Record Information
Version1.0
Creation date2015-05-07 20:58:27 UTC
Update date2019-11-26 03:22:08 UTC
Primary IDFDB031082
Secondary Accession Numbers
  • FDB022564
Chemical Information
FooDB NameP1,P4-bis(5'-guanosyl) tetraphosphate
DescriptionP(1),p(4)-bis(5'-guanosyl) tetraphosphate, also known as gp4g or gppppg, is a member of the class of compounds known as (5'->5')-dinucleotides (5'->5')-dinucleotides are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage. P(1),p(4)-bis(5'-guanosyl) tetraphosphate is soluble (in water) and an extremely strong acidic compound (based on its pKa). P(1),p(4)-bis(5'-guanosyl) tetraphosphate can be found in a number of food items such as allium (onion), pasta, rocket salad (sspecies), and vanilla, which makes p(1),p(4)-bis(5'-guanosyl) tetraphosphate a potential biomarker for the consumption of these food products. P(1),p(4)-bis(5'-guanosyl) tetraphosphate exists in all living species, ranging from bacteria to humans. In humans, p(1),p(4)-bis(5'-guanosyl) tetraphosphate is involved in few metabolic pathways, which include azathioprine action pathway, mercaptopurine action pathway, purine metabolism, and thioguanine action pathway. P(1),p(4)-bis(5'-guanosyl) tetraphosphate is also involved in several metabolic disorders, some of which include lesch-nyhan syndrome (LNS), myoadenylate deaminase deficiency, mitochondrial DNA depletion syndrome, and xanthine dehydrogenase deficiency (xanthinuria).
CAS Number4130-19-2
Structure
Thumb
Synonyms
SynonymSource
(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
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC20H28N10O21P4
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
InChI IdentifierInChI=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
Isomeric SMILESNC1=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
Average Molecular Weight868.3858
Monoisotopic Molecular Weight868.038094056
Classification
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:

Biological location:

Source:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0910110030-a6bd659122b84da65d3fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c04b5e08bc949915c2fdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-de8f07c2ed0e9f17f0eeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-0700011090-f69c78a4b50e25f0eb5cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900010000-b766f54c386c57ea4bcdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2915010000-506add7a25f1233ab648JSpectraViewer
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound IDNot Available
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference