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 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

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Synonym	Source
b-D-Glucopyranose	Generator
B-d-glucopyranose	biospider
b-D-Glucose	Generator
b-Dextrose	HMDB
b-Glucose	HMDB
beta-D-Glucopyranose	Kegg
Beta-d-glucopyranose	biospider
beta-D-Glucopyranoside	HMDB
beta-D-Glucose	HMDB
beta-D-glucose	manual

Showing 1 to 10 of 31 entries

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

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

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-3.24	SANGSTER (1994)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 40.00%; H 6.71%; O 53.28%	DFC
Melting Point	Mp 148-150° (anhyd.)	DFC
Optical Rotation	[a]20D +17.5 -> +52.5 (c, 10 in H2O)	DFC

Showing 1 to 10 of 14 entries

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

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

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Food	Content Range	Average	Reference

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Biological Effects and Interactions

Health Effects / Bioactivities

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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

Showing 1 to 8 of 8 entries

Enzymes

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