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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2017-12-07 15:44:14 UTC
HMDB IDHMDB0059638
Secondary Accession Numbers
  • HMDB59638
Metabolite Identification
Common NameGuanosine 3',5'-bis(diphosphate)
DescriptionGuanosine-5',3'-tetraphosphate, also known as tetraphosphate, guanosine, belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. Guanosine-5',3'-tetraphosphate is soluble (in water) and a moderately acidic compound (based on its pKa).
Structure
Thumb
Synonyms
ValueSource
Guanosine 3'-diphosphate 5'-diphosphateChEBI
Guanosine 5'-diphosphate,3'-diphosphateChEBI
GUANOSINE-5',3'-tetraphosphATEChEBI
Guanosine 3'-diphosphoric acid 5'-diphosphoric acidGenerator
Guanosine 3',5'-bis(diphosphoric acid)Generator
Guanosine 5'-diphosphoric acid,3'-diphosphoric acidGenerator
GUANOSINE-5',3'-tetraphosphoric acidGenerator
3'-Diphosphate 5'-diphosphate, guanosineMeSH
5'-Diphosphate 3'-diphosphate, guanosineMeSH
Guanosine tetraphosphateMeSH
Guanosine 5'-diphosphate 3'-diphosphateMeSH
Tetraphosphate, guanosineMeSH
3'-Diphosphate, guanosine 5'-diphosphateMeSH
5'-Diphosphate, guanosine 3'-diphosphateMeSH
Guanosine 3' diphosphate 5' diphosphateMeSH
Guanosine 5' diphosphate 3' diphosphateMeSH
Chemical FormulaC10H17N5O17P4
Average Molecular Weight603.1603
Monoisotopic Molecular Weight602.956990191
IUPAC Name{[hydroxy({[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-3-yl]oxy})phosphoryl]oxy}phosphonic acid
Traditional Name{hydroxy[(2R,3S,4R,5R)-4-hydroxy-2-({[hydroxy(phosphonooxy)phosphoryl]oxy}methyl)-5-(6-hydroxy-2-imino-3H-purin-9-yl)oxolan-3-yl]oxyphosphoryl}oxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@]1(COP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C=NC3=C2NC(=N)N=C3O)[C@]([H])(O)[C@]1([H])OP(O)(=O)OP(O)(O)=O
InChI Identifier
InChI=1S/C10H17N5O17P4/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6(30-36(26,27)32-34(21,22)23)3(29-9)1-28-35(24,25)31-33(18,19)20/h2-3,5-6,9,16H,1H2,(H,24,25)(H,26,27)(H2,18,19,20)(H2,21,22,23)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1
InChI KeyBUFLLCUFNHESEH-UUOKFMHZSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as purine ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentPurine ribonucleoside diphosphates
Alternative Parents
Substituents
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Tetrahydrofuran
  • Vinylogous amide
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Hydrocarbon derivative
  • Amine
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Role

Industrial application:

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 Solubility10.3 g/LALOGPS
logP-0.5ALOGPS
logP-3.9ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.46ChemAxon
pKa (Strongest Basic)7.15ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area342.33 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity118.69 m³·mol⁻¹ChemAxon
Polarizability44.68 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-4903440000-3e191d1a58e267ff9c41View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-8252953000-fd50d9797f6f347aea0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900251000-bee48e0fb5019193ebb1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900110000-1afec092079feefa49a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-1900000000-a38786c52bb589355d91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900026000-a8f89e925338c7ff167dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ke9-4900000000-9b838d812b5a59d56595View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9400000000-7ec14f477759ced2651fView in MoNA
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
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID388557
KEGG Compound IDC01228
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound439450
PDB IDG4P
ChEBI ID17633
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in pyrophosphatase activity
Specific function:
Phosphodiesterase (PDE) that has higher activity toward cAMP than cGMP, as substrate. Plays a role in cell proliferation, is able to induce cell motility and acts as a negative regulator of NME1.
Gene Name:
PRUNE
Uniprot ID:
Q86TP1
Molecular weight:
50199.04
Reactions
Guanosine 3'-diphosphate 5'-triphosphate + Water → Guanosine 3',5'-bis(diphosphate) + Phosphoric aciddetails
General function:
Not Available
Specific function:
ppGpp hydrolyzing enzyme involved in starvation response.
Gene Name:
HDDC3
Uniprot ID:
Q8N4P3
Molecular weight:
15732.745
Reactions
Guanosine 3',5'-bis(diphosphate) + Water → Guanosine diphosphate + Pyrophosphatedetails