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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:23 UTC
HMDB IDHMDB0001454
Secondary Accession Numbers
  • HMDB01454
Metabolite Identification
Common NameGuanosine tetraphosphate adenosine
DescriptionGuanosine tetraphosphate adenosine is a dinucleoside polyphosphate. Dinucleoside polyphosphates are an interesting group of signalling molecules that control numerous physiological functions. Diadenosine compounds, with a backbone of anything from two to seven phosphates, are known to occur naturally. Some of them have been isolated from cerebral nerve terminals and, acting via nucleoside (P1), nucleotide (P2), or dinucleotide receptors, can affect central nervous system function. Many of them have been isolated from human blood platelet secretory granules and are potentially involved in haemostatic mechanisms and peripheral control of vascular tone. Many visceral organs respond to the application of adenine dinucleotides and, although they act on receptors in the periphery that can be mainly defined as either P1 or P2, evidence is now accumulating for discrete dinucleotide receptors. In the periphery, adenine dinucleotides can be potent agonists, with diverse functions, causing contraction or relaxation of smooth muscle. Many P2X receptor proteins and P2Y receptors have been cloned and adenine dinucleotides have a variable pharmacological profile at these receptors and may be useful tools for characterising subtypes of P2X and P2Y receptors. Many extracellular roles of diadenosine polyphosphates are emerging as yet increasingly important, natural ligands for a plethora of structurally diverse mononucleotide and dinucleotide receptors. (PMID: 12772275 , 7767329 ).
Structure
Data?1582752203
Synonyms
ValueSource
a(5')P4(5')gChEBI
Guanosine tetraphosphoric acid adenosineGenerator
Guanosine 5'-(pentahydrogen tetraphosphate), 5'->3'-ester with adenosineHMDB
AP4gHMDB
Adenosine 5'-p(1)-tetraphosphate-p(4)-5'''-guanosineHMDB
p(1)-(5'-Adenosyl),p(4)-(5'-guanosyl) tetraphosphoric acidGenerator
Chemical FormulaC20H28N10O20P4
Average Molecular Weight852.3864
Monoisotopic Molecular Weight852.043179434
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-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 Name[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxyphosphinic acid
CAS Registry Number100849-67-0
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C20H28N10O20P4/c21-14-8-15(24-3-23-14)29(4-25-8)18-12(33)10(31)6(46-18)1-44-51(36,37)48-53(40,41)50-54(42,43)49-52(38,39)45-2-7-11(32)13(34)19(47-7)30-5-26-9-16(30)27-20(22)28-17(9)35/h3-7,10-13,18-19,31-34H,1-2H2,(H,36,37)(H,38,39)(H,40,41)(H,42,43)(H2,21,23,24)(H3,22,27,28,35)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChI KeySJXJAXXRDJWRCR-INFSMZHSSA-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
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Alkyl phosphate
  • Imidolactam
  • Phosphoric acid ester
  • Monosaccharide
  • Organic phosphoric acid derivative
  • N-substituted imidazole
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.5 g/LALOGPS
logP-0.4ALOGPS
logP-8.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)0.6ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area449.65 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity167.1 m³·mol⁻¹ChemAxon
Polarizability68.66 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0910100010-fde0bd6ae0e95ff3c44bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0900000000-2b534cc4ec28ba87b832Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-0900000000-1b5013a2ec180f8123ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0900010050-1885a33b078973c8b2c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f89-0900010000-2f97f5c2ce1f7f3e47c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uyi-1925100000-b3aeb882f1b1b9344e5cSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022633
KNApSAcK IDNot Available
Chemspider ID8947177
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10771862
PDB IDNot Available
ChEBI ID52968
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jankowski J, Grosse-Huttmann P, Zidek W, Schluter H: Identification of dinucleoside polyphosphates by matrix-assisted laser desorption/ionisation post-source decay mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(11):1189-94. [PubMed:12772275 ]
  2. Chen ZP, Levy A, Lightman SL: Nucleotides as extracellular signalling molecules. J Neuroendocrinol. 1995 Feb;7(2):83-96. [PubMed:7767329 ]