Adenosine 5'-diphosphate glucose (CHEM023563)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:08:54 UTC
Update Date2016-11-09 01:17:44 UTC
Accession NumberCHEM023563
Identification
Common NameAdenosine 5'-diphosphate glucose
ClassSmall Molecule
DescriptionAn ADP-aldose having alpha-D-glucopyranose as the sugar moiety.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Adenosine diphosphate glucoseChEBI
Adenosine diphosphoglucoseChEBI
Adenosine pyrophosphateglucoseChEBI
ADPGChEBI
ADPglucoseChEBI
ADP-alpha-D-GlucoseKegg
Adenosine diphosphoric acid glucoseGenerator
ADP-a-D-GlucoseGenerator
ADP-Α-D-glucoseGenerator
Adenosine 5'-(trihydrogen diphosphate) glucopyranosyl esterHMDB
Adenosine 5'-(trihydrogen diphosphate) p'-alpha-delta-glucopyranosyl esterHMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-D-glucosyl esterHMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-delta-glucosyl esterHMDB
Adenosine 5'-diphosphoglucoseHMDB
Adenosine 5'-pyrophosphate a-delta-glucosyl esterHMDB
Adenosine 5'-pyrophosphate alpha-D-glucosyl esterHMDB
Adenosine 5'-pyrophosphate alpha-delta-glucosyl esterHMDB
Adenosine 5'-pyrophosphate glucosyl esterHMDB
Adenosine 5'-pyrophosphate mono-D-glucosyl esterHMDB
Adenosine 5'-pyrophosphate mono-delta-glucosyl esterHMDB
Adenosine diphosphate D-glucoseHMDB
Adenosine pyrophosphate-glucoseHMDB
Adenosine-5'-diphosphate-glucoseHMDB
ADP-D-GlucoseHMDB
ADP GlucoseHMDB
Diphosphate glucose, adenosineHMDB
Diphosphoglucose, adenosineHMDB
Glucose, ADPHMDB
Glucose, adenosine diphosphateHMDB
Pyrophosphateglucose, adenosineHMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-alpha-D-glucosyl esterHMDB
Adenosine 5'-(trihydrogen pyrophosphate) mono-α-D-glucosyl esterHMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-D-glucosyl esterHMDB
Adenosine 5’-(trihydrogen pyrophosphate) mono-α-D-glucosyl esterHMDB
Adenosine 5’-diphosphoglucoseHMDB
Adenosine 5’-pyrophosphate mono-D-glucosyl esterHMDB
ADP-GlucoseHMDB
Chemical FormulaC16H25N5O15P2
Average Molecular Mass589.342 g/mol
Monoisotopic Mass589.082 g/mol
CAS Registry Number2140-58-1
IUPAC Name[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Nameadp glucose
SMILESNC1=C2N=CN(C3OC(COP(O)(=O)OP(O)(=O)OC4OC(CO)C(O)C(O)C4O)C(O)C3O)C2=NC=N1
InChI IdentifierInChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)
InChI KeyWFPZSXYXPSUOPY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine nucleotide sugars
Direct ParentPurine nucleotide sugars
Alternative Parents
Substituents
  • Purine nucleotide sugar
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside monophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Oxane
  • Phosphoric acid ester
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Polyol
  • Oxacycle
  • Organic oxide
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Organonitrogen compound
  • Primary alcohol
  • Primary amine
  • Organooxygen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.84 g/LALOGPS
logP-1.8ALOGPS
logP-6.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)3.99ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area311.75 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.09 m³·mol⁻¹ChemAxon
Polarizability48.69 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05di-5941580000-aa3b11c510a971dd2baeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05be-8925707000-bdd8b43e72abaa64441bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("ADP-glucose,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, positivesplash10-0006-0000290000-7f66f6e8af24e4839d36Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 30V, positivesplash10-004l-0000950000-739c8280d86a2f6f3b3bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 32V, negativesplash10-002k-9248080000-875881d0c025c30eb244Spectrum
