPZCFFCOJNXGTIM-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 Solubility6.99 g/LALOGPS
logP0.26ALOGPS
logP-10ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.28ChemAxon
pKa (Strongest Basic)5.3ChemAxon
Physiological Charge-6ChemAxon
Hydrogen Acceptor Count26ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area527.03 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity187.85 m³·mol⁻¹ChemAxon
Polarizability76.38 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-0910110002-59d115c90a4481a6b007Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0900000000-d3bcef479d59e691d5b8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000000-8dec47b8f02e8a6ac5a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-0700000209-de23da8b809775f36d57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000200-eec87d1063e1b19d703aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-1902401000-c06f9d4097503496c4b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000000009-1da203db6bf6303096a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0100001329-9afe5ff0f93ff13bf2a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000b-0103149204-ccb4974c1451a6de78f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0100000009-e59c713225edd8e0460dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0300000039-0a05007bbbf9147ab5f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0900000110-66251e85696bf2211dd4Spectrum
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 IDHMDB0001282
FooDB IDFDB022533
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDB6P
Wikipedia LinkNot Available
Chemspider ID110267
ChEBI ID63689
PubChem Compound ID123694
Kegg Compound IDC20190
YMDB IDNot Available
ECMDB IDECMDB24064
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sawai, Hiroaki; Inaba, Toshiko; Hirano, Atsushi; Wakai, Hiromichi; Shimazu, Masamitsu. Magnesium(II) ion-mediated conversion of mono- and oligonucleotides to 5'-polyphosphates in aqueous solution. Tetrahedron Letters (1993), 34(30), 4801-4.
2. Jankowski J, Potthoff W, van der Giet M, Tepel M, Zidek W, Schluter H: High-performance liquid chromatographic assay of the diadenosine polyphosphates in human platelets. Anal Biochem. 1999 Apr 10;269(1):72-8.
3. Flores NA, Stavrou BM, Sheridan DJ: The effects of diadenosine polyphosphates on the cardiovascular system. Cardiovasc Res. 1999 Apr;42(1):15-26.
4. Jankowski J, Tepel M, van der Giet M, Tente IM, Henning L, Junker R, Zidek W, Schluter H: Identification and characterization of P(1), P(7)-Di(adenosine-5')-heptaphosphate from human platelets. J Biol Chem. 1999 Aug 20;274(34):23926-31.
5. Luo J, Jankowski J, Tepel M, von Der Giet M, Zidek W, Schluter H: Identification of diadenosine hexaphosphate in human erythrocytes. Hypertension. 1999 Oct;34(4 Pt 2):872-5.
6. Yang X, Safrany ST, Shears SB: Site-directed mutagenesis of diphosphoinositol polyphosphate phosphohydrolase, a dual specificity NUDT enzyme that attacks diadenosine polyphosphates and diphosphoinositol polyphosphates. J Biol Chem. 1999 Dec 10;274(50):35434-40.
7. Conant AR, Fisher MJ, McLennan AG, Simpson AW: Diadenosine polyphosphates are largely ineffective as agonists at natively expressed P2Y(1) and P2Y(2) receptors on cultured human saphenous vein endothelial cells. J Vasc Res. 2000 Nov-Dec;37(6):548-55.
8. 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.
9. Patel K, Barnes A, Camacho J, Paterson C, Boughtflower R, Cousens D, Marshall F: Activity of diadenosine polyphosphates at P2Y receptors stably expressed in 1321N1 cells. Eur J Pharmacol. 2001 Nov 2;430(2-3):203-10.
10. Steinmetz M, Janssen AK, Pelster F, Rahn KH, Schlatter E: Vasoactivity of diadenosine polyphosphates in human small mesenteric resistance arteries. J Pharmacol Exp Ther. 2002 Aug;302(2):787-94.
11. Miras-Portugal MT, Pintor J, Gualix J: Ca2+ signalling in brain synaptosomes activated by dinucleotides. J Membr Biol. 2003 Jul 1;194(1):1-10.
12. Luo J, Jankowski V, Gungar N, Neumann J, Schmitz W, Zidek W, Schluter H, Jankowski J: Endogenous diadenosine tetraphosphate, diadenosine pentaphosphate, and diadenosine hexaphosphate in human myocardial tissue. Hypertension. 2004 May;43(5):1055-9. Epub 2004 Apr 5.
13. Stavrou BM: Diadenosine polyphosphates: postulated mechanisms mediating the cardiac effects. Curr Med Chem Cardiovasc Hematol Agents. 2003 Jun;1(2):151-69.
14. Davies G, MacAllister RJ, Bogle RG, Vallance P: Effect of diadenosine phosphates on human umbilical vessels: novel platelet-derived vasoconstrictors. Br J Clin Pharmacol. 1995 Aug;40(2):170-2.
15. Tepel M, Lowe S, Nofer JR, Assmann G, Schluter H, Zidek W: Diadenosine polyphosphates regulate cytosolic calcium in human fibroblast cells by interaction with P2x purinoceptors coupled to phospholipase C. Biochim Biophys Acta. 1996 Jun 13;1312(2):145-50.
16. Vahlensieck U, Boknik P, Knapp J, Linck B, Muller FU, Neumann J, Herzig S, Schluter H, Zidek W, Deng MC, Scheld HH, Schmitz W: Negative chronotropic and inotropic effects exerted by diadenosine hexaphosphate (AP6A) via A1-adenosine receptors. Br J Pharmacol. 1996 Nov;119(5):835-44.
17. Gasmi L, McLennan AG, Edwards SW: Neutrophil apoptosis is delayed by the diadenosine polyphosphates, Ap5A and Ap6A: synergism with granulocyte-macrophage colony-stimulating factor. Br J Haematol. 1996 Dec;95(4):637-9.
18. Ogilvie A, Blasius R, Schulze-Lohoff E, Sterzel RB: Adenine dinucleotides: a novel class of signalling molecules. J Auton Pharmacol. 1996 Dec;16(6):325-8.
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. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
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