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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:53:45 UTC
Update Date2022-03-07 02:53:36 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 sweet, fruity, and milky tasting compound (R)-Higenamine has been detected, but not quantified in, custard apples (Annona reticulata) and opium poppies (Papaver somniferum). This could make (R)-higenamine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Higenamine.
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, (+-)-isomerMeSH, HMDB
Higenamine oxalate (1:1), (+-)-isomerMeSH, HMDB
Higenamine, tartrate (1:1), R-(r*,r*)-(+-)-isomerMeSH, HMDB
1-(P-Hydroxybenzyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinolineMeSH, HMDB
O-DemethylcoclaurineMeSH, HMDB
Higenamine hydrochloride, (S)-isomerMeSH, HMDB
1(S)-NorcoclaurineMeSH, HMDB
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
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point242 - 244 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+165.44231661259
DarkChem[M-H]-163.89431661259
DeepCCS[M+H]+166.50130932474
DeepCCS[M-H]-164.14330932474
DeepCCS[M-2H]-197.02930932474
DeepCCS[M+Na]+172.59430932474
AllCCS[M+H]+165.532859911
AllCCS[M+H-H2O]+161.732859911
AllCCS[M+NH4]+168.932859911
AllCCS[M+Na]+169.932859911
AllCCS[M-H]-168.132859911
AllCCS[M+Na-2H]-167.832859911
AllCCS[M+HCOO]-167.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-HigenamineOC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C13436.2Standard polar33892256
(R)-HigenamineOC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C12823.3Standard non polar33892256
(R)-HigenamineOC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C13001.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Higenamine,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C32)C=C12813.5Semi standard non polar33892256
(R)-Higenamine,1TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2CC1=CC=C(O)C=C12813.9Semi standard non polar33892256
(R)-Higenamine,1TMS,isomer #3C[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC22811.7Semi standard non polar33892256
(R)-Higenamine,1TMS,isomer #4C[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1CC1=CC=C(O)C=C12901.9Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C)=C(O)C=C32)C=C12713.2Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O[Si](C)(C)C)C=C32)C=C12715.3Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #3C[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C)C=C12796.5Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)NCC22775.7Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #5C[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C)C2CC1=CC=C(O)C=C12773.2Semi standard non polar33892256
(R)-Higenamine,2TMS,isomer #6C[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C)CC22788.0Semi standard non polar33892256
(R)-Higenamine,3TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C32)C=C12775.2Semi standard non polar33892256
(R)-Higenamine,3TMS,isomer #2C[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C12759.1Semi standard non polar33892256
(R)-Higenamine,3TMS,isomer #3C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C)C=C12748.7Semi standard non polar33892256
(R)-Higenamine,3TMS,isomer #4C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C)CC22751.3Semi standard non polar33892256
(R)-Higenamine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C12809.5Semi standard non polar33892256
(R)-Higenamine,4TMS,isomer #1C[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C3CCN2[Si](C)(C)C)C=C12729.7Standard non polar33892256
(R)-Higenamine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O)C=C32)C=C13097.6Semi standard non polar33892256
(R)-Higenamine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCNC2CC1=CC=C(O)C=C13098.8Semi standard non polar33892256
(R)-Higenamine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC23102.0Semi standard non polar33892256
(R)-Higenamine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1CCC2=CC(O)=C(O)C=C2C1CC1=CC=C(O)C=C13173.1Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C32)C=C13243.7Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C13246.5Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C13318.5Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)NCC23276.6Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)CCN([Si](C)(C)C(C)(C)C)C2CC1=CC=C(O)C=C13304.4Semi standard non polar33892256
(R)-Higenamine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)CC23307.3Semi standard non polar33892256
(R)-Higenamine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2NCCC3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C32)C=C13470.0Semi standard non polar33892256
(R)-Higenamine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C13495.0Semi standard non polar33892256
(R)-Higenamine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C13498.3Semi standard non polar33892256
(R)-Higenamine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(CC1=CC=C(O)C=C1)N([Si](C)(C)C(C)(C)C)CC23482.3Semi standard non polar33892256
(R)-Higenamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C13724.0Semi standard non polar33892256
(R)-Higenamine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CC2C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C3CCN2[Si](C)(C)C(C)(C)C)C=C13527.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Higenamine GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-0900000000-6b4e08f9ac4d21085fe12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Higenamine GC-MS (3 TMS) - 70eV, Positivesplash10-0ab9-0009600000-9b9f36994fbe2bc449552017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Higenamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Higenamine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Positive-QTOFsplash10-00di-0190000000-96f0438a3c8200e429fa2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Positive-QTOFsplash10-074r-0950000000-0a5c9c204527cfedca3e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Positive-QTOFsplash10-0a6r-3900000000-d9dc7703828981b3c07c2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Negative-QTOFsplash10-00di-0090000000-22dffcee90bf3f5ca3cc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Negative-QTOFsplash10-00di-0190000000-0fea9c480c329f5a864d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Negative-QTOFsplash10-03di-1910000000-1d1e1af6c74b76f1bc5b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Positive-QTOFsplash10-00di-0090000000-0ce88f6c7aacd22857e82021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Positive-QTOFsplash10-00di-0290000000-4d665e8a013041d3e4c62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Positive-QTOFsplash10-0f76-4790000000-ad87407e83862f6905892021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 10V, Negative-QTOFsplash10-00di-0090000000-19dbfadd3d4c178682782021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 20V, Negative-QTOFsplash10-00di-0190000000-89e3c768495d58f4e18c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Higenamine 40V, Negative-QTOFsplash10-008d-1920000000-910f9db17a9a05be60452021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents 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.. .