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beta-D-Glucopyranose (FDB011824)

Record Information
Version1.0
Creation date2010-04-08 22:09:51 UTC
Update date2020-09-17 15:31:48 UTC
Primary IDFDB011824
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namebeta-D-Glucopyranose
Descriptionbeta-D-Glucopyranose is one of the four cyclic isomers of D-glucose. Glucose (CAS: 50-99-7) is a monosaccharide containing six carbon atoms and an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is the most abundant monosaccharide, a subcategory of carbohydrates and it is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight. In plants and algae, it is used to make cellulose in cell walls, which is the most abundant carbohydrate polymer found in nature. Glucose is 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. In animals, glucose arises from the breakdown of glycogen in a process known as glycogenolysis. Glucose is synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol, by a process known as gluconeogenesis. D-Glucose is found to be associated with 3-methyl-crotonyl-glycinuria, growth hormone deficiency, and primary hypomagnesemia, which are inborn errors of metabolism. Glucose is used therapeutically in fluid and nutrient replacement.
CAS Number492-61-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
Not AvailableNot 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
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d69092015-03-01View Spectrum
GC-MSbeta-D-Glucopyranose, non-derivatized, GC-MS Spectrumsplash10-00di-9721000000-6ca4df9ac892160d11c5Spectrum
GC-MSbeta-D-Glucopyranose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-fff85ff382393ec04a54Spectrum
GC-MSbeta-D-Glucopyranose, non-derivatized, GC-MS Spectrumsplash10-00di-9721000000-6ca4df9ac892160d11c5Spectrum
GC-MSbeta-D-Glucopyranose, non-derivatized, GC-MS Spectrumsplash10-00di-9621000000-fff85ff382393ec04a54Spectrum
Predicted GC-MSbeta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bSpectrum
Predicted GC-MSbeta-D-Glucopyranose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bSpectrum
Predicted GC-MSbeta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_3_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSbeta-D-Glucopyranose, TMS_3_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-0002-9300000000-839f41cf94a071fcdb372020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0002-9000000000-807f75d14f3d0b66f5bd2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-000t-9000000000-b89668f86992a83636642020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-7900000000-9a673c2e4b82ca3974212020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0a4r-9100000000-b70415588e768ddce5ef2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9000000000-73dc84dd88d8ae69fe022020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0a4i-9000000000-ba39d4ed9431a1d01eab2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a4i-9000000000-a61efd1469735758b3172020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-7900000000-9a673c2e4b82ca3974212020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4r-9100000000-9c25b149885d8a48aab52020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-76d92ea96364c24ecfb02020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-ba39d4ed9431a1d01eab2020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-9000000000-a61efd1469735758b3172020-03-26View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 1V, positivesplash10-03di-0900000000-c44bda60a6fcba163df32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 2V, positivesplash10-03di-0900000000-2d4fcc06b5f1a548e0ac2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 3V, positivesplash10-03dj-1900000000-d66ef20973a9aed890d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 4V, positivesplash10-01ot-2900000000-f15e86af30f3065466a82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 5V, positivesplash10-000b-4900000000-2a9008fcc11325c7a3fe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 6V, positivesplash10-000b-7900000000-afd4ac776eb4bedb6bff2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 7V, positivesplash10-000j-9700000000-394bb6f6163ff53c203a2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 8V, positivesplash10-000i-9400000000-afcfe7141c6578d962062020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 9V, positivesplash10-000i-9300000000-011aa587ff83208ceaa62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 10V, positivesplash10-000i-9200000000-8d13450ee922cef5d1732020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 11V, positivesplash10-000i-9200000000-ba587aac166359ffc7d52020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QqQ 12V, positivesplash10-000i-9100000000-e62915efe3ed02f208b62020-07-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
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).