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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:18:07 UTC
Update Date2017-12-07 18:49:31 UTC
HMDB IDHMDB0061098
Secondary Accession Numbers
  • HMDB61098
Metabolite Identification
Common Namealpha-dihydrotetrabenazine
Descriptionalpha-dihydrotetrabenazine is a metabolite of tetrabenazine. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder and is marketed under the trade names Nitoman in Canada and Xenazine in New Zealand and some parts of Europe, and is also available in the USA as an orphan drug. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntington's disease (HD), the first in the US. The compound has been known since the 1950s. (Wikipedia)
Structure
Thumb
SynonymsNot Available
Chemical FormulaC19H29NO3
Average Molecular Weight319.4385
Monoisotopic Molecular Weight319.214743799
IUPAC Name(2R,3S)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol
Traditional Name(2R,3S)-9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-ol
CAS Registry NumberNot Available
SMILES
COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1
InChI Identifier
InChI=1S/C19H29NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16?,17+/m0/s1
InChI KeyWEQLWGNDNRARGE-DRXWIORDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassTetrahydroisoquinolines
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Ether
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organic oxygen compound
  • Amine
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Organ and components:

Source:

Role

Biological role:

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 Solubility0.28 g/LALOGPS
logP2.98ALOGPS
logP2.67ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)14.85ChemAxon
pKa (Strongest Basic)8.27ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.93 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity92.4 m³·mol⁻¹ChemAxon
Polarizability37.17 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-0ufu-3292000000-616bc16f49d880cae9edView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-004i-8249000000-d0bbf8d456350af0aeefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0uk9-0009000000-9c277b99782b8216a454View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zmi-4059000000-c1e43ba5cc1445d72ed7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9160000000-55276a50fa5b351231c5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-09a82e4b00c48172cc45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-0039000000-8d2acd244003542952ffView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3940000000-60f86c3141ca9b72260fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      DrugBank Metabolite IDDBMET00458
      Phenol Explorer Compound IDNot Available
      Phenol Explorer Metabolite 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 CompoundNot Available
      PDB IDNot Available
      ChEBI IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available