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Showing Compound 5-Hydroxytryptophol glucuronide (FDB029328)

Record Information
Version1.0
Creation date2011-09-21 01:54:05 UTC
Update date2015-07-21 06:59:41 UTC
Primary IDFDB029328
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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 [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
5 Hydroxytryptophol glucuronideHMDB
5-Hydroxytryptophol glucuronideMeSH
5 hydroxytryptophol glucuronidehmdb
Predicted Properties
PropertyValueSource
Water Solubility4.05 g/LALOGPS
logP-0.52ALOGPS
logP-0.98ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area135.4 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.84 m³·mol⁻¹ChemAxon
Polarizability34.06 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H21NO7
IUPAC name(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
InChI IdentifierInChI=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
Isomeric SMILESOCCC1=CNC2=C1C=C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2
Average Molecular Weight339.3404
Monoisotopic Molecular Weight339.131802031
Classification
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
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS5-Hydroxytryptophol glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-9557000000-89dd3aa0241b0128cd5eSpectrum
Predicted GC-MS5-Hydroxytryptophol glucuronide, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-4232139000-84fe6528bd78b5a69576Spectrum
Predicted GC-MS5-Hydroxytryptophol glucuronide, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03ml-0907000000-178fc463cf5bc07086a72017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-d8b916eff323e05f80eb2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-1900000000-5e05797ce3689ac582fe2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0550-0719000000-b1be2b51a0a1106559492017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-0912000000-21445bc710ab56eb35912017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057l-1900000000-26dcaa4e63466af6bb8d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0209000000-e9a1ea04a4dcc2569a6b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-3917000000-caeeebd4ebe3b97657322021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5c-2911000000-bdec3b3526b152485e042021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0409000000-845ab1b873508a28afc52021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022d-0976000000-c0d6297d29b646dbaaad2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01b9-4890000000-fb016c36287a8170c4e72021-09-22View Spectrum
NMRNot Available
ChemSpider ID30776699
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53481648
Pubchem Substance IDNot Available
ChEBI ID32649
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB13200
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference