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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2013-03-04 20:35:15 UTC
Update Date2017-12-07 15:52:40 UTC
HMDB IDHMDB0059805
Secondary Accession Numbers
  • HMDB59805
Metabolite Identification
Common Name5-Hydroxyindole
Description5-hydroxyindole, also known as indol-5-ol, is a member of the class of compounds known as hydroxyindoles. Hydroxyindoles are organic compounds containing an indole moiety that carries a hydroxyl group. 5-hydroxyindole is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxyindole can be found primarily in blood and feces. This compound belongs to the family of Indoles and Derivatives. These are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole..
Structure
Thumb
SynonymsNot Available
Chemical FormulaC8H7NO
Average Molecular Weight133.1473
Monoisotopic Molecular Weight133.052763851
IUPAC Name1H-indol-5-ol
Traditional Name5-hydroxyindol
CAS Registry NumberNot Available
SMILES
OC1=CC=C2NC=CC2=C1
InChI Identifier
InChI=1S/C8H7NO/c10-7-1-2-8-6(5-7)3-4-9-8/h1-5,9-10H
InChI KeyLMIQERWZRIFWNZ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot 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 Solubility6.2 g/LALOGPS
logP1.53ALOGPS
logP1.77ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.57ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.13 m³·mol⁻¹ChemAxon
Polarizability13.8 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-001i-1900000000-1094a4ccc9b307e495bfView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ec-7910000000-ef710634e23a379a8f2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-26b6117bdecb9eeeb974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0900000000-6d10c5d675ddbc00cbb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-7900000000-6be33c39410d4c6bdefcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0900000000-29059f2d22bf687da060View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-ed9904f0ec5efd6415cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2900000000-f0a6080ff8696c41901cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Not SpecifiedNot Specified
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not Quantified Adult (>18 years old)BothHemodialysis patients with colon details
BloodDetected but not Quantified Adult (>18 years old)Not AvailableHemodialysis patients without colon. details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16054
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Aronov PA, Luo FJ, Plummer NS, Quan Z, Holmes S, Hostetter TH, Meyer TW: Colonic contribution to uremic solutes. J Am Soc Nephrol. 2011 Sep;22(9):1769-76. doi: 10.1681/ASN.2010121220. Epub 2011 Jul 22. [PubMed:21784895 ]
  2. Phua LC, Koh PK, Cheah PY, Ho HK, Chan EC: Global gas chromatography/time-of-flight mass spectrometry (GC/TOFMS)-based metabonomic profiling of lyophilized human feces. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Oct 15;937:103-13. doi: 10.1016/j.jchromb.2013.08.025. Epub 2013 Aug 26. [PubMed:24029555 ]
  3. Ashcroft GW, Eccleston D, Crawford TB: 5-hydroxyindole metabolism in rat brain. A study of intermediate metabolism using the technique of tryptophan loading. I. Methods. J Neurochem. 1965 Jun;12(6):483-92. [PubMed:5294372 ]
  4. Eccleston D, Ashcroft GW, Crawford TB: 5-hydroxyindole metabolism in rat brain. A study of intermediate metabolism using the technique of tryptophan loading. II. Applications and drug studies. J Neurochem. 1965 Jun;12(6):493-503. [PubMed:5294373 ]