AFCDB: D-Glucose (FDB012530)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:13 UTC

Update date

2023-02-22 17:29:04 UTC

Primary ID

FDB012530

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

D-Glucose

Description

Glucose 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 Number

492-61-5

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	782 g/L	ALOGPS
logP	-2.6	ALOGPS
logP	-2.9	ChemAxon
logS	0.64	ALOGPS
pKa (Strongest Acidic)	11.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	35.92 m³·mol⁻¹	ChemAxon
Polarizability	16.35 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C6H12O6

IUPAC name

(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

InChI Identifier

InChI=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 Key

WQZGKKKJIJFFOK-VFUOTHLCSA-N

Isomeric SMILES

OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Oxane
Secondary alcohol
Hemiacetal
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucopyranose (CHEBI:15903 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	146-150 oC
Boiling Point	Not Available
Experimental Water Solubility	1200 mg/mL at 30 oC	MULLIN,JW (1972)
Experimental logP	-3.24	SANGSTER (1994)
Experimental pKa	pKa1 12.34 (25°)	DFC
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-a60df7b043f8947d6909	2015-03-01	View Spectrum
GC-MS	beta-D-Glucopyranose, non-derivatized, GC-MS Spectrum	splash10-00di-9721000000-6ca4df9ac892160d11c5	Spectrum
GC-MS	beta-D-Glucopyranose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-fff85ff382393ec04a54	Spectrum
GC-MS	beta-D-Glucopyranose, non-derivatized, GC-MS Spectrum	splash10-00di-9721000000-6ca4df9ac892160d11c5	Spectrum
GC-MS	beta-D-Glucopyranose, non-derivatized, GC-MS Spectrum	splash10-00di-9621000000-fff85ff382393ec04a54	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_3_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	beta-D-Glucopyranose, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0002-9300000000-839f41cf94a071fcdb37	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0002-9000000000-807f75d14f3d0b66f5bd	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000t-9000000000-b89668f86992a8363664	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-7900000000-9a673c2e4b82ca397421	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9100000000-b70415588e768ddce5ef	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-73dc84dd88d8ae69fe02	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-a61efd1469735758b317	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-7900000000-9a673c2e4b82ca397421	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9100000000-9c25b149885d8a48aab5	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-76d92ea96364c24ecfb0	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a61efd1469735758b317	2020-03-26	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-03di-0900000000-c44bda60a6fcba163df3	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-03di-0900000000-2d4fcc06b5f1a548e0ac	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-03dj-1900000000-d66ef20973a9aed890d5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-01ot-2900000000-f15e86af30f3065466a8	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-000b-4900000000-2a9008fcc11325c7a3fe	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-000b-7900000000-afd4ac776eb4bedb6bff	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-000j-9700000000-394bb6f6163ff53c203a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-000i-9400000000-afcfe7141c6578d96206	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000i-9300000000-011aa587ff83208ceaa6	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000i-9200000000-8d13450ee922cef5d173	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 11V, positive	splash10-000i-9200000000-ba587aac166359ffc7d5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-000i-9100000000-e62915efe3ed02f208b6	2020-07-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17634

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00122

CRC / DFC (Dictionary of Food Compounds) ID

EAFUS ID

Dr. Duke ID

BIGG ID

KNApSAcK ID

Not Available

HET ID

1A47

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Glucose

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
sweetener	50505	Substance that sweeten food, beverages, medications, etc.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Alpha-galactosidase A	GLA	P06280
Lactase-phlorizin hydrolase	LCT	P09848
Trehalase	TREH	O43280
Glycogen debranching enzyme	AGL	P35573
Sucrase-isomaltase, intestinal	SI	P14410
Lysosomal alpha-glucosidase	GAA	P10253
Maltase-glucoamylase, intestinal	MGAM	O43451
Neutral alpha-glucosidase C	GANC	Q8TET4
Alpha-lactalbumin	LALBA	P00709
Glucosylceramidase	GBA	P04062
Glucokinase	GCK	P35557
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789
Hexokinase-1	HK1	P19367
Non-lysosomal glucosylceramidase	GBA2	Q9HCG7
Glucokinase regulatory protein	GCKR	Q14397
Glucose-6-phosphatase	G6PC	P35575
Glucose-6-phosphatase 2	G6PC2	Q9NQR9
Neutral alpha-glucosidase AB	GANAB	Q14697
Glucose-6-phosphate isomerase	GPI	P06744
Solute carrier family 2, facilitated glucose transporter member 1	SLC2A1	P11166
Glucose-6-phosphatase 3	G6PC3	Q9BUM1

Pathways

Name	SMPDB Link	KEGG Link
Galactose Metabolism	SMP00043	map00052
Gluconeogenesis	SMP00128	map00010
Glucose-Alanine Cycle	SMP00127	Not Available
Glycolysis	SMP00040	map00010
Lactose Degradation	SMP00457	Not Available
Lactose Synthesis	SMP00444	Not Available
Transfer of Acetyl Groups into Mitochondria	SMP00466	Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not 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).

D-Glucose (FDB012530)

Structure for FDB012530 (D-Glucose)