1.0 2010-04-08 22:05:15 UTC 2019-11-26 02:57:05 UTC FDB002151 Thesinine Thesinine is a member of the class of compounds known as coumaric acid esters. Coumaric acid esters are aromatic compounds containing an ester derivative of coumaric acid. Thesinine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Thesinine can be found in borage, which makes thesinine a potential biomarker for the consumption of this food product. Thesinine is a pyrrolizidine alkaloid first isolated from Thesium minkwitzianum from which it derives its name. It is also found in the flowers and seeds of borage . (-)-thesinine Thesinine C17H21NO3 287.3535 287.152143543 hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate 488-02-8 OC1=CC=C(\C=C\C(=O)OCC2CCN3CCCC23)C=C1 InChI=1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+ FQVNMXZPGWLUFZ-VMPITWQZSA-N belongs to the class of organic compounds known as coumaric acid esters. These are aromatic compounds containing an ester derivative of coumaric acid. Coumaric acid esters Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids Amino acids and derivatives Azacyclic compounds Carbonyl compounds Cinnamic acid esters Coumaric acids and derivatives Enoate esters Fatty acid esters Hydrocarbon derivatives Monocarboxylic acids and derivatives N-alkylpyrrolidines Organic oxides Organopnictogen compounds Pyrrolizidines Styrenes Trialkylamines 1-hydroxy-2-unsubstituted benzenoid Alpha,beta-unsaturated carboxylic ester Amine Amino acid or derivatives Aromatic heteropolycyclic compound Azacycle Benzenoid Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cinnamic acid ester Coumaric acid ester Coumaric acid or derivatives Enoate ester Fatty acid ester Fatty acyl Hydrocarbon derivative Monocarboxylic acid or derivatives Monocyclic benzene moiety N-alkylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Phenol Pyrrolidine Pyrrolizidine Styrene Tertiary aliphatic amine Tertiary amine logp 2.30 ALOGPS logs -2.70 ALOGPS solubility 5.76e-01 g/l ALOGPS melting_point Mp 38-40° logp 1.74 ChemAxon pka_strongest_acidic 9.34 ChemAxon pka_strongest_basic 10.29 ChemAxon iupac hexahydro-1H-pyrrolizin-1-ylmethyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate ChemAxon average_mass 287.3535 ChemAxon mono_mass 287.152143543 ChemAxon smiles OC1=CC=C(\C=C\C(=O)OCC2CCN3CCCC23)C=C1 ChemAxon formula C17H21NO3 ChemAxon inchi InChI=1S/C17H21NO3/c19-15-6-3-13(4-7-15)5-8-17(20)21-12-14-9-11-18-10-1-2-16(14)18/h3-8,14,16,19H,1-2,9-12H2/b8-5+ ChemAxon inchikey FQVNMXZPGWLUFZ-VMPITWQZSA-N ChemAxon polar_surface_area 49.77 ChemAxon refractivity 82.59 ChemAxon polarizