Human Metabolome Database Version 3.5

Showing metabocard for 3-Methoxy-4-hydroxyphenylethyleneglycol sulfate (HMDB00559)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-05-29 13:27:39 -0600
HMDB ID HMDB00559
Secondary Accession Numbers None
Metabolite Identification
Common Name 3-Methoxy-4-hydroxyphenylethyleneglycol sulfate
Description 3-methoxy-4-hydroxyphenylethyleneglycol sulfate (MHPG-SO4) is the major metabolite of noradrenaline in serum. Chronic schizophrenics have lower serum levels than healthy individuals. Treatment of both groups with 7 daily 3-mg doses of Haloperidol caused similar decreases in MHPG-SO4 concentration. (PMID 7343757 Link_out). In human urine, constitutes 44% of the total 3-methoxy-4-hydroxyphenylethylene glycol. (PMID 7379456 Link_out).
Structure Thumb
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Display: 2D Structure | 3D Structure
Synonyms
  1. (3-Methoxy-4-hydroxyphenyl)ethylene glycol sulfate
  2. (3-Methoxy-4-hydroxyphenyl)ethylene glycol sulphate
  3. (3-Methoxy-4-hydroxyphenyl)glycol O-sulfate
  4. (3-Methoxy-4-hydroxyphenyl)glycol O-sulphate
  5. (3-Methoxy-4-hydroxyphenyl)glycol sulfate ester
  6. (3-Methoxy-4-hydroxyphenyl)glycol sulphate ester
  7. 3-Methoxy-4-hydroxyphenylethyleneglycol sulfate
  8. 3-Methoxy-4-hydroxyphenylethyleneglycol sulphate
  9. 3-Methoxy-4-hydroxyphenylglycol 4-sulfate
  10. 3-Methoxy-4-hydroxyphenylglycol 4-sulphate
  11. MOPEG sulfate
  12. MOPEG sulphate
Chemical Formula C9H12O7S
Average Molecular Weight 264.252
Monoisotopic Molecular Weight 264.030373428
IUPAC Name [4-(1,2-dihydroxyethyl)-2-methoxyphenyl]oxidanesulfonic acid
Traditional IUPAC Name [4-(1,2-dihydroxyethyl)-2-methoxyphenyl]oxidanesulfonic acid
CAS Registry Number 3415-67-6
SMILES COC1=C(OS(O)(=O)=O)C=CC(=C1)C(O)CO
InChI Identifier InChI=1S/C9H12O7S/c1-15-9-4-6(7(11)5-10)2-3-8(9)16-17(12,13)14/h2-4,7,10-11H,5H2,1H3,(H,12,13,14)
InChI Key WUFPNASKMLJSND-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Phenols and Derivatives
Sub Class Tyrosols and Derivatives
Other Descriptors
  • Organic Compounds
Substituents
  • 1,2 Diol
  • Alkyl Aryl Ether
  • Anisole
  • Benzyl Alcohol Derivative
  • Organic Sulfuric Acid Monoester
  • Primary Alcohol
  • Secondary Alcohol
  • Sulfate Ester
Direct Parent Tyrosols and Derivatives
Ontology
Status Expected and Not 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 Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 4.11 g/L ALOGPS
LogP -1.51 ALOGPS
LogP -2.3 ChemAxon
LogS -1.81 ALOGPS
pKa (strongest acidic) -2.2 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 113.29 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 57.27 ChemAxon
Polarizability 24.14 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022119
KNApSAcK ID Not Available
Chemspider ID 4039 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00559 Link_out
Metagene Link HMDB00559 Link_out
METLIN ID 5543 Link_out
PubChem Compound 4183 Link_out
PDB ID Not Available
ChEBI ID 1091015 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Hoaki Y, Nishikawa T, Ida Y, Kohno Y, Tanaka M: Effect of haloperidol administration on serum MHPG-SO4 levels in chronic schizophrenics. Kurume Med J. 1981;28(3):197-200. Pubmed: 7343757 Link_out
  2. Boobis AR, Murray S, Jones DH, Reid JL, Davies DS: Urinary conjugates of 4-hydroxy-3-methoxyphenylethylene glycol do not provide an index of brain amine turnover in man. Clin Sci (Lond). 1980 Apr;58(4):311-6. Pubmed: 7379456 Link_out