P1,P4-Bis(5'-guanosyl) tetraphosphate (ECMDB21264) (M2MDB001671)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-07-30 14:55:09 -0600
Update Date2015-06-03 17:21:02 -0600
Secondary Accession Numbers
  • ECMDB21264
Identification
Name:P1,P4-Bis(5'-guanosyl) tetraphosphate
DescriptionDiguanosine tetraphosphate is a diguanosine polyphosphate. It consists of two guanosines joined by a chain of 4 phosphates.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (ppG)2
  • Bis(5'-guanosyl) tetraphosphate
  • Bis(5'-guanosyl) tetraphosphoric acid
  • Bis(guanylyl) diphosphate
  • Bis(guanylyl) diphosphoric acid
  • Diguanosine tetraphosphate
  • Diguanosine tetraphosphoric acid
  • G(5')P4(5')G
  • GP4G
  • GppppG
  • Guanosine(5')tetraphospho(5')guanosine
  • P1,P4-bis(5'-guanosyl) tetrahydrogen tetraphosphate
  • P1,P4-Bis(5'-guanosyl) tetrahydrogen tetraphosphoric acid
  • P1,P4-Bis(5'-guanosyl) tetraphosphate
  • P1,P4-Bis(5'-guanosyl) tetraphosphoric acid
  • [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-phosphinate
  • [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 acid
Chemical Formula:C20H28N10O21P4
Weight:Average: 868.3858
Monoisotopic: 868.038094056
InChI Key:OLGWXCQXRSSQPO-MHARETSRSA-N
InChI: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
CAS number:4130-19-2
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 IUPAC Name:diguanosine tetraphosphate
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
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
Physical Properties
State:Solid
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
P1,P4-Bis(5'-guanosyl) tetraphosphate + Water >2 Guanosine diphosphate +2 Hydrogen ion
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910110030-a6bd659122b84da65d3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c04b5e08bc949915c2fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-de8f07c2ed0e9f17f0eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0700011090-f69c78a4b50e25f0eb5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900010000-b766f54c386c57ea4bcdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2915010000-506add7a25f1233ab648View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000020-b1759ae61121c874c253View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000020-ad098ec0ac59f44f6bc6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-0900100000-91fc747e55e03728ef79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0000000090-cb93d23c88ced7dae5b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0400020390-175e627e05080096994aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbc-0510390050-039fd4c9138a3432cc17View in MoNA
MSMass Spectrum (Electron Ionization)Not AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID15883
HMDB IDHMDB01340
Pubchem Compound ID165186
Kegg IDC01261
ChemSpider ID144813
Wikipedia IDNot Available
BioCyc IDCPD-609
EcoCyc IDCPD-609

Enzymes

Protein Details
1. Bis(5'-nucleosyl)-tetraphosphatase [symmetrical]
General function:
Involved in bis(5'-nucleosyl)-tetraphosphatase (symmetrical) activity
Specific function:
Hydrolyzes diadenosine 5',5'''-P1,P4-tetraphosphate to yield ADP
Gene Name:
apaH
Uniprot ID:
P05637
Molecular weight:
31296
Reactions
P(1),P(4)-bis(5'-adenosyl) tetraphosphate + H(2)O = 2 ADP.