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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-11-30 15:50:51 UTC
Update Date2021-09-14 14:58:16 UTC
HMDB IDHMDB0013200
Secondary Accession Numbers
  • HMDB13200
Metabolite Identification
Common Name5-Hydroxytryptophol glucuronide
Description5-Hydroxytryptophol glucuronide (GTOL) is the major excretion form of 5-hydroxytryptophol (5-HTOL), a minor serotonin metabolite under normal conditions. Because the concentration of 5-HTOL is markedly increased following consumption of alcohol, measurement of 5-HTOL is used as a sensitive biomarker for detection of recent alcohol intake. PMID: 15664340 . 5-Hydroxytryptophol glucuronide provided higher diagnostic specificity and sensitivity than 5-hydroxytryptophol. PMID: 17112495 .
Structure
Thumb
Synonyms
ValueSource
5 Hydroxytryptophol glucuronideHMDB
5-Hydroxytryptophol glucuronideMeSH
Chemical FormulaC16H21NO7
Average Molecular Weight339.3404
Monoisotopic Molecular Weight339.131802031
IUPAC Name(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
Traditional Name(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
CAS Registry NumberNot Available
SMILES
OCCC1=CNC2=C1C=C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2
InChI Identifier
InChI=1S/C16H21NO7/c18-4-3-8-6-17-11-2-1-9(5-10(8)11)23-16-15(22)14(21)13(20)12(7-19)24-16/h1-2,5-6,12-22H,3-4,7H2/t12-,13-,14+,15-,16+/m1/s1
InChI KeyMYNVMBICAGQOMG-LJIZCISZSA-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
  • Hexose monosaccharide
  • O-glycosyl compound
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • Monosaccharide
  • Oxane
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Secondary alcohol
  • Polyol
  • Azacycle
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Alcohol
  • Primary alcohol
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029328
KNApSAcK IDNot Available
Chemspider ID30776699
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481648
PDB IDNot Available
ChEBI ID166506
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Stephanson N, Dahl H, Helander A, Beck O: Determination of urinary 5-hydroxytryptophol glucuronide by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Feb 25;816(1-2):107-12. [PubMed:15664340 ]
  2. Dierkes J, Wolfersdorf M, Borucki K, Weinmann W, Wiesbeck G, Beck O, Borg S, Wurst FM: Determination of glucuronidated 5-hydroxytryptophol (GTOL), a marker of recent alcohol intake, by ELISA technique. Clin Biochem. 2007 Jan;40(1-2):128-31. Epub 2006 Oct 20. [PubMed:17112495 ]