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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-21 08:10:09 UTC
Update Date2023-02-21 17:15:50 UTC
HMDB IDHMDB0001855
Secondary Accession Numbers
  • HMDB01855
Metabolite Identification
Common Name5-Hydroxytryptophol
Description5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112 ).
Structure
Data?1676999750
Synonyms
ValueSource
5-HTOLHMDB
5-Hydroxy-1H-indole-3-ethanolHMDB
5-Hydroxy-1H-indole-3-ethanol(9ci)HMDB
5-Hydroxy-3-indoleHMDB
5-Hydroxy-3-indoleacetic acidHMDB
5-Hydroxy-indole-acetic acidHMDB
5-Hydroxyindoacetic acidHMDB
5-HydroxyindolHMDB
5-HydroxyindolacetateHMDB
5-Hydroxyindolacetic acidHMDB
5-Hydroxyindole-3-ethanolHMDB
5-Hydroxyindole-acetic acidHMDB
Hydroxyindoleacetic acidHMDB
HydroxytryptopholHMDB, MeSH
Chemical FormulaC10H11NO2
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
IUPAC Name3-(2-hydroxyethyl)-1H-indol-5-ol
Traditional Namehydroxytryptophol
CAS Registry Number154-02-9
SMILES
OCCC1=CNC2=CC=C(O)C=C12
InChI Identifier
InChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
InChI KeyKQROHCSYOGBQGJ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available134.491http://allccs.zhulab.cn/database/detail?ID=AllCCS00000343
[M+H]+Not Available138.754http://allccs.zhulab.cn/database/detail?ID=AllCCS00000343
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.18 g/LALOGPS
logP0.91ALOGPS
logP1.29ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)9.56ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area56.25 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity50.7 m³·mol⁻¹ChemAxon
Polarizability18.86 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+138.3131661259
DarkChem[M-H]-138.55631661259
AllCCS[M+H]+138.69232859911
AllCCS[M-H]-138.90532859911
DeepCCS[M-2H]-170.79230932474
DeepCCS[M+Na]+146.33130932474
AllCCS[M+H]+138.732859911
AllCCS[M+H-H2O]+134.332859911
AllCCS[M+NH4]+142.832859911
AllCCS[M+Na]+144.032859911
AllCCS[M-H]-138.932859911
AllCCS[M+Na-2H]-139.332859911
AllCCS[M+HCOO]-139.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.83 minutes32390414
Predicted by Siyang on May 30, 20229.4801 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.5 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid29.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1255.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid301.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid96.1 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid163.3 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid204.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid299.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid260.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)139.6 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid640.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid264.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid996.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid272.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid225.3 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate530.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA255.9 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water181.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-HydroxytryptopholOCCC1=CNC2=CC=C(O)C=C123295.9Standard polar33892256
5-HydroxytryptopholOCCC1=CNC2=CC=C(O)C=C122018.6Standard non polar33892256
5-HydroxytryptopholOCCC1=CNC2=CC=C(O)C=C122090.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxytryptophol,1TMS,isomer #1C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C122096.0Semi standard non polar33892256
5-Hydroxytryptophol,1TMS,isomer #2C[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C12026.3Semi standard non polar33892256
5-Hydroxytryptophol,1TMS,isomer #3C[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C212087.7Semi standard non polar33892256
5-Hydroxytryptophol,2TMS,isomer #1C[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C122063.7Semi standard non polar33892256
5-Hydroxytryptophol,2TMS,isomer #2C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122112.9Semi standard non polar33892256
5-Hydroxytryptophol,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C2070.4Semi standard non polar33892256
5-Hydroxytryptophol,3TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122099.5Semi standard non polar33892256
5-Hydroxytryptophol,3TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122173.8Standard non polar33892256
5-Hydroxytryptophol,3TMS,isomer #1C[Si](C)(C)OCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122147.5Standard polar33892256
5-Hydroxytryptophol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O)C=C122366.6Semi standard non polar33892256
5-Hydroxytryptophol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C2[NH]C=C(CCO)C2=C12313.5Semi standard non polar33892256
5-Hydroxytryptophol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C=C(CCO)C2=CC(O)=CC=C212354.7Semi standard non polar33892256
5-Hydroxytryptophol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122585.6Semi standard non polar33892256
5-Hydroxytryptophol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122599.2Semi standard non polar33892256
5-Hydroxytryptophol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)C(CCO)=CN2[Si](C)(C)C(C)(C)C2583.4Semi standard non polar33892256
5-Hydroxytryptophol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122801.7Semi standard non polar33892256
5-Hydroxytryptophol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122796.0Standard non polar33892256
5-Hydroxytryptophol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122478.9Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0009 +/- 0.0003 uMAdult (>18 years old)BothNormal details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.004 +/- 0.22 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified0.107 +/- 0.019 uMNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Cerebrospinal Fluid (CSF)Detected and Quantified0.12 +/- 0.09 uMChildren (1-13 years old)Not SpecifiedLeukemia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.009 +/- 0.01 uMNot SpecifiedNot SpecifiedNeurological disorders (2 - 18 years old) details
Cerebrospinal Fluid (CSF)Detected and Quantified0.11 +/- 0.013 uMAdult (>18 years old)FemaleSchizophrenia details
Cerebrospinal Fluid (CSF)Detected and Quantified0.0846 +/- 0.0179 uMAdult (>18 years old)Not SpecifiedParkinson's Disease details
Associated Disorders and Diseases
Disease References
Leukemia
  1. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
Schizophrenia
  1. Harnryd C, Bjerkenstedt L, Grimm VE, Sedvall G: Reduction of MOPEG levels in cerebrospinal fluid of psychotic women after electroconvulsive treatment. Psychopharmacology (Berl). 1979 Aug 8;64(2):131-4. [PubMed:115032 ]
Parkinson's disease
  1. Dizdar N, Kagedal B, Lindvall B: Treatment of Parkinson's disease with NADH. Acta Neurol Scand. 1994 Nov;90(5):345-7. [PubMed:7887134 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022711
KNApSAcK IDC00045185
Chemspider ID8708
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5730
PubChem Compound9061
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDCE1918
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceDa Prada, M.; Bartholini, G.; Pletscher, A. Formation of 5-hydroxytryptophol by blood platelets after thrombin and reserpine. Experientia (1965), 21(3), 135-6.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Curtius HC, Wolfensberger M, Redweik U, Leimbacher W, Maibach RA, Isler W: Mass fragmentography of 5-hydroxytryptophol and 5-methoxytryptophol in human cerebrospinal fluid. J Chromatogr. 1975 Oct 29;112:523-31. [PubMed:1184685 ]
  2. Krishnaswamy S, Hao Q, Von Moltke LL, Greenblatt DJ, Court MH: Evaluation of 5-hydroxytryptophol and other endogenous serotonin (5-hydroxytryptamine) analogs as substrates for UDP-glucuronosyltransferase 1A6. Drug Metab Dispos. 2004 Aug;32(8):862-9. [PubMed:15258112 ]