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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:33:51 UTC
Update Date2019-07-23 06:05:17 UTC
HMDB IDHMDB0029965
Secondary Accession Numbers
  • HMDB29965
Metabolite Identification
Common NameMethyl beta-D-glucopyranoside
DescriptionMethyl beta-D-glucopyranoside, also known as Beta-methyl-D-glucoside or methyl hexopyranoside, 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).
Structure
Data?1563861917
Synonyms
ValueSource
1-O-Methyl-beta-D-glucopyranosideChEBI
beta-D-MethylglucopyranosideChEBI
Beta-Methyl-D-glucosideChEBI
beta-MethylglucosideChEBI
Methyl beta-D-glucosideChEBI
Methyl hexopyranosideChEBI
1-O-Methyl-b-D-glucopyranosideGenerator
1-O-Methyl-β-D-glucopyranosideGenerator
b-D-MethylglucopyranosideGenerator
Β-D-methylglucopyranosideGenerator
b-Methyl-D-glucosideGenerator
Β-methyl-D-glucosideGenerator
b-MethylglucosideGenerator
Β-methylglucosideGenerator
Methyl b-D-glucosideGenerator
Methyl β-D-glucosideGenerator
Methyl b-D-glucopyranosideGenerator
Methyl β-D-glucopyranosideGenerator
Methyl D-glucopyranosideHMDB
Methyl D-glucosideHMDB
MethylglucosideHMDB
Methylglucoside, (beta-D)-isomerHMDB
1-O-MethylglucoseHMDB
D-Glucoside, methylHMDB
Methyl glucoseHMDB
Methyl-D-glucosideHMDB
Chemical FormulaC7H14O6
Average Molecular Weight194.1825
Monoisotopic Molecular Weight194.07903818
IUPAC Name(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
Traditional Namemethyl β-d-glucoside
CAS Registry Number709-50-2
SMILES
CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
InChI Identifier
InChI=1S/C7H14O6/c1-12-7-6(11)5(10)4(9)3(2-8)13-7/h3-11H,2H2,1H3/t3-,4-,5+,6-,7-/m1/s1
InChI KeyHOVAGTYPODGVJG-XUUWZHRGSA-N
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point108 - 110 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility862 g/LALOGPS
logP-2.5ALOGPS
logP-2.3ChemAxon
logS0.65ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area99.38 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity40.67 m³·mol⁻¹ChemAxon
Polarizability18.3 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kdi-8900000000-92619c7d67bf338cb44aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-80684999a3f416746a4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004j-3900000000-1032edc90a7c53a1f1dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0btd-9200000000-f1822159831fae8d9a02Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2900000000-28d99d64c5ca71550794Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01xx-5900000000-2f963b33d61cd4e807bcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0596-9100000000-5d4f1d49bbc77216c482Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01642
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound445238
PDB IDNot Available
ChEBI ID320055
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in binding
Specific function:
Calcium-dependent lectin involved in innate immune defense. Binds mannose, fucose and N-acetylglucosamine on different microorganisms and activates the lectin complement pathway. Binds to late apoptotic cells, as well as to apoptotic blebs and to necrotic cells, but not to early apoptotic cells, facilitating their uptake by macrophages. May bind DNA
Gene Name:
MBL2
Uniprot ID:
P11226
Molecular weight:
26143.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]