Record Information
Version1.0
Creation date2010-04-08 22:09:50 UTC
Update date2018-05-28 23:31:48 UTC
Primary IDFDB011812
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCoclaurine
DescriptionCoclaurine, also known as (r,s)-coclaurine or machiline, 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. Coclaurine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Coclaurine can be found in custard apple and soursop, which makes coclaurine a potential biomarker for the consumption of these food products. Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum, Ocotea duckei, and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine .
CAS Number2196-60-3
Structure
Thumb
Synonyms
SynonymSource
(R,S)-CoclaurineChEBI
6-Methoxy-7-hydroxy-1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinolineChEBI
DL-CoclaurineKegg
MachilineKegg
CoclaurineChEBI
(+)-1(R)-Coclaurinebiospider
(+)-Coclaurinebiospider
(+)-R-Coclaurinebiospider
(R)-Coclaurinebiospider
D-coclaurinebiospider
Sanjoinine Kdb_source
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.2ALOGPS
logP2.51ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.92ChemAxon
pKa (Strongest Basic)8.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.72 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity82.08 m³·mol⁻¹ChemAxon
Polarizability31.31 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC17H19NO3
IUPAC name1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
InChI IdentifierInChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3
InChI KeyLVVKXRQZSRUVPY-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
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
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Secondary amine
  • Ether
  • Secondary aliphatic amine
  • Azacycle
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen 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 71.56%; H 6.71%; N 4.91%; O 16.82%DFC
Melting PointMp 217-218°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +47 (EtOH)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0190000000-c51f7399519ef56e73baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0699-0950000000-4a1f90323b9937adb67bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-3900000000-60e9e4b45ae16bb78dc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-4d22fc04b303cacd4270View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-4279946a636b9df45307View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dj-0930000000-40765f612e0f0de506c9View in MoNA
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC06349
Pubchem Compound ID440989
Pubchem Substance IDNot Available
ChEBI ID18417
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHGP94-O:GZK82-C
EAFUS IDNot Available
Dr. Duke IDCOCLAURINE
BIGG IDNot Available
KNApSAcK IDC00025652
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
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 / Bioactivities
DescriptorIDDefinitionReference
anti aggregantDUKE
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
anti radicularDUKE
cytotoxic52209 A role played by the molecular entity or part thereof which causes the development of a pathological process.DUKE
depressantDUKE
hypothermicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
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).