Showing Compound beta-D-Glucopyranose (FDB011824)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:51 UTC

Update date

2020-09-17 15:31:48 UTC

Primary ID

FDB011824

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

beta-D-Glucopyranose

Description

beta-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 Number

492-61-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Glucose	ChEMBL, HMDB
b-D-Glucose	Generator
β-D-glucose	Generator
b-D-Glucopyranose	HMDB, Generator
b-Dextrose	HMDB
b-Glucose	HMDB
beta-D-Glucopyranose	HMDB, KEGG
beta-Dextrose	HMDB
beta-Glucose	HMDB
D Glucose	MeSH, HMDB
Glucose, (beta-D)-isomer	MeSH, HMDB
Dextrose	MeSH, HMDB
Glucose, (DL)-isomer	MeSH, HMDB
D-Glucose	MeSH, HMDB
D-Glucopyranose	HMDB
D-Glucopyranoside	HMDB
beta-D-Glucopyranoside	HMDB
beta-D-Glucose	HMDB
β-D-Glucopyranose	HMDB
β-D-Glucopyranoside	HMDB
β-D-Glucose	HMDB
β-Dextrose	HMDB
β-Glucose	HMDB
D-GLC	HMDB
D-GLCP	HMDB
GLC-OH	HMDB
β-d-glucopyranose	biospider
B-d-glucopyranose	biospider
Beta-d-glucopyranose	biospider
beta-D-glucose	manual
beta-delta-Glucopyranose	HMDB

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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Subcellular:

Cytoplasm

Biofluid and excreta:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	Mp 148-150° (anhyd.)	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	-3.24	SANGSTER (1994)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +17.5 -> +52.5 (c, 10 in H2O)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9721000000-6ca4df9ac892160d11c5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-fff85ff382393ec04a54	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9721000000-6ca4df9ac892160d11c5	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-fff85ff382393ec04a54	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0002-9300000000-839f41cf94a071fcdb37	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0002-9000000000-807f75d14f3d0b66f5bd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000t-9000000000-b89668f86992a8363664	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-7900000000-9a673c2e4b82ca397421	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9100000000-b70415588e768ddce5ef	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-73dc84dd88d8ae69fe02	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-a61efd1469735758b317	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-7900000000-9a673c2e4b82ca397421	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9100000000-9c25b149885d8a48aab5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-76d92ea96364c24ecfb0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a61efd1469735758b317	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-03di-0900000000-c44bda60a6fcba163df3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-03di-0900000000-2d4fcc06b5f1a548e0ac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-03dj-1900000000-d66ef20973a9aed890d5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-01ot-2900000000-f15e86af30f3065466a8	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-000b-4900000000-2a9008fcc11325c7a3fe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-000b-7900000000-afd4ac776eb4bedb6bff	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-ecd0aedc67c9a2eec60f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-2900000000-e4daf22c7320ccc41812	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9200000000-91fc3940732f782a88bb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-1900000000-e9f3e728d1b340759a09	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-5900000000-c0a478f2b9c5bbc6c4ba	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-06852e2088bf1c6b38c4	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-a60df7b043f8947d6909	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

15903

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00516

CRC / DFC (Dictionary of Food Compounds) ID

HHS40-R:GZP89-I

EAFUS ID

Not Available

Dr. Duke ID

BETA-GLUCOSE|D-GLUCOSE|GLUCOSE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

BGC

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
acetylcholinergic	38323	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 edemic			DUKE
anti hepatotoxic	62868	Any compound that is able to prevent damage to the liver.	DUKE
anti ketotic			DUKE
anti secretory			DUKE
anti varicose	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
hyperglycemic	76916	A drug which increases the blood glucose level.	DUKE
memory enhancer	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE

Enzymes

Name	Gene Name	UniProt ID
Lactase-phlorizin hydrolase	LCT	P09848
Beta-galactosidase	GLB1	P16278
Trehalase	TREH	O43280
Maltase-glucoamylase, intestinal	MGAM	O43451
Glucosylceramidase	GBA	P04062
Glucokinase	GCK	P35557
Hexokinase-3	HK3	P52790
Hexokinase-2	HK2	P52789
Hexokinase-1	HK1	P19367
Glucokinase regulatory protein	GCKR	Q14397
Aldose 1-epimerase	GALM	Q96C23

Pathways

Name	SMPDB Link	KEGG Link
Gluconeogenesis	SMP00128	map00010
Glycolysis	SMP00040	map00010
Trehalose Degradation	SMP00467	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

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

Showing Compound beta-D-Glucopyranose (FDB011824)

Structure for FDB011824 (beta-D-Glucopyranose)