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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:58:16 UTC
HMDB IDHMDB0001501
Secondary Accession Numbers
  • HMDB01501
Metabolite Identification
Common NameGuanosine diphosphate adenosine
DescriptionGuanosine diphosphate adenosine is a dinucleoside polyphosphate. Dinucleoside polyphosphates are an interesting group of signalling molecules that control numerous physiological functions. Diadenosine compounds, with a backbone of anything from two to seven phosphates, are known to occur naturally. Some of them have been isolated from cerebral nerve terminals and, acting via nucleoside (P1), nucleotide (P2), or dinucleotide receptors, can affect central nervous system function. Many of them have been isolated from human blood platelet secretory granules and are potentially involved in haemostatic mechanisms and peripheral control of vascular tone. Many visceral organs respond to the application of adenine dinucleotides and, although they act on receptors in the periphery that can be mainly defined as either P1 or P2, evidence is now accumulating for discrete dinucleotide receptors. In the periphery, adenine dinucleotides can be potent agonists, with diverse functions, causing contraction or relaxation of smooth muscle. Many P2X receptor proteins and P2Y receptors have been cloned and adenine dinucleotides have a variable pharmacological profile at these receptors and may be useful tools for characterising subtypes of P2X and P2Y receptors. Many extracellular roles of diadenosine polyphosphates are emerging as yet increasingly important, natural ligands for a plethora of structurally diverse mononucleotide and dinucleotide receptors. (PMID: 12772275 , 7767329 ).
Structure
Data?1582752206
Synonyms
ValueSource
Guanosine diphosphoric acid adenosineGenerator
{[(2R,3R,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(6-hydroxy-2-imino-3,9-dihydro-2H-purin-9-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonateHMDB
Chemical FormulaC20H26N10O14P2
Average Molecular Weight692.4266
Monoisotopic Molecular Weight692.110518614
IUPAC Name{[(2R,3R,4R,5R)-4-[({[(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]-2-(6-amino-9H-purin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3R,4R,5R)-4-({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry Number65331-78-4
SMILES
NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C20H26N10O14P2/c21-14-8-15(24-3-23-14)29(4-25-8)19-13(43-45(35,36)37)12(6(1-31)41-19)44-46(38,39)40-2-7-10(32)11(33)18(42-7)30-5-26-9-16(30)27-20(22)28-17(9)34/h3-7,10-13,18-19,31-33H,1-2H2,(H,38,39)(H2,21,23,24)(H2,35,36,37)(H3,22,27,28,34)/t6-,7-,10-,11-,12-,13-,18-,19-/m1/s1
InChI KeyLHSVDZHIRYSVJP-INFSMZHSSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as (3'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (3'->5')-phosphodiester linkage.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
Class(3'->5')-dinucleotides and analogues
Sub Class(3'->5')-dinucleotides
Direct Parent(3'->5')-dinucleotides
Alternative Parents
Substituents
  • (3'->5')-dinucleotide
  • Purine ribonucleoside monophosphate
  • Pentose-5-phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purine
  • Imidazopyrimidine
  • Pyrimidone
  • Dialkyl phosphate
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Vinylogous amide
  • Tetrahydrofuran
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Organoheterocyclic compound
  • Oxacycle
  • Azacycle
  • Amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Primary alcohol
  • Primary amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.67 g/LALOGPS
logP-1.5ALOGPS
logP-7.2ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.47ChemAxon
pKa (Strongest Basic)4.87ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area356.59 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity145.35 m³·mol⁻¹ChemAxon
Polarizability58.47 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+233.76532859911
AllCCS[M-H]-225.44232859911
DeepCCS[M-2H]-265.64730932474
DeepCCS[M+Na]+239.94430932474
AllCCS[M+H]+233.832859911
AllCCS[M+H-H2O]+233.232859911
AllCCS[M+NH4]+234.332859911
AllCCS[M+Na]+234.432859911
AllCCS[M-H]-225.432859911
AllCCS[M+Na-2H]-227.132859911
AllCCS[M+HCOO]-229.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Guanosine diphosphate adenosineNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O5032.5Standard polar33892256
Guanosine diphosphate adenosineNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O3636.2Standard non polar33892256
Guanosine diphosphate adenosineNC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@@H](CO)O[C@H]([C@@H]2OP(O)(O)=O)N2C=NC3=C(N)N=CN=C23)[C@@H](O)[C@H]1O6400.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (Non-derivatized) - 70eV, Positivesplash10-01r2-8243907000-35e98bb9774530c7cee42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_5) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_6) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_7) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_8) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_9) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_10) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_11) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_12) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_13) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_14) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_15) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Guanosine diphosphate adenosine GC-MS (TMS_2_16) - 70eV, PositiveNot Available2021-10-18Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 10V, Positive-QTOFsplash10-0f79-0900010000-2517134062e69ae041352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 20V, Positive-QTOFsplash10-0f79-0900000000-f9331fb92caae2533e9d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 40V, Positive-QTOFsplash10-0f79-0900000000-41b921abfcb64a5674152017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 10V, Negative-QTOFsplash10-0f9x-4901106000-3ea4fd80696ba1393eaa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 20V, Negative-QTOFsplash10-0fai-2900000000-6237eb6ab6c696f039ed2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 40V, Negative-QTOFsplash10-0059-9800000000-fdac5459a7161cff729b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 10V, Positive-QTOFsplash10-0udi-0900014000-60e29d160fae08185d9e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 20V, Positive-QTOFsplash10-0udi-0900101000-0a9495b68718f2fd76c32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 40V, Positive-QTOFsplash10-0udi-0911100000-27a489fb4fc30990db582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 10V, Negative-QTOFsplash10-0006-0000009000-ff71e0461774d8b6fea52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 20V, Negative-QTOFsplash10-05i3-2100209000-8bb9c47b6d7ec520858e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Guanosine diphosphate adenosine 40V, Negative-QTOFsplash10-0059-6864219000-89d8fda7e8e5260455bf2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB022659
KNApSAcK IDNot Available
Chemspider ID8637730
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10462318
PDB IDNot Available
ChEBI ID168201
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jankowski J, Grosse-Huttmann P, Zidek W, Schluter H: Identification of dinucleoside polyphosphates by matrix-assisted laser desorption/ionisation post-source decay mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(11):1189-94. [PubMed:12772275 ]
  2. Chen ZP, Levy A, Lightman SL: Nucleotides as extracellular signalling molecules. J Neuroendocrinol. 1995 Feb;7(2):83-96. [PubMed:7767329 ]