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Showing Compound Guanosine diphosphate (FDB022487)

Record Information
Version1.0
Creation date2011-09-21 00:14:47 UTC
Update date2020-09-17 15:40:24 UTC
Primary IDFDB022487
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGuanosine diphosphate
DescriptionGuanosine diphosphate, also known as 5'-GDP or 5'-diphosphate, 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 diphosphate is a moderately basic compound (based on its pKa). Guanosine diphosphate exists in all living species, ranging from bacteria to humans. In humans, guanosine diphosphate is involved in intracellular signalling through adenosine receptor A2B and adenosine. Outside of the human body, Guanosine diphosphate has been detected, but not quantified in, several different foods, such as devilfish, java plums, green beans, almonds, and orange mints. This could make guanosine diphosphate a potential biomarker for the consumption of these foods. A purine ribonucleoside 5'-diphosphate resulting from the formal condensation of the hydroxy group at the 5' position of guanosine with pyrophosphoric acid.
CAS Number146-91-8
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Guanosine 5'-diphosphateChEBI
Guanosine 5'-diphosphoric acidGenerator
Guanosine diphosphoric acidGenerator
5'-GDPHMDB
GDPHMDB
Guanosine 5'-(trihydrogen pyrophosphate)HMDB
Guanosine 5'-pyrophosphateHMDB
Guanosine mono(trihydrogen diphosphate)HMDB
Guanosine pyrophosphateHMDB
Guanosine-5'-diphosphateHMDB
Guanosine-diphosphateHMDB
PpGHMDB
5'-Diphosphate, guanosineHMDB
Diphosphate, guanosine 5'-trihydrogenHMDB
Guanosine 5' diphosphateHMDB
Guanosine 5' trihydrogen diphosphateHMDB
5'-Trihydrogen diphosphate, guanosineHMDB
Diphosphate, guanosineHMDB
Guanosine 5'-trihydrogen diphosphateHMDB
Guanosine 5'-(trihydrogen pyroate)HMDB
Guanosine 5'-diateChEBI
Guanosine 5'-diic acidGenerator
Guanosine 5'-pyroateHMDB
Guanosine diateChEBI
Guanosine diic acidGenerator
Guanosine mono(trihydrogen diate)HMDB
Guanosine pyroateHMDB
Guanosine-5'-diateHMDB
guanosine-5'-diphosphatehmdb
Guanosine-diateHMDB
guanosine-diphosphatehmdb
ppGhmdb
Predicted Properties
PropertyValueSource
Water Solubility4.44 g/LALOGPS
logP-1.5ALOGPS
logP-3.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.71ChemAxon
pKa (Strongest Basic)2.55ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area248.28 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.93 m³·mol⁻¹ChemAxon
Polarizability34.74 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC10H15N5O11P2
IUPAC name[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
InChI IdentifierInChI=1S/C10H15N5O11P2/c11-10-13-7-4(8(18)14-10)12-2-15(7)9-6(17)5(16)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,16-17H,1H2,(H,22,23)(H2,19,20,21)(H3,11,13,14,18)/t3-,5-,6-,9-/m1/s1
InChI KeyQGWNDRXFNXRZMB-UUOKFMHZSA-N
Isomeric SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]2O)C(=O)N1
Average Molecular Weight443.2005
Monoisotopic Molecular Weight443.024329371
Classification
Description 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 diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-diol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Organooxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Amine
  • Organic oxygen compound
  • Primary amine
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSGuanosine diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-5930200000-bdc0893316c12636a495Spectrum
Predicted GC-MSGuanosine diphosphate, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0229-6393250000-a57b7f18975223fa888cSpectrum
Predicted GC-MSGuanosine diphosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udl-0900600000-5c7173a5771dfefadc5e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0900000000-d38af29994fa5108c3312012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0udi-0900000000-3072d857dcc8a1b2cbaa2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-0kdi-5901100000-24a5c807e53370f01d0c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0900000000-6399eaf97235815c4cb72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0udi-0900000000-80f8e0b42526cc03fef42021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0pdl-2902100000-027fb059218f84756c352021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0pdl-2902200000-876f01fe6b2be177ac752021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-0pdl-3902100000-054557b6d17ed830f7e52021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9600000000-2f85040f9b280383ec8a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-054o-5904800000-e39f64dcf91afa1444982021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-cdce5e7d8986462632b22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0kdi-5901100000-ba4bded631640c110a562021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0911300000-fcd49d8a5e9d3dc3f9332016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ded96f0f499982ac1ab02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-ac93e95f54842f42e2732016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-0900800000-1ed1199fdace4d1b4d802016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zir-3900000000-b9aeef613c34fe99a48c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9200000000-f630c9237e72a76d3d632016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900200000-fa2d42f6050d9ab601192021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-ed3d09503a04c850d5952021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0900000000-19a5699334c495daa4e52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0001900000-7b9b9276c5e39c703f8c2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9202300000-fa0fbdc8c265ee49a3712021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-278ab542160fff8402562021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID8630
ChEMBL IDCHEMBL384759
KEGG Compound IDC00035
Pubchem Compound ID8977
Pubchem Substance IDNot Available
ChEBI ID17552
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01201
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33599
KNApSAcK IDNot Available
HET IDGDP
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGDP
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
Enzymes
NameGene NameUniProt ID
Rho-related GTP-binding protein RhoURHOUQ7L0Q8
Guanine nucleotide-binding protein G(s) subunit alpha isoforms shortGNASP63092
Guanine nucleotide-binding protein G(q) subunit alphaGNAQP50148
Uridine-cytidine kinase-like 1UCKL1Q9NWZ5
ENTPD4 proteinENTPD4Q8NE73
Ribonucleoside-diphosphate reductase large subunitRRM1P23921
Polyribonucleotide nucleotidyltransferase 1, mitochondrialPNPT1Q8TCS8
Alpha-(1,3)-fucosyltransferaseFUT9Q9Y231
Alpha-1,3/1,6-mannosyltransferase ALG2ALG2Q9H553
Dolichol-phosphate mannosyltransferaseDPM1O60762
GDP-mannose 4,6 dehydrataseGMDSO60547
Chitobiosyldiphosphodolichol beta-mannosyltransferaseALG1Q9BT22
Guanylate kinaseGUK1Q16774
Rho guanine nucleotide exchange factor 1ARHGEF1Q92888
VinexinSORBS3O60504
Guanine nucleotide-binding protein subunit alpha-11GNA11P29992
Guanine nucleotide-binding protein G(t) subunit alpha-1GNAT1P11488
Lysophosphatidic acid receptor 2LPAR2Q9HBW0
Protein RCC2RCC2Q9P258
Protein very KINDKNDC1Q76NI1
Galactoside 2-alpha-L-fucosyltransferase 2FUT2Q10981
Galactoside 2-alpha-L-fucosyltransferase 1FUT1P19526
GDP-L-fucose synthaseTSTA3Q13630
Alpha-(1,6)-fucosyltransferaseFUT8Q9BYC5
Nucleoside diphosphate kinaseNME4A2IDD0
GDP-fucose protein O-fucosyltransferase 2POFUT2Q9Y2G5
Pathways
NameSMPDB LinkKEGG Link
Citric Acid CycleSMP00057 map00020
GluconeogenesisSMP00128 map00010
Purine MetabolismSMP00050 map00230
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference