Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110500
Identification
Name: ADP-α-D-glucose
Description:A nucleotide-sugar oxoanion resutling from the deprotonation of both free OH groups of the diphosphate group of ADP α-D-glucoside.
Structure
Thumb
Synonyms:
  • adenosine diphosphate glucose
  • ADP-glucose
  • ADP-D-glucose
Chemical Formula: C16H23N5O15P2
Average Molecular Weight: 587.33
Monoisotopic Molecular Weight: 589.08223818
InChI Key: WFPZSXYXPSUOPY-ROYWQJLOSA-L
InChI: InChI=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)/p-2/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1
CAS number: 2140-58-1
IUPAC Name:adenosine 5'-[3-(α-D-glucopyranosyl) diphosphate]
Traditional IUPAC Name: adp glucose
SMILES:C(C1(C(C(C(C(O1)OP(OP(OCC2(OC(C(C2O)O)N3(C4(N=CN=C(N)C(N=C3)=4))))(=O)[O-])(=O)[O-])O)O)O))O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Purine 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
  • Primary aromatic amine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Oxolane
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary alcohol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Polyol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Amine
  • Primary alcohol
  • Primary amine
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.84 mg/mLALOGPS
logP-1.8ALOGPS
logP-7.4ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)5ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area311.75 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity117.09 m3·mol-1ChemAxon
Polarizability48.69 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0910520000-894488255e0d2059a6caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-af7d8977d3d229ea73eeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-39c6318a5ada8cb3ebb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001r-1901470000-134113735239a2586876View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1901000000-48fb3c4c1d3e3f084d3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0563-3900000000-f9f285dafe2da95e8009View in MoNA
References
References:
  • 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. [22200665 ]
  • 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. [20739303 ]
  • 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. [23064409 ]
  • 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. [21063061 ]
  • 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. [23292602 ]
  • 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. [16530732 ]
  • 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. [19608713 ]
  • 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. [17321523 ]
  • 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. [19505928 ]
  • 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. [21150257 ]
  • 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. [16434435 ]
  • 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. [21115809 ]
  • 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. [16323274 ]
  • 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. [19208694 ]
  • 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. [17163903 ]
  • 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. [17719035 ]
  • 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. [18476862 ]
  • 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. [16551270 ]
  • 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. [17719034 ]
Synthesis Reference: 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
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CAS2140-58-1
ChEBI57498
HMDBHMDB06557
IAF126035161
KEGGC00498
MetaboLightsMTBLC57498
PubChem25244286