Record Information
Version1.0
Creation date2010-04-08 22:09:51 UTC
Update date2019-11-27 17:19:08 UTC
Primary IDFDB011824
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-D-Glucopyranose
DescriptionA glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. This group contains a benzene and also an ethylene group, being derived from styrolene. Coniferin, C16H22O8, occurs in the cambium of conifer wood. Emulsin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emulsin glucose and vanillin. Syringin, which occurs in the bark of Syringe vulgaris, is a methoxyconiferin. Phloridzus occurs in the root-bark of various fruit trees; it hydrolyses to glucose and phloretin, which is the phloroglucin ester of paraoxyhydratropic acid. It is related to the pentosides naringin, C21HEOi1, which hydrolyses to rhamnose and naringenin, the phioroglucin ester of para-oxycinnamic acid, and hesperidin, which hydrolyses to rhamnose and hesperetin, the phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferulic acid, C10H10O4. A primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. Classification of the glucosides is a matter of some difficulty. One based on the chemical constitution of the non-glucose part of the molecules has been proposed that frames four groups: (I) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, (4) anthracene derivatives. A group may also be made to include the cyanogenetic glucosides, i.e. those containing prussic acid. Other classifications follow a botanical classification, which has several advantages; in particular, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed here. [HMDB].
CAS Number492-61-5
Structure
Thumb
Synonyms
SynonymSource
beta-D-GlucopyranoseKegg
b-D-GlucopyranoseGenerator
b-D-GlucoseGenerator
Β-D-glucoseGenerator
GlucoseHMDB
b-DextroseHMDB
b-GlucoseHMDB
beta-delta-GlucopyranoseHMDB
beta-DextroseHMDB
beta-GlucoseHMDB
D GlucoseHMDB
Glucose, (beta-D)-isomerHMDB
DextroseHMDB
Monohydrate, glucoseHMDB
Anhydrous dextroseHMDB
Glucose, (DL)-isomerHMDB
Glucose, (alpha-D)-isomerHMDB
D-GlucoseHMDB
Dextrose, anhydrousHMDB
Glucose monohydrateHMDB
D-GlucopyranoseHMDB
D-GlucopyranosideHMDB
beta-D-GlucopyranosideHMDB
beta-D-GlucoseHMDB
β-D-GlucopyranosideHMDB
β-DextroseHMDB
β-GlucoseHMDB
β-d-glucopyranosebiospider
B-d-glucopyranosebiospider
Beta-d-glucopyranosebiospider
beta-D-glucosemanual
β-D-glucoseGenerator
Predicted Properties
PropertyValueSource
logP-2.9ChemAxon
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
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H12O6
IUPAC name(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
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-VFUOTHLCSA-N
Isomeric SMILESOC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
Melting PointMp 148-150° (anhyd.)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logP-3.24SANGSTER (1994)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +17.5 -> +52.5 (c, 10 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9721000000-6ca4df9ac892160d11c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-fff85ff382393ec04a54View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9721000000-6ca4df9ac892160d11c5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-fff85ff382393ec04a54View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d6909View in MoNA
ChemSpider ID58238
ChEMBL IDCHEMBL1614854
KEGG Compound IDC00221
Pubchem Compound ID64689
Pubchem Substance IDNot Available
ChEBI ID15903
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00516
CRC / DFC (Dictionary of Food Compounds) IDHHS40-R:GZP89-I
EAFUS IDNot Available
Dr. Duke IDBETA-GLUCOSE|D-GLUCOSE|GLUCOSE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDBGC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlucose
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
acetylcholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
anti edemicDUKE
anti hepatotoxic62868 Any compound that is able to prevent damage to the liver.DUKE
anti ketoticDUKE
anti secretoryDUKE
anti varicose52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
hyperglycemic76916 A drug which increases the blood glucose level.DUKE
memory enhancer52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
Enzymes
NameGene NameUniProt ID
Lactase-phlorizin hydrolaseLCTP09848
Beta-galactosidaseGLB1P16278
TrehalaseTREHO43280
Maltase-glucoamylase, intestinalMGAMO43451
GlucosylceramidaseGBAP04062
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
Glucokinase regulatory proteinGCKRQ14397
Aldose 1-epimeraseGALMQ96C23
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128 map00010
GlycolysisSMP00040 map00010
Trehalose DegradationSMP00467 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).