You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:15 UTC
HMDB IDHMDB0000496
Secondary Accession Numbers
  • HMDB00496
Metabolite Identification
Common Name3-Methoxy-4-hydroxyphenylglycol glucuronide
Description3-Methoxy-4-hydroxyphenylglycol glucuronide, also known as MHPG glucuronide, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 3-Methoxy-4-hydroxyphenylglycol glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Data?1582752135
Synonyms
ValueSource
MHPG GlucuronideHMDB
(2S,3S,4S,5R,6S)-6-[4-(1,2-Dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylateHMDB
3-Methoxy-4-hydroxyphenylglycol glucuronideMeSH
Chemical FormulaC15H20O10
Average Molecular Weight360.3133
Monoisotopic Molecular Weight360.10564686
IUPAC Name(2S,3S,4S,5R,6S)-6-[4-(1,2-dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Namemhpg glucuronide
CAS Registry Number52002-41-2
SMILES
COC1=CC(=CC=C1O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O)C(O)CO
InChI Identifier
InChI=1S/C15H20O10/c1-23-9-4-6(7(17)5-16)2-3-8(9)24-15-12(20)10(18)11(19)13(25-15)14(21)22/h2-4,7,10-13,15-20H,5H2,1H3,(H,21,22)/t7?,10-,11-,12+,13-,15+/m0/s1
InChI KeyVMWCOZPKGQMCRO-UICVJNQZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • 1-o-glucuronide
  • O-glucuronide
  • Glucuronic acid or derivatives
  • Hexose monosaccharide
  • O-glycosyl compound
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Beta-hydroxy acid
  • Monosaccharide
  • Hydroxy acid
  • Pyran
  • Oxane
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Carboxylic acid
  • Ether
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic alcohol
  • Primary alcohol
  • Organic oxide
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.6 g/LALOGPS
logP-1.6ALOGPS
logP-1.8ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.11ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity79.29 m³·mol⁻¹ChemAxon
Polarizability33.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8369000000-38eb7f3b8b8b7ce0d6bdSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-3542059000-16032c3306e5a21d1276Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-029l-0906000000-102c4a0b9fc260913ad7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-0900000000-a7cfde852530158d455dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-0900000000-083c4bc276665344a107Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0api-2719000000-32a87140eafd1662087fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1932000000-2529a0237453fcab4ad3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00si-3900000000-41be27fec598029b3071Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineDetected and Quantified0.18 +/- 0.022 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified0.15 +/- 0.015 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified0.081+/- 0.012 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    Phenol Explorer Compound IDNot Available
    FooDB IDFDB022075
    KNApSAcK IDNot Available
    Chemspider ID17215958
    KEGG Compound IDC03033
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID1593
    PubChem Compound22833525
    PDB IDNot Available
    ChEBI ID89405
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Not Available
    General References
    1. Shimizu H, LaBrosse EH: Metabolism of catecholamines--identification and quantification of 3-methoxy-4-hydroxyphenylglycol glucuronide in human urine. Biochem Pharmacol. 1969 Jul;18(7):1643-54. [PubMed:5806107 ]
    2. Muller HU, Riemann D, Berger M, Muller WE: The influence of total sleep deprivation on urinary excretion of catecholamine metabolites in major depression. Acta Psychiatr Scand. 1993 Jul;88(1):16-20. [PubMed:8396844 ]
    3. Peyrin L, Pequignot JM, Lacour JR, Fourcade J: Relationships between catecholamine or 3-methoxy 4-hydroxy phenylglycol changes and the mental performance under submaximal exercise in man. Psychopharmacology (Berl). 1987;93(2):188-92. [PubMed:3122251 ]
    4. Buchanan DN, Fucek FR, Domino EF: Analysis of urinary 4-hydroxy-3-methoxyphenylethylene glycol as vanillyl alcohol by high-performance liquid chromatography with amperometric detection. J Chromatogr. 1979 Mar 1;162(3):394-400. [PubMed:528605 ]

    Only showing the first 10 proteins. There are 18 proteins in total.

    Enzymes

    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
    Gene Name:
    UGT2B28
    Uniprot ID:
    Q9BY64
    Molecular weight:
    38742.9
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
    Gene Name:
    UGT2B4
    Uniprot ID:
    P06133
    Molecular weight:
    60512.035
    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.
    Gene Name:
    UGT1A4
    Uniprot ID:
    P22310
    Molecular weight:
    60024.535
    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. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
    Gene Name:
    UGT2B7
    Uniprot ID:
    P16662
    Molecular weight:
    60720.15
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
    Gene Name:
    UGT2B15
    Uniprot ID:
    P54855
    Molecular weight:
    61035.815
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
    Gene Name:
    UGT2A1
    Uniprot ID:
    Q9Y4X1
    Molecular weight:
    60771.605
    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
    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 has specificity for phenols.
    Gene Name:
    UGT1A9
    Uniprot ID:
    O60656
    Molecular weight:
    59940.495
    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.
    Gene Name:
    UGT1A3
    Uniprot ID:
    P35503
    Molecular weight:
    60337.835
    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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
    Gene Name:
    UGT2B17
    Uniprot ID:
    O75795
    Molecular weight:
    61094.915

    Only showing the first 10 proteins. There are 18 proteins in total.