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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:13 UTC
HMDB IDHMDB0001340
Secondary Accession Numbers
  • HMDB01340
Metabolite Identification
Common NameDiguanosine tetraphosphate
DescriptionDiguanosine tetraphosphate, also known as GPPPPG or (PPG)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. Diguanosine polyphosphates (GpnGs) are found in human platelets, among a number of dinucleoside polyphosphates, which vary with respect to the number of phosphate groups and the nucleoside moieties; not only diguanosine polyphosphates (GpnG) are found, but also mixed dinucleoside polyphosphates containing one adenosine and one guanosine moiety (ApnG). Diguanosine tetraphosphate is a moderately basic compound (based on its pKa). Diguanosine tetraphosphate exists in all living species, ranging from bacteria to humans. diguanosine tetraphosphate can be converted into guanosine triphosphate and guanosine monophosphate through its interaction with the enzyme bis(5'-nucleosyl)-tetraphosphatase [asymmetrical]. The vasoactive nucleotides that can be detected in human plasma contain shorter (n=2-3) and longer (n=4-6) polyphosphate chains. In humans, diguanosine tetraphosphate is involved in the metabolic disorder called the purine nucleoside phosphorylase deficiency pathway. Outside of the human body, Diguanosine tetraphosphate has been detected, but not quantified in, several different foods, such as pepper (c. pubescens), brassicas, lowbush blueberries, hedge mustards, and silver lindens. This could make diguanosine tetraphosphate a potential biomarker for the consumption of these foods. GpnGs have not yet been characterized so far with respect to their effects on kidney vasculature. Diguanosine tetraphosphate is a diguanosine polyphosphate.
Structure
Data?1582752193
Synonyms
ValueSource
(PPG)2ChEBI
Bis(5'-guanosyl) tetraphosphateChEBI
Bis(guanylyl) diphosphateChEBI
g(5')P4(5')gChEBI
GP4gChEBI
GPPPPGChEBI
Guanosine(5')tetraphospho(5')guanosineChEBI
P1,P4-Bis(5'-guanosyl) tetraphosphateChEBI
Bis(5'-guanosyl) tetraphosphoric acidGenerator
Bis(guanylyl) diphosphoric acidGenerator
P1,P4-Bis(5'-guanosyl) tetraphosphoric acidGenerator
Diguanosine tetraphosphoric acidGenerator
[5-(2-Amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-[[[[5-(2-amino-6-hydroxy-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-hydroxy-phosphoryl]oxy-phosphinic acidHMDB
Chemical FormulaC20H28N10O21P4
Average Molecular Weight868.3858
Monoisotopic Molecular Weight868.038094056
IUPAC Name{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy})phosphinic acid
Traditional Namediguanosine tetraphosphate
CAS Registry Number4130-19-2
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]3O[C@H]([C@H](O)[C@@H]3O)N3C=NC4=C3N=C(N)NC4=O)[C@@H](O)[C@H]2O)C(=O)N1
InChI Identifier
InChI=1S/C20H28N10O21P4/c21-19-25-13-7(15(35)27-19)23-3-29(13)17-11(33)9(31)5(47-17)1-45-52(37,38)49-54(41,42)51-55(43,44)50-53(39,40)46-2-6-10(32)12(34)18(48-6)30-4-24-8-14(30)26-20(22)28-16(8)36/h3-6,9-12,17-18,31-34H,1-2H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H3,21,25,27,35)(H3,22,26,28,36)/t5-,6-,9-,10-,11-,12-,17-,18-/m1/s1
InChI KeyOLGWXCQXRSSQPO-MHARETSRSA-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-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Imidazopyrimidine
  • Purine
  • Pyrimidone
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Pyrimidine
  • Alkyl phosphate
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

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 Solubility11 g/LALOGPS
logP-0.18ALOGPS
logP-5.9ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)0.5ChemAxon
pKa (Strongest Basic)1.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count22ChemAxon
Hydrogen Donor Count12ChemAxon
Polar Surface Area465.33 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity168.95 m³·mol⁻¹ChemAxon
Polarizability68.35 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, Positivesplash10-0udi-0910110030-a6bd659122b84da65d3fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c04b5e08bc949915c2fdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-de8f07c2ed0e9f17f0eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0700011090-f69c78a4b50e25f0eb5cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900010000-b766f54c386c57ea4bcdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2915010000-506add7a25f1233ab648Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
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 IDFDB031082
KNApSAcK IDNot Available
Chemspider ID144813
KEGG Compound IDC01261
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4175
PubChem Compound165186
PDB IDNot Available
ChEBI ID15883
Food Biomarker OntologyNot Available
VMH IDM02671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. van der Giet M, Westhoff T, Cinkilic O, Jankowski J, Schluter H, Zidek W, Tepel M: The critical role of adenosine and guanosine in the affinity of dinucleoside polyphosphates to P(2X)-receptors in the isolated perfused rat kidney. Br J Pharmacol. 2001 Jan;132(2):467-74. [PubMed:11159696 ]
  2. Ralevic V, Jankowski J, Schluter H: Structure-activity relationships of diadenosine polyphosphates (Ap(n)As), adenosine polyphospho guanosines (Ap(n)Gs) and guanosine polyphospho guanosines (Gp(n)Gs) at P2 receptors in the rat mesenteric arterial bed. Br J Pharmacol. 2001 Nov;134(5):1073-83. [PubMed:11682456 ]
  3. Jankowski J, Hagemann J, Tepel M, van Der Giet M, Stephan N, Henning L, Gouni-Berthold I, Sachinidis A, Zidek W, Schluter H: Dinucleotides as growth-promoting extracellular mediators. Presence of dinucleoside diphosphates Ap2A, Ap2G, and Gp2G in releasable granules of platelets. J Biol Chem. 2001 Mar 23;276(12):8904-9. Epub 2000 Dec 13. [PubMed:11115507 ]

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Asymmetrically hydrolyzes Ap4A to yield AMP and ATP. Plays a major role in maintaining homeostasis.
Gene Name:
NUDT2
Uniprot ID:
P50583
Molecular weight:
16829.09
Reactions
Diguanosine tetraphosphate + Water → Guanosine triphosphate + Guanosine monophosphatedetails