Bovine Metabolome Database: Showing metabocard for Beta-D-Glucose (BMDB0000516)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:31:59 UTC

Update Date

2020-06-04 20:32:36 UTC

BMDB ID

BMDB0000516

Secondary Accession Numbers

BMDB00516

Metabolite Identification

Common Name

Beta-D-Glucose

Description

D-Glucose, also known as b-D-glucopyranose, 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. D-Glucose exists in all living species, ranging from bacteria to plants to humans. D-Glucose, with regard to humans, has been found to be associated with several diseases such as 3-hydroxyacyl-coa dehydrogenase deficiency, short-chain l-3-hydroxyacyl-coa dehydrogenase deficiency, and colorectal cancer; D-glucose has also been linked to several inborn metabolic disorders including primary hypomagnesemia and 21-hydroxylase deficiency. Based on a literature review a significant number of articles have been published on D-Glucose.

Structure

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

Synonyms

Value	Source
WURCS=2.0/1,1,0/[a2122h-1b_1-5]/1/	ChEBI
beta-D-Glucopyranose	Kegg
b-D-Glucopyranose	Generator
Glucose	ChEMBL, HMDB
b-D-Glucose	Generator
β-D-glucose	Generator
b-Dextrose	HMDB
b-Glucose	HMDB
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-Glucopyranoside	HMDB
β-D-Glucose	HMDB
β-Dextrose	HMDB
β-Glucose	HMDB
D-GLC	HMDB
D-GLCP	HMDB
GLC-OH	HMDB

Chemical Formula

C₆H₁₂O₆

Average Molecular Weight

180.1559

Monoisotopic Molecular Weight

180.063388116

IUPAC Name

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

Traditional Name

glucoside

CAS Registry Number

492-61-5

SMILES

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

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

Chemical Taxonomy

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

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.24	SANGSTER (1994)

Predicted Properties

Property	Value	Source
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

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9721000000-6ca4df9ac892160d11c5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-fff85ff382393ec04a54	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9721000000-6ca4df9ac892160d11c5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-9621000000-fff85ff382393ec04a54	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0np0-9700000000-e8d638dc817e46b97d7b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive	splash10-004i-6122690000-eaf6f7adf34ccd0c667b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0002-9300000000-839f41cf94a071fcdb37	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0002-9000000000-807f75d14f3d0b66f5bd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-000t-9000000000-b89668f86992a8363664	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-000i-7900000000-9a673c2e4b82ca397421	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0a4r-9100000000-b70415588e768ddce5ef	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0a4i-9000000000-73dc84dd88d8ae69fe02	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0a4i-9000000000-a61efd1469735758b317	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-000i-7900000000-9a673c2e4b82ca397421	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4r-9100000000-9c25b149885d8a48aab5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-76d92ea96364c24ecfb0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-ba39d4ed9431a1d01eab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0a4i-9000000000-a61efd1469735758b317	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, positive	splash10-03di-0900000000-c44bda60a6fcba163df3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 2V, positive	splash10-03di-0900000000-2d4fcc06b5f1a548e0ac	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 3V, positive	splash10-03dj-1900000000-d66ef20973a9aed890d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, positive	splash10-01ot-2900000000-f15e86af30f3065466a8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 5V, positive	splash10-000b-4900000000-2a9008fcc11325c7a3fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 6V, positive	splash10-000b-7900000000-afd4ac776eb4bedb6bff	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 7V, positive	splash10-000j-9700000000-394bb6f6163ff53c203a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, positive	splash10-000i-9400000000-afcfe7141c6578d96206	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 9V, positive	splash10-000i-9300000000-011aa587ff83208ceaa6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 10V, positive	splash10-000i-9200000000-8d13450ee922cef5d173	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 11V, positive	splash10-000i-9200000000-ba587aac166359ffc7d5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - QqQ 12V, positive	splash10-000i-9100000000-e62915efe3ed02f208b6	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-a60df7b043f8947d6909	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Blood
Brain
Colostrum
Eye Lens
Fibroblasts
Intestine
Kidney
Liver
Lung
Muscle
Neuron
Pancreas
Placenta
Prostate Tissue
Ruminal Fluid

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycolysis		Not Available
Gluconeogenesis		Not Available
Trehalose Degradation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Cortex	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Gland	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Adrenal Medulla	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Bladder	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 24440255	details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Colostrum	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Eye Lens	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Fibroblasts	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Intestine	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Kidney	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Lung	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Muscle	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25637742	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Ruminal Fluid	Detected and Quantified	763.813 +/- 751.731 uM	Not Specified	Not Specified	Normal	Fozia Saleem, Sou...	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Ruminal Fluid	Detected and Quantified	2415.813 +/- 1248.434 uM	Not Specified	Not Specified	Rumen acidosis	Fozia Saleem, Sou...	details

External Links

HMDB ID

HMDB0000122

DrugBank ID

DB02379

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Glucose

METLIN ID

Not Available

PubChem Compound

64689

PDB ID

Not Available

ChEBI ID

15903

References

Synthesis Reference

Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim. Production of b-D-glucose. Praxis der Naturwissenschaften, Chemie (1986), 35(4), 23.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Aldose 1-epimerase

General function:: Carbohydrate transport and metabolism
Specific function:: Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose (By similarity).
Gene Name:: GALM
Uniprot ID:: Q5EA79
Molecular weight:: 37614.0

Reactions

Alpha-D-Glucose → Beta-D-Glucose	details

Enzyme Details

2. Hexokinase-1

General function:: Involved in ATP binding
Specific function:: Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:: HK1
Uniprot ID:: P27595
Molecular weight:: 103064.0

Reactions

Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate	details
Beta-D-Glucose + Adenosine triphosphate → Beta-D-Glucose 6-phosphate + ADP	details

Enzyme Details

3. Trehalase

General function:: Not Available
Specific function:: Not Available
Gene Name:: TREH
Uniprot ID:: E1B8N4
Molecular weight:: 65887.0

Reactions

Trehalose + Water → Beta-D-Glucose + Alpha-D-Glucose	details

Showing metabocard for Beta-D-Glucose (BMDB0000516)

Structure for BMDB0000516 (Beta-D-Glucose)

Enzymes

Reactions

Reactions

Reactions