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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2007-05-23 10:41:20 UTC
Update Date2020-02-26 21:26:25 UTC
HMDB IDHMDB0006468
Secondary Accession Numbers
  • HMDB06468
Metabolite Identification
Common Name4-Hydroxydebrisoquine
Description4-Hydroxydebrisoquine belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. 4-Hydroxydebrisoquine is a very strong basic compound (based on its pKa).
Structure
Data?1582752385
Synonyms
ValueSource
3,4-Dihydro-4-hydroxy-2(1H)-isoquinolinecarboximidamideChEBI
4 Hydroxy debrisoquineHMDB
4-Hydroxydebrisoquin sulfate (2:1)HMDB
4-HydroxydebrisoquinHMDB
4-HydroxydebrisoquineMeSH
Chemical FormulaC10H13N3O
Average Molecular Weight191.2297
Monoisotopic Molecular Weight191.105862053
IUPAC Name4-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboximidamide
Traditional Name4-hydroxydebrisoquine
CAS Registry Number59333-79-8
SMILES
NC(=N)N1CC(O)C2=C(C1)C=CC=C2
InChI Identifier
InChI=1S/C10H13N3O/c11-10(12)13-5-7-3-1-2-4-8(7)9(14)6-13/h1-4,9,14H,5-6H2,(H3,11,12)
InChI KeyAKFURXZANOMQBD-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassTetrahydroisoquinolines
Sub ClassNot Available
Direct ParentTetrahydroisoquinolines
Alternative Parents
Substituents
  • Tetrahydroisoquinoline
  • Benzenoid
  • Secondary alcohol
  • Guanidine
  • Azacycle
  • Carboximidamide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Imine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

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 Solubility1.06 g/LALOGPS
logP-0.27ALOGPS
logP0.06ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)14.04ChemAxon
pKa (Strongest Basic)12.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.06 m³·mol⁻¹ChemAxon
Polarizability20.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-2900000000-65d9860661c52fc43fedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-7930000000-6c547ba47e9a793be64aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-0900000000-d27d767387884b5344eeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-b4e6a4b85e95d2cd1a4dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kfx-9700000000-746c466d9e27ab653e6aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-0900000000-4a585452b243c3fa4da6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001j-0900000000-b7230e5ec4140e46052dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-0a94add8e365b703b0d3Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.217 +/- 0.021 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023927
KNApSAcK IDNot Available
Chemspider ID96842
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2299987
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107669
PDB IDNot Available
ChEBI ID63800
Food Biomarker OntologyNot Available
VMH ID4HDEBRISOQUINE
MarkerDB ID
References
Synthesis ReferenceRam, Siya; Saxena, Anil K.; Jain, Padam C. 2-Substituted 4-hydroxy-1,2,3,4-tetrahydroisoquinolines. Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry (1978), 16B(11), 1019-22.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Dorado P, Berecz R, Caceres MC, Gonzalez I, Cobaleda J, Llerena A: Determination of debrisoquine and 4-hydroxydebrisoquine by high-performance liquid chromatography: application to the evaluation of CYP2D6 genotype and debrisoquine metabolic ratio relationship. Clin Chem Lab Med. 2005;43(3):275-9. [PubMed:15843230 ]