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Showing Compound (S)-Higenamine (FDB011811)

Record Information
Version1.0
Creation date2010-04-08 22:09:50 UTC
Update date2019-11-26 03:05:28 UTC
Primary IDFDB011811
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(S)-Higenamine
DescriptionHigenamine, also known as norcoclaurine or (+-)-demethylcoclaurine, is a member of the class of compounds known as benzylisoquinolines. Benzylisoquinolines are organic compounds containing an isoquinoline to which a benzyl group is attached. Higenamine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Higenamine is a sweet, fruity, and milky tasting compound found in custard apple and opium poppy, which makes higenamine a potential biomarker for the consumption of these food products. Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum (stem and vine), Annona squamosa, and Nelumbo nucifera (lotus seeds) .
CAS Number22672-77-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(+-)-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
(S)-(-)-Higenaminebiospider
(s)-norcoclaurinebiospider
S-norcoclaurinebiospider
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
Chemical FormulaC16H17NO3
IUPAC name1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol
InChI IdentifierInChI=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
Isomeric SMILESOC1=CC=C(CC2NCCC3=C2C=C(O)C(O)=C3)C=C1
Average Molecular Weight271.3111
Monoisotopic Molecular Weight271.120843415
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.83%; H 6.32%; N 5.16%; O 17.69%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(R)-Higenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03di-0900000000-6b4e08f9ac4d21085fe1Spectrum
Predicted GC-MS(R)-Higenamine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-0009600000-9b9f36994fbe2bc44955Spectrum
Predicted GC-MS(R)-Higenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS(R)-Higenamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0190000000-96f0438a3c8200e429fa2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-074r-0950000000-0a5c9c204527cfedca3e2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3900000000-d9dc7703828981b3c07c2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-22dffcee90bf3f5ca3cc2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-0fea9c480c329f5a864d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-1910000000-1d1e1af6c74b76f1bc5b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0090000000-0ce88f6c7aacd22857e82021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0290000000-4d665e8a013041d3e4c62021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f76-4790000000-ad87407e83862f6905892021-09-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-19dbfadd3d4c178682782021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0190000000-89e3c768495d58f4e18c2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-008d-1920000000-910f9db17a9a05be60452021-09-25View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06160
Pubchem Compound ID44229138
Pubchem Substance IDNot Available
ChEBI ID32110
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHGP94-O:GZK81-B
EAFUS IDNot Available
Dr. Duke IDNORCOCLAURINE
BIGG IDNot Available
KNApSAcK IDC00034613
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1555481
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
fruity
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
milky
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.