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Showing Compound D-Glucose (FDB012530)

Record Information
Version1.0
Creation date2010-04-08 22:10:13 UTC
Update date2023-02-22 17:29:04 UTC
Primary IDFDB012530
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Glucose
DescriptionGlucose is a monosaccharide containing six carbon atoms and an aldehyde group. It is 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 a primary source of energy for all living organisms. It is a fundamental metabolite found in all organisms, ranging from bacteria to plants to humans. Most of the glucose generated on the Earth is made by plants and algae during photosynthesis from water and carbon dioxide, where it is used to make cellulose (and other polymeric forms of glucose called polysaccharides) that stabilize plant cell walls. Glucose is also found in fruits and other parts of plants in its free state. In animals, glucose can be generated from the breakdown of glycogen in a process known as glycogenolysis. Glucose can also be synthesized de novo in animals. In particular, it can be synthesized in the liver and kidneys from non-carbohydrate intermediates, such as pyruvate and glycerol (and gluconeogenic amino acids such as glycine, serine and alanine), by a process known as gluconeogenesis. Humans also consume large amounts of glucose as part of their regular diet. Ingested glucose initially binds to the receptor for sweet taste on the tongue in humans. This complex of the proteins T1R2 and T1R3 makes it possible to identify glucose-containing food sources. Glucose in the body mainly comes from food - about 300 g per day for the average adult. In humans, the breakdown of glucose-containing polysaccharides happens partly during chewing by means of the enzyme known as amylase, which is contained in saliva, as well as by other enzymes such as maltase, lactase and sucrase on the brush border of the small intestine. The blood sugar content of a healthy person in the short-time fasting state, e.g. after overnight fasting, is about 70 to 100 mg/dL of blood (4 to 5.5 mM). In blood plasma, the measured values are about 10-15% higher. Dysregulated metabolism of glucose can lead to a number of diseases including diabetes. Diabetes is a metabolic disorder where the body is unable to regulate levels of glucose in the blood either because of a lack of insulin in the body or the failure, by cells in the body, to respond properly to insulin. Each of these situations can be caused by persistently high elevations of blood glucose levels (called hyperglycemia), through pancreatic burnout and insulin resistance. Persistently elevated levels of glucose (>6 mM or >120 mg/dL) can lead to the formation of covalent adducts of glucose with plasma proteins through a non-enzymatic process known as glycation. This glycation reaction leads to advanced glycation end products or AGEs (PMID: 24634591 ). AGEs are thought to be the major causes of different diabetic complications. High glucose levels may induce glycation of various structural and functional proteins including plasma proteins and collagen. The non-enzymatic modification of plasma proteins such as albumin, fibrinogen, hemoglobin and globulins may produce various deleterious effects including alteration in drug binding in the plasma, platelet activation, generation of oxygen free radicals, impaired fibrinolysis and impairment in immune system regulation (PMID: 24634591 ). Transiently elevated glucose (up to 7.3 mM or 133 mg/dL) is often seen shortly after the consumption of a meal or a food item that is rich in carbohydrates -- even among very healthy people (PMID: 19885137 ). Glucose is also elevated when an individual is fighting viral or bacterial infections or suffering from traumatic injuries (burns, wounds). In fact, glucose can be significantly elevated (>11 mM or 200 mg/dL) when individuals are experiencing sepsis or septic shock (PMID: 16006275 ). On the other hand, low blood glucose levels (hypoglycemia) where blood glucose is <3.9 mM (70 mg/dL) are common among people with type 1 diabetes and people with type 2 diabetes who take certain diabetic medicines. Certain conditions, such as liver disease, may also cause low levels of blood glucose. Hypoglycemia can lead to fatigue, sleepiness, short temper or feeling faint.
CAS Number492-61-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
GlucoseChEMBL, HMDB
b-D-GlucoseGenerator
β-D-glucoseGenerator
b-D-GlucopyranoseHMDB, Generator
b-DextroseHMDB
b-GlucoseHMDB
beta-D-GlucopyranoseHMDB, KEGG
beta-DextroseHMDB
beta-GlucoseHMDB
D GlucoseMeSH, HMDB
Glucose, (beta-D)-isomerMeSH, HMDB
DextroseMeSH, HMDB
Glucose, (DL)-isomerMeSH, HMDB
D-GlucoseMeSH, HMDB
D-GlucopyranoseHMDB
D-GlucopyranosideHMDB
beta-D-GlucopyranosideHMDB
beta-D-GlucoseHMDB
β-D-GlucopyranoseHMDB
β-D-GlucopyranosideHMDB
β-D-GlucoseHMDB
β-DextroseHMDB
β-GlucoseHMDB
D-GLCHMDB
D-GLCPHMDB
GLC-OHHMDB
(+)-glucosebiospider
Anhydrous dextroseHMDB
CereloseHMDB
Cerelose 2001HMDB
Clearsweet 95HMDB
Clintose LHMDB
Corn sugarHMDB
CPC HydrateHMDB
D-(+)-glucosebiospider
D-GlcChEBI
D-GlcpChEBI
D(+)-glucosebiospider
DextropurHMDB
DextrosolHMDB
GlucodinHMDB
GlucolinHMDB
GoldsugarHMDB
Grape sugarmanual
MeritoseHMDB
Roferose stHMDB
Staleydex 111HMDB
Staleydex 95mHMDB
Tabfine 097(hs)HMDB
VadexHMDB
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 40.00%; H 6.71%; O 53.28%DFC
Melting Point146-150 oC
Boiling PointNot Available
Experimental Water Solubility1200 mg/mL at 30 oCMULLIN,JW (1972)
Experimental logP-3.24SANGSTER (1994)
Experimental pKapKa1 12.34 (25°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
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 ID5589
ChEMBL IDCHEMBL1222250
KEGG Compound IDC00031
Pubchem Compound ID5793
Pubchem Substance IDNot Available
ChEBI ID17634
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00122
CRC / DFC (Dictionary of Food Compounds) IDHHS40-R:HHS42-T
EAFUS ID870
Dr. Duke IDDEXTROSE
BIGG ID33582
KNApSAcK IDNot Available
HET ID1A47
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
sweetener50505 Substance that sweeten food, beverages, medications, etc.DUKE
Enzymes
NameGene NameUniProt ID
Alpha-galactosidase AGLAP06280
Lactase-phlorizin hydrolaseLCTP09848
TrehalaseTREHO43280
Glycogen debranching enzymeAGLP35573
Sucrase-isomaltase, intestinalSIP14410
Lysosomal alpha-glucosidaseGAAP10253
Maltase-glucoamylase, intestinalMGAMO43451
Neutral alpha-glucosidase CGANCQ8TET4
Alpha-lactalbuminLALBAP00709
GlucosylceramidaseGBAP04062
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
Non-lysosomal glucosylceramidaseGBA2Q9HCG7
Glucokinase regulatory proteinGCKRQ14397
Glucose-6-phosphataseG6PCP35575
Glucose-6-phosphatase 2G6PC2Q9NQR9
Neutral alpha-glucosidase ABGANABQ14697
Glucose-6-phosphate isomeraseGPIP06744
Solute carrier family 2, facilitated glucose transporter member 1SLC2A1P11166
Glucose-6-phosphatase 3G6PC3Q9BUM1
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
GluconeogenesisSMP00128 map00010
Glucose-Alanine CycleSMP00127 Not Available
GlycolysisSMP00040 map00010
Lactose DegradationSMP00457 Not Available
Lactose SynthesisSMP00444 Not Available
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).