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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:45 UTC
Update Date2019-07-23 06:12:33 UTC
HMDB IDHMDB0033103
Secondary Accession Numbers
  • HMDB33103
Metabolite Identification
Common Name(R)-Higenamine
Description(R)-Higenamine, also known as norcoclaurine, belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached (R)-Higenamine is a very strong basic compound (based on its pKa) (R)-Higenamine is a sweet, fruity, and milky tasting compound. Outside of the human body, (R)-Higenamine has been detected, but not quantified in, custard apples and opium poppies. This could make (R)-higenamine a potential biomarker for the consumption of these foods. Higenamine is under investigation in clinical trial NCT01451229 (Pharmacokinetics and Pharmacodynamics of Higenamine in Chinese Healthy Subjects).
Structure
Data?1563862353
Synonyms
ValueSource
(+-)-1,2,3,4-Tetrahydro-1-((4-hydroxyphenyl)methyl)-6,7-isoquinolinediolChEBI
(+-)-DemethylcoclaurineChEBI
(+-)-NorcoclaurineChEBI
(+-)-O-DemethylcoclaurineChEBI
(R,S)-NorcoclaurineChEBI
6,7-Dihydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolineChEBI
HigenamineChEBI
NorcoclaurineChEBI
(+)-DemethylcoclaurineHMDB
(R)-NorcoclaurineHMDB
Higenamine hydrobromide, (+-)-isomerHMDB
Higenamine oxalate (1:1), (+-)-isomerHMDB
Higenamine, tartrate (1:1), R-(r*,r*)-(+-)-isomerHMDB
1-(p-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineHMDB
O-DemethylcoclaurineHMDB
Higenamine hydrochloride, (S)-isomerHMDB
1(S)-NorcoclaurineHMDB
Chemical FormulaC16H17NO3
Average Molecular Weight271.3111
Monoisotopic Molecular Weight271.120843415
IUPAC Name1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
Traditional Namehigenamine
CAS Registry Number106032-53-5
SMILES
OC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1
InChI Identifier
InChI=1S/C16H17NO3/c18-12-3-1-10(2-4-12)7-14-13-9-16(20)15(19)8-11(13)5-6-17-14/h1-4,8-9,14,17-20H,5-7H2
InChI KeyWZRCQWQRFZITDX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoquinolines and derivatives
Sub ClassBenzylisoquinolines
Direct ParentBenzylisoquinolines
Alternative Parents
Substituents
  • Benzylisoquinoline
  • Tetrahydroisoquinoline
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Monocyclic benzene moiety
  • Benzenoid
  • Secondary aliphatic amine
  • Secondary amine
  • Azacycle
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point242 - 244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.24 g/LALOGPS
logP1.73ALOGPS
logP2.23ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)8.75ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area72.72 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.6 m³·mol⁻¹ChemAxon
Polarizability29.25 ųChemAxon
Number of Rings3ChemAxon
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, Positivesplash10-03di-0900000000-6b4e08f9ac4d21085fe1Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-0009600000-9b9f36994fbe2bc44955Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-96f0438a3c8200e429faSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074r-0950000000-0a5c9c204527cfedca3eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-d9dc7703828981b3c07cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-22dffcee90bf3f5ca3ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-0fea9c480c329f5a864dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1910000000-1d1e1af6c74b76f1bc5bSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12779
Phenol Explorer Compound IDNot Available
FooDB IDFDB011811
KNApSAcK IDC00049556
Chemspider ID102800
KEGG Compound IDC06346
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound114840
PDB IDNot Available
ChEBI ID18418
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .