NP-MRD: Showing NP-Card for Methyl beta-D-glucopyranoside (NP0086503)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-05-11 16:22:36 UTC

Updated at

2022-05-11 16:22:36 UTC

NP-MRD ID

NP0086503

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methyl beta-D-glucopyranoside

Description

Methyl beta-D-glucopyranoside, also known as methylmannoside or methylglucoside, 13C-labeled, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Methyl beta-D-glucopyranoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methyl beta-D-glucopyranoside has been detected, but not quantified in, cereals and cereal products and milk (cow). Methyl beta-D-glucopyranoside is found in Ahnfeltia plicata, Cichorium intybus, Euterpe precatoria, Paxillus involutus, Perilla frutescens, Phlomoides tuberosa, Pseudoceratina purpurea, Quassia amara and Rosa laevigata. This could make methyl beta-D-glucopyranoside a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2    3    8                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    9                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6   12   13                                                  
CONECT    8    2                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
CONECT   11    6                                                            
CONECT   12    1    7                                                       
CONECT   13    3    7                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
Methyl b-D-glucopyranoside	Generator
Methyl β-D-glucopyranoside	Generator
Methyl D-glucopyranoside	MeSH
Methylglucoside, 13C-labeled	MeSH
Methyl-alpha-D-mannoside	MeSH
alpha-Methylglucoside	MeSH
Methyl-alpha-D-glucoside	MeSH
Methylglucoside, 2H-labeled, (beta-D)-isomer	MeSH
alpha-Methylmannose	MeSH
Methylglucoside, (alpha-D)-isomer	MeSH
Methylmannoside	MeSH
Methylglucoside, (beta-D)-isomer	MeSH
Methyl alpha-D-mannopyranoside	MeSH
alpha-Methylmannoside	MeSH
Methyl mannoside, (alpha-D)-isomer	MeSH
Methyl D-glucoside	MeSH
Methyl alpha-D-glucopyranoside	MeSH
Methylglucoside, 5-(17)O-labeled	MeSH
Methylglucoside, 13C-labeled, (beta-D)-isomer	MeSH
beta-Methyl-D-glucoside	MeSH
alpha-Methyl-D-glucopyranoside	MeSH
Methyl-D-glucoside	MeSH
1-O-Methylglucose	MeSH
alpha-Methyl-D-mannose	MeSH
beta-Methylglucoside	MeSH
Methyl glucose	MeSH
AlphaMG	MeSH
Methylglucoside, 6-(13)C-labeled	MeSH
Methyl beta-D-mannopyranoside	MeSH
beta-Methylmannoside	MeSH
Methyl D-mannopyranoside	MeSH
Methylmannoside, alpha-D-isomer	MeSH
Methyl-alpha-glucopyranoside	MeSH
alpha-Methyl-D-glucoside	MeSH
Methylmannose	MeSH
Methyl alpha-D-glucoside	MeSH
Methyl mannoside	MeSH
Methylglucoside, 6-(17)O-labeled, (alpha-L)-isomer	MeSH
D-Glucoside, methyl	MeSH
alpha-Methylglucose	MeSH
Methylglucoside	MeSH
1-O-Methyl-alpha-D-mannose	HMDB
1-O-Methyl-beta -D-glucopyranoside	HMDB
1-O-Methyl-beta-D-glucopyranoside	HMDB
2-(Hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol	HMDB
alpha-Methyl-D -mannoside	HMDB
alpha-Methyl-D-galactoside	HMDB
alpha-Methyl-D-mannoside	HMDB
beta -D-Glucopyranoside, methyl	HMDB
beta -D-Methylglucopyranoside	HMDB
beta -Methylglucoside	HMDB
beta-D-Glucopyranoside, methyl	HMDB
beta-Methyl-D-galactoside	HMDB
Methyl beta -D-glucopyranoside	HMDB
Methyl beta -D-glucoside	HMDB
Methyl beta-D-galactoside	HMDB
Methyl beta-D-glucoside	HMDB
Methyl galactoside	HMDB
Methyl hexopyranoside	HMDB
Methyl-alpha-D -glucopyranoside	HMDB
Methyl-alpha-D-mannopyranoside	HMDB
Methyl-beta-D-galacto-pyranoside	HMDB
Methyl-beta-galactose	HMDB
Methylgalactoside	HMDB
O1-Methyl-mannose	HMDB

Chemical Formula

C₇H₁₄O₆

Average Mass

194.1825 Da

Monoisotopic Mass

194.07904 Da

IUPAC Name

2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol

Traditional Name

methyl-α-D-mannoside

CAS Registry Number

Not Available

SMILES

COC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3

InChI Key

HOVAGTYPODGVJG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ahnfeltia plicata	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Cichorium intybus	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Euterpe precatoria	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Paxillus involutus	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phlomoides tuberosa	LOTUS Database	35616633
Pseudoceratina purpurea	LOTUS Database	35616633
Quassia amara	LOTUS Database	35616633
Rosa laevigata	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

O-glycosyl compound
Oxane
Monosaccharide
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Acetal
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

a β-D-galactoside (METHYL-BETA-D-GALACTOSIDE )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-2.5	ALOGPS
logP	-2.3	ChemAxon
logS	0.65	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	99.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	40.67 m³·mol⁻¹	ChemAxon
Polarizability	18.37 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

External Links

HMDB ID

HMDB0029965

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001246

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2108

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methyl beta-D-glucopyranoside (NP0086503)

MOL for NP0086503 (Methyl beta-D-glucopyranoside)

3D MOL for NP0086503 (Methyl beta-D-glucopyranoside)

3D SDF for NP0086503 (Methyl beta-D-glucopyranoside)

3D-SDF for NP0086503 (Methyl beta-D-glucopyranoside)

PDB for NP0086503 (Methyl beta-D-glucopyranoside)

3D PDB for NP0086503 (Methyl beta-D-glucopyranoside)

SMILES for NP0086503 (Methyl beta-D-glucopyranoside)

INCHI for NP0086503 (Methyl beta-D-glucopyranoside)

Structure for NP0086503 (Methyl beta-D-glucopyranoside)

3D Structure for NP0086503 (Methyl beta-D-glucopyranoside)