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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-24 12:53:30 UTC
Update Date2017-10-23 19:04:12 UTC
HMDB IDHMDB0004817
Secondary Accession Numbers
  • HMDB04817
Metabolite Identification
Common Name5-Hydroxydopamine
Description5-Hydroxydopamine is a naturally occurring amine in human urine. 5-Hydroxydopamine concentration in urine of DOPA treated Parkinson's patients was significantly higher than inpatients not treated or normal controls. (PMID 8255370 ).
Structure
Thumb
Synonyms
ValueSource
3,4,5-TrihydroxyphenethylamineHMDB
3,4,5-TrihydroxyphenylethylamineHMDB
5-(2-Aminoethyl)-pyrogallolHMDB
5-(2-Aminoethyl)1,2,3-benzenetriolHMDB
5-(2-Aminoethyl)benzene-1,2,3-triolHMDB
5-Hydroxydopamine hydrobromideMeSH
5-Hydroxydopamine hydrochlorideMeSH
Chemical FormulaC8H11NO3
Average Molecular Weight169.1778
Monoisotopic Molecular Weight169.073893223
IUPAC Name5-(2-aminoethyl)benzene-1,2,3-triol
Traditional Name5-hydroxydopamine
CAS Registry Number1927-04-4
SMILES
NCCC1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C8H11NO3/c9-2-1-5-3-6(10)8(12)7(11)4-5/h3-4,10-12H,1-2,9H2
InChI KeyLCAINUZZHIZKKS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as catecholamines and derivatives. These are compounds containing 4-(2-Aminoethyl)pyrocatechol [4-(2-aminoethyl)benzene-1,2-diol] or a derivative thereof formed by substitution.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassPhenols
Direct ParentCatecholamines and derivatives
Alternative Parents
Substituents
  • Catecholamine
  • Benzenetriol
  • Phenethylamine
  • Pyrogallol derivative
  • 2-arylethylamine
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Monocyclic benzene moiety
  • Polyol
  • Amine
  • Primary amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.52 g/LALOGPS
logP-0.83ALOGPS
logP-0.42ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)9.9ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area86.71 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.23 m³·mol⁻¹ChemAxon
Polarizability17.11 ųChemAxon
Number of Rings1ChemAxon
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-8900000000-3261e8bbf7b3af54c5cbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00di-5739000000-507d8522f66b456a2fd6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0900000000-8e04fc6997168bc535daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1900000000-2a81a3333366e5ba8665View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9600000000-cb25b7126b075715bba3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-0ff3d26d1aa3f40c71fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-6194485699cb58a6436cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvu-7900000000-261c0ce84c54c101a6dfView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.1(0.06-0.13) umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease ReferencesNone
    Associated OMIM IDsNone
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023427
    KNApSAcK IDNot Available
    Chemspider ID102750
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID7081
    PubChem Compound114772
    PDB IDNot Available
    ChEBI ID144646
    References
    Synthesis ReferenceNot Available
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Andrew R, Watson DG, Best SA, Midgley JM, Wenlong H, Petty RK: The determination of hydroxydopamines and other trace amines in the urine of parkinsonian patients and normal controls. Neurochem Res. 1993 Nov;18(11):1175-7. [PubMed:8255370 ]