1.0 2010-04-08 22:09:50 UTC 2025-11-18 23:31:15 UTC FDB011812 Coclaurine Coclaurine, 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)-Coclaurine Coclaurine D-coclaurine Machiline Sanjoinine K C17H19NO3 285.3377 285.136493479 1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol (RS)-coclaurine 2196-60-3 COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2 InChI=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 LVVKXRQZSRUVPY-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. Benzylisoquinolines Organic compounds Organoheterocyclic compounds Isoquinolines and derivatives Benzylisoquinolines Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Anisoles Aralkylamines Azacyclic compounds Benzene and substituted derivatives Dialkylamines Hydrocarbon derivatives Organopnictogen compounds Tetrahydroisoquinolines 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Amine Anisole Aralkylamine Aromatic heteropolycyclic compound Azacycle Benzenoid Benzylisoquinoline Ether Hydrocarbon derivative Monocyclic benzene moiety Organic nitrogen compound Organic oxygen compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Secondary aliphatic amine Secondary amine Tetrahydroisoquinoline coclaurine logp 2.20 ALOGPS logs -3.37 ALOGPS solubility 1.23e-01 g/l ALOGPS melting_point Mp 217-218° logp 2.51 ChemAxon pka_strongest_acidic 9.92 ChemAxon pka_strongest_basic 8.91 ChemAxon iupac 1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol ChemAxon average_mass 285.3377 ChemAxon mono_mass 285.136493479 ChemAxon smiles COC1=CC2=C(C=C1O)C(CC1=CC=C(O)C=C1)NCC2 ChemAxon formula C17H19NO3 ChemAxon inchi InChI=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 ChemAxon inchikey LVVKXRQZSRUVPY-UHFFFAOYSA-N ChemAxon polar_surface_area 61.72 ChemAxon refractivity 82.08 ChemAxon polarizability 31.31 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 4 ChemAxon donor_count 3 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 21203 Specdb::MsMs 21204 Specdb::MsMs 21205 Specdb::MsMs 22754 Specdb::MsMs 22755 Specdb::MsMs 22756 Specdb::MsMs 3605275 Specdb::MsMs 3605276 Specdb::MsMs 3605277 Specdb::MsMs 3605278 Specdb::MsMs 3605279 Specdb::MsMs 3605280 18417 Custard apple Type 1 specific Annona reticulata 301862 Soursop Type 1 specific Annona muricata 13337 Anti radicular 572 Anti-aggregant 94 Anti-oxidant 502 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. Cytotoxic 859 A role played by the molecular entity or part thereof which causes the development of a pathological process. Depressant 872 Hypothermic 1023