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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:45 UTC
Update Date2019-01-11 19:46:07 UTC
HMDB IDHMDB0033103
Secondary Accession Numbers
  • HMDB33103
Metabolite Identification
Common Name(R)-Higenamine
Description(R)-Higenamine is found in coffee and coffee products. (R)-Higenamine is an alkaloid from the seed embryo of Nelumbo nucifera (East India lotus).
Structure
Data?1547235967
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, (+-)-isomerMeSH
Higenamine oxalate (1:1), (+-)-isomerMeSH
Higenamine, tartrate (1:1), R-(r*,r*)-(+-)-isomerMeSH
1-(P-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH
O-DemethylcoclaurineMeSH
Higenamine hydrochloride, (S)-isomerMeSH
1(S)-NorcoclaurineMeSH
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
DescriptionThis compound 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0900000000-6b4e08f9ac4d21085fe1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-0009600000-9b9f36994fbe2bc44955View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-96f0438a3c8200e429faView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074r-0950000000-0a5c9c204527cfedca3eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-d9dc7703828981b3c07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-22dffcee90bf3f5ca3ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-0fea9c480c329f5a864dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1910000000-1d1e1af6c74b76f1bc5bView in MoNA
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
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.. .