LC-MS/MSLC-MS/MS Spectrum - NA , negativesplash10-003r-3900000000-64717800131918b409d1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-000i-1901000000-e41db8583774d0cca66dSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-004i-0000940000-0f0b4d7b3da79f054155Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000900000-c6a92771658ee7a74bb5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-004i-0401900000-e9c970aa89843c279822Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910520000-894488255e0d2059a6caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-af7d8977d3d229ea73eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-39c6318a5ada8cb3ebb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1901470000-134113735239a2586876Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1901000000-48fb3c4c1d3e3f084d3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0563-3900000000-f9f285dafe2da95e8009Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000090000-494b86dfa2b4e6fc0ac1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-5421970000-431fd452ea842be1eb27Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-2922610000-bc7320a1bf5a6bf0dc76Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-46811e8e339262e18415Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-0841490000-f709931b7e24d70dc4f3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2921000000-17d11c3948611bf9ff8bSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB01774
HMDB IDHMDB0006557
FooDB IDFDB112366
Phenol Explorer IDNot Available
KNApSAcK IDC00007354
BiGG ID35161
BioCyc IDADP-D-GLUCOSE
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID15642
ChEBI ID15751
PubChem Compound ID16500
Kegg Compound IDC00498
YMDB IDNot Available
ECMDB IDECMDB06557
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=15951568
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23292602
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23537328
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24762788
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25133777
6. Tamura, Kiminori; Morozumi, Manami; Yoshino, Hiroshi; Noda, Yutaka; Suzuki, Morio. Nucleotide anhydrides. Ger. Offen. (1972), 16 pp. CODEN: GWXXBX DE 2038262 19720203 CAN 76:99993 AN 1972:99993
7. Tiessen A, Nerlich A, Faix B, Hummer C, Fox S, Trafford K, Weber H, Weschke W, Geigenberger P: Subcellular analysis of starch metabolism in developing barley seeds using a non-aqueous fractionation method. J Exp Bot. 2012 Mar;63(5):2071-87. doi: 10.1093/jxb/err408. Epub 2011 Dec 26.
8. Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: Microbial volatile emissions promote accumulation of exceptionally high levels of starch in leaves in mono- and dicotyledonous plants. Plant Cell Physiol. 2010 Oct;51(10):1674-93. doi: 10.1093/pcp/pcq126. Epub 2010 Aug 24.
9. Szecowka M, Osorio S, Obata T, Araujo WL, Rohrmann J, Nunes-Nesi A, Fernie AR: Decreasing the mitochondrial synthesis of malate in potato tubers does not affect plastidial starch synthesis, suggesting that the physiological regulation of ADPglucose pyrophosphorylase is context dependent. Plant Physiol. 2012 Dec;160(4):2227-38. doi: 10.1104/pp.112.204826. Epub 2012 Oct 12.
10. Uhlmann NK, Beckles DM: Storage products and transcriptional analysis of the endosperm of cultivated wheat and two wild wheat species. J Appl Genet. 2010;51(4):431-47. doi: 10.1007/BF03208873.
11. Li J, Baroja-Fernandez E, Bahaji A, Munoz FJ, Ovecka M, Montero M, Sesma MT, Alonso-Casajus N, Almagro G, Sanchez-Lopez AM, Hidalgo M, Zamarbide M, Pozueta-Romero J: Enhancing sucrose synthase activity results in increased levels of starch and ADP-glucose in maize (Zea mays L.) seed endosperms. Plant Cell Physiol. 2013 Feb;54(2):282-94. doi: 10.1093/pcp/pcs180. Epub 2013 Jan 3.
12. Bejar CM, Ballicora MA, Iglesias AA, Preiss J: ADPglucose pyrophosphorylase's N-terminus: structural role in allosteric regulation. Biochem Biophys Res Commun. 2006 Apr 28;343(1):216-21. Epub 2006 Mar 2.
13. Baroja-Fernandez E, Munoz FJ, Montero M, Etxeberria E, Sesma MT, Ovecka M, Bahaji A, Ezquer I, Li J, Prat S, Pozueta-Romero J: Enhancing sucrose synthase activity in transgenic potato (Solanum tuberosum L.) tubers results in increased levels of starch, ADPglucose and UDPglucose and total yield. Plant Cell Physiol. 2009 Sep;50(9):1651-62. doi: 10.1093/pcp/pcp108. Epub 2009 Jul 16.
14. Haferkamp I: The diverse members of the mitochondrial carrier family in plants. FEBS Lett. 2007 May 25;581(12):2375-9. Epub 2007 Feb 26.
15. Comparot-Moss S, Denyer K: The evolution of the starch biosynthetic pathway in cereals and other grasses. J Exp Bot. 2009;60(9):2481-92. doi: 10.1093/jxb/erp141.
