Alpha-D-Glucose (CHEM022792)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:53:29 UTC
Update Date2016-11-09 01:17:34 UTC
Accession NumberCHEM022792
Identification
Common NameAlpha-D-Glucose
ClassSmall Molecule
DescriptionD-Glucopyranose having alpha-configuration at the anomeric centre.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
alpha-D-GLCChEBI
alpha-DextroseChEBI
a-D-GLCGenerator
Α-D-GLCGenerator
a-DextroseGenerator
Α-dextroseGenerator
a-D-GlucoseGenerator
Α-D-glucoseGenerator
a-D-GlucopyranoseHMDB
a-GlucoseHMDB
alpha-D-GlucopyranoseHMDB
alpha-delta-GlucopyranoseHMDB
alpha-delta-GlucoseHMDB
alpha-GlucoseHMDB
HexopyranoseHMDB
Anhydrous dextroseHMDB
D GlucoseHMDB
D-GlucoseHMDB
DextroseHMDB
Dextrose, anhydrousHMDB
GlucoseHMDB
Glucose monohydrateHMDB
Glucose, (DL)-isomerHMDB
Glucose, (L)-isomerHMDB
Glucose, (alpha-D)-isomerHMDB
Glucose, (beta-D)-isomerHMDB
L GlucoseHMDB
L-GlucoseHMDB
Monohydrate, glucoseHMDB
1,3-alpha-D-GlucanHMDB
alpha-1,3-GlucanHMDB
alpha-D-GlucopyranosideHMDB
Chemical FormulaC6H12O6
Average Molecular Mass180.156 g/mol
Monoisotopic Mass180.063 g/mol
CAS Registry Number492-62-6
IUPAC Name(2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameα-glucose
SMILESOC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1
InChI KeyWQZGKKKJIJFFOK-DVKNGEFBSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic 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 Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.09 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9100000000-57ee067515dbaeec1e27Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-311a61760b7c0dc3a7e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-f2beec08615d57ac1a02Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-0ab9-9100000000-eb694004566014e0b267Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9000000000-906b2fd231873b000e08Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-3cd19dc7a445df26b86dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-53278ff57ca00e1b5d1aSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9000000000-c4182c64988208ac78b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-a4ec4f0b1e29e360a952Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-6900000000-7b3ea9c64ecc8d4ac867Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-ec2bf4918640a0a36398Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2900000000-2448926b508622464fe7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-8900000000-4c073cb93b78120113e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-ece70093ab5d3c331ac4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-b0bc47623e7b2ca31c02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-3900000000-648e1637af29cf2a3518Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9200000000-9e6f46a1cbf52d6e347aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01qa-0900000000-04ceb34d441ff6a75763Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dl-9400000000-a8f1ceab155611f949c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ow-9000000000-358f68fc2b7a72c27546Spectrum
1D NMR1H 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
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D 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 IDNot Available
HMDB IDHMDB0003345
FooDB IDFDB011829
Phenol Explorer IDNot Available
KNApSAcK IDC00001122
BiGG IDNot Available
BioCyc IDALPHA-GLUCOSE
METLIN ID6897
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID71358
ChEBI ID17925
PubChem Compound ID79025
Kegg Compound IDC00267
YMDB IDYMDB00273
ECMDB IDECMDB03345
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19443021
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=25568069
3. Simmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp.
4. Simmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp.
5. Onyshchenko AM, Korobkova KS, Kovalenko NK, Kasumova SO, Skrypal' IH: [The role of the carbohydrate composition of the glycocalyx in some species of lactobacilli in the manifestation of their adhesive properties]. Mikrobiol Z. 1999 Nov-Dec;61(6):22-8.
6. Georgiou S, Pasmatzi E, Monastirli A, Sakkis T, Alachioti S, Tsambaos D: Age-related alterations in the carbohydrate residue composition of the cell surface in the unexposed normal human epidermis. Gerontology. 2005 May-Jun;51(3):155-60.
7. Skrypal' IH, Tokovenko IP, Malynovs'ka LP: [Carbohydrate receptors for Mycoplasma fermentans adhesion on human epithelial tissues]. Mikrobiol Z. 1995 Jul-Aug;57(4):17-22.
8. Dalmau SR, Freitas CS: Sugar inhibition of the lectin jacalin: comparison of three assays. Braz J Med Biol Res. 1989;22(5):601-10.
9. Van Cleve JW: Improved preparation of methyl 4,6-O-benzylidene-alpha-d-glucopyranoside. Carbohydr Res. 1971 Apr;17(2):461-4.
10. Yariv J, Kalb AJ, Levitzki A: The interaction of concanavalin A with methyl alpha-D-glucopyranoside. Biochim Biophys Acta. 1968 Sep 3;165(2):303-5.
11. Binder TP, Robyt JF: p-Nitrophenyl alpha-D-glucopyranoside, a new substrate for glucansucrases. Carbohydr Res. 1983 Dec 23;124(2):287-99.
12. Farnback M, Eriksson L, Widmalm G: Methyl 3-O-beta-L-fucopyranosyl alpha-D-glucopyranoside trihydrate. Acta Crystallogr C. 2003 Mar;59(Pt 3):o171-3. Epub 2003 Feb 28.
13. Pan Q, Noll BC, Serianni AS: Methyl 4-O-beta-D-galactopyranosyl alpha-D-glucopyranoside (methyl alpha-lactoside). Acta Crystallogr C. 2005 Dec;61(Pt 12):o674-7. Epub 2005 Nov 11.
14. Christiane Godl, Thornthan Sawangwan, Bernd Nidetzky, Mario Muller, 'Method For Producing 2-O-Glyceryl-Alpha-D-Glucopyranoside.' U.S. Patent US20090318372, issued December 24, 2009.: http://www.google.ca/patents/US20090318372
15. Wan S. Kim, Seo Y. Jeong, James C. McRea, 'Amido-phenyl-.alpha.-D-glucopyranoside derivatives.' U.S. Patent US4536572, issued August, 1983.: http://www.google.ca/patents/US4536572
16. Shoji Usami, Kohtaro Kirimura, Hiroyuki Nakagawa, Yukio Dobashi, Masaaki Yoshiyama, Susumu Shimura, Yoshio Ito, 'Method of producing 1-menthyl- .alpha.-D-glucopyranoside.' U.S. Patent US6277602, issued September, 1996.: http://www.google.ca/patents/US6277602