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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2015-03-19 19:45:56 UTC
Update Date2017-12-07 20:19:23 UTC
HMDB IDHMDB0062170
Secondary Accession Numbers
  • HMDB62170
Metabolite Identification
Common NameD-Glucopyranoside
DescriptionD-Glucopyranoside belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
Structure
Thumb
Synonyms
ValueSource
HexoseKegg
D-GalactoseHMDB
GalactopyranoseHMDB
GalactopyranosideHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Named-galactose
CAS Registry NumberNot Available
SMILES
OCC1OC(O)C(O)C(O)C1O
InChI Identifier
InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2
InChI KeyWQZGKKKJIJFFOK-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
logP-2.6ALOGPS
logP-2.9ChemAxon
logS0.64ALOGPS
pKa (Strongest Acidic)11.3ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area110.38 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.3 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08g0-9700000000-d7fbea2263840ca358b3View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-03du-2900000000-8b4969661fc601d4c994View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0229-9000000000-3cd18e57966112492f50View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001128
KNApSAcK IDNot Available
Chemspider ID201
KEGG Compound IDC00738
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound206
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Siewert G, Westphal O: [New synthesis of 3,6-didesoxy-D-xylo-hexose (abequose)]. Justus Liebigs Ann Chem. 1969;720:171-6. [PubMed:5798985 ]
  2. ZORBACH WW, CIAUDELLI JP: 2-DEOXY SUGARS. IV. 2,6-DIDEOXY-D-ARABINO-HEXOSE. J Org Chem. 1965 Feb;30:451-2. [PubMed:14267295 ]
  3. Horton D, Weckerle W: Synthesis of 3-amino-2,3,6-trideoxy-D-ribo-hexose hydrochloride. Carbohydr Res. 1976 Feb;46(2):227-35. [PubMed:1260789 ]
  4. Walker TE, Ehler DS, Unkefer CJ: Synthesis of 2-deoxy-D-arabino-(6-13C)hexose. Carbohydr Res. 1988 Oct 1;181:125-34. [PubMed:3208249 ]
  5. Fahrenheim G, Westphal O: [Para-nitro-phenylglycoside from 3-desoxy-D-arabino-, -D-ribo- and -D-xylo-hexose]. Justus Liebigs Ann Chem. 1969;720:177-87. [PubMed:5798986 ]
  6. Lehmann J, Schroter E: [Enzymatic conversion of 2-deoxy-D-lyxo-hexose (2-deoxy-D-galactose) to 3,6-anhydro-2-deoxy-D-lyxo-hexose (D-isogalactal)]. Carbohydr Res. 1974 Sep;36(2):303-10. [PubMed:4609608 ]
  7. Baer HH, Georges FF: A synthesis of 3-amino-2,3,6-trideoxy-D-ribo-hexose (D-ristosamine) hydrochloride. Carbohydr Res. 1977 May;55:253-8. [PubMed:193644 ]
  8. Kulhanek M, Tadra M, Linek K, Kucar S: 2-Deoxy-D-lyxo-hexonic acid from 2-deoxy-D-lyxo-hexose by Pseudomonas aeruginosa fermentation. Folia Microbiol (Praha). 1979;24(2):185-7. [PubMed:110658 ]
  9. Scruel O, Sener A, Malaisse WJ: Hexose metabolism in pancreatic islets: effect of D-glucose upon D-fructose metabolism. Mol Cell Biochem. 1999 Jul;197(1-2):209-16. [PubMed:10485341 ]
  10. Brimacombe JS, Portsmouth D: A synthesis of chromose D (3-O-acetyl-2,6-dideoxy-D-lyxo-hexose). Chem Ind. 1965 Mar 13;11:468. [PubMed:5825537 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
D-Glucopyranoside → 4-O-alpha-D-Glucopyranuronosyl-D-galactosedetails
D-Glucopyranoside → 3-O-beta-D-Galactopyranuronosyl-D-galactosedetails
D-Glucopyranoside → 2-O-beta-D-Glucopyranuronosyl-D-mannosedetails
D-Glucopyranoside → Acaciabiuronic aciddetails