16. Ezquer I, Li J, Ovecka M, Baroja-Fernandez E, Munoz FJ, Montero M, Diaz de Cerio J, Hidalgo M, Sesma MT, Bahaji A, Etxeberria E, Pozueta-Romero J: A suggested model for potato MIVOISAP involving functions of central carbohydrate and amino acid metabolism, as well as actin cytoskeleton and endocytosis. Plant Signal Behav. 2010 Dec;5(12):1638-41. Epub 2010 Dec 1.
17. Baroja-Fernandez E, Etxeberria E, Munoz FJ, Moran-Zorzano MT, Alonso-Casajus N, Gonzalez P, Pozueta-Romero J: An important pool of sucrose linked to starch biosynthesis is taken up by endocytosis in heterotrophic cells. Plant Cell Physiol. 2006 Apr;47(4):447-56. Epub 2006 Jan 24.
18. Fettke J, Malinova I, Albrecht T, Hejazi M, Steup M: Glucose-1-phosphate transport into protoplasts and chloroplasts from leaves of Arabidopsis. Plant Physiol. 2011 Apr;155(4):1723-34. doi: 10.1104/pp.110.168716. Epub 2010 Nov 29.
19. Wiedemuth K, Muller J, Kahlau A, Amme S, Mock HP, Grzam A, Hell R, Egle K, Beschow H, Humbeck K: Successive maturation and senescence of individual leaves during barley whole plant ontogeny reveals temporal and spatial regulation of photosynthetic function in conjunction with C and N metabolism. J Plant Physiol. 2005 Nov;162(11):1226-36.
20. Nagai YS, Sakulsingharoj C, Edwards GE, Satoh H, Greene TW, Blakeslee B, Okita TW: Control of starch synthesis in cereals: metabolite analysis of transgenic rice expressing an up-regulated cytoplasmic ADP-glucose pyrophosphorylase in developing seeds. Plant Cell Physiol. 2009 Mar;50(3):635-43. doi: 10.1093/pcp/pcp021. Epub 2009 Feb 10.
21. Thorneycroft D, Hosein F, Thangavelu M, Clark J, Vizir I, Burrell MM, Ainsworth C: Characterization of a gene from chromosome 1B encoding the large subunit of ADPglucose pyrophosphorylase from wheat: evolutionary divergence and differential expression of Agp2 genes between leaves and developing endosperm. Plant Biotechnol J. 2003 Jul;1(4):259-70.
22. Moran-Zorzano MT, Alonso-Casajus N, Munoz FJ, Viale AM, Baroja-Fernandez E, Eydallin G, Pozueta-Romero J: Occurrence of more than one important source of ADPglucose linked to glycogen biosynthesis in Escherichia coli and Salmonella. FEBS Lett. 2007 Sep 18;581(23):4423-9. Epub 2007 Aug 15.
23. Smith AM: Prospects for increasing starch and sucrose yields for bioethanol production. Plant J. 2008 May;54(4):546-58. doi: 10.1111/j.1365-313X.2008.03468.x.
24. Lunn JE, Feil R, Hendriks JH, Gibon Y, Morcuende R, Osuna D, Scheible WR, Carillo P, Hajirezaei MR, Stitt M: Sugar-induced increases in trehalose 6-phosphate are correlated with redox activation of ADPglucose pyrophosphorylase and higher rates of starch synthesis in Arabidopsis thaliana. Biochem J. 2006 Jul 1;397(1):139-48.
25. Eydallin G, Moran-Zorzano MT, Munoz FJ, Baroja-Fernandez E, Montero M, Alonso-Casajus N, Viale AM, Pozueta-Romero J: An Escherichia coli mutant producing a truncated inactive form of GlgC synthesizes glycogen: further evidences for the occurrence of various important sources of ADPglucose in enterobacteria. FEBS Lett. 2007 Sep 18;581(23):4417-22. Epub 2007 Aug 15.
26. Asencion Diez MD, Aleanzi MC, Iglesias AA, Ballicora MA: A novel dual allosteric activation mechanism of Escherichia coli ADP-glucose pyrophosphorylase: the role of pyruvate. PLoS One. 2014 Aug 7;9(8):e103888. doi: 10.1371/journal.pone.0103888. eCollection 2014.