1.02010-04-08 22:09:50 UTC2019-11-26 03:05:28 UTCFDB011812CoclaurineCoclaurine, 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 .(+)-1(R)-Coclaurine(+)-Coclaurine(+)-R-Coclaurine(R)-CoclaurineCoclaurineD-coclaurineMachilineSanjoinine KC17H19NO3285.3377285.1364934791-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol(RS)-coclaurine2196-60-3COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2InChI=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,6-8H2,1H3LVVKXRQZSRUVPY-UHFFFAOYSA-N belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.BenzylisoquinolinesOrganic compoundsOrganoheterocyclic compoundsIsoquinolines and derivativesBenzylisoquinolinesAromatic heteropolycyclic compounds1-hydroxy-2-unsubstituted benzenoidsAlkyl aryl ethersAnisolesAralkylaminesAzacyclic compoundsBenzene and substituted derivativesDialkylaminesHydrocarbon derivativesOrganopnictogen compoundsTetrahydroisoquinolines1-hydroxy-2-unsubstituted benzenoidAlkyl aryl etherAmineAnisoleAralkylamineAromatic heteropolycyclic compoundAzacycleBenzenoidBenzylisoquinolineEtherHydrocarbon derivativeMonocyclic benzene moietyOrganic nitrogen compoundOrganic oxygen compoundOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhenolSecondary aliphatic amineSecondary amineTetrahydroisoquinolinecoclaurinelogp2.20logs-3.37solubility1.23e-01 g/lmelting_pointMp 217-218°logp2.51pka_strongest_acidic9.92pka_strongest_basic8.91iupac1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-olaverage_mass285.3377mono_mass285.136493479smilesCOC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2formulaC17H19NO3inchiInChI=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,6-8H2,1H3inchikeyLVVKXRQZSRUVPY-UHFFFAOYSA-Npolar_surface_area61.72refractivity82.08polarizability31.31rotatable_bond_count3acceptor_count4donor_count3physiological_charge1formal_charge0Specdb::MsMs21203Specdb::MsMs21204Specdb::MsMs21205Specdb::MsMs22754Specdb::MsMs22755Specdb::MsMs22756Specdb::MsMs3605275Specdb::MsMs3605276Specdb::MsMs3605277Specdb::MsMs3605278Specdb::MsMs3605279Specdb::MsMs360528018417Custard appleType 1specificAnnona reticulata301862SoursopType 1specificAnnona muricata13337anti aggregant94anti radicular572antioxidant502A 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.cytotoxic859A role played by the molecular entity or part thereof which causes the development of a pathological process.depressant872hypothermic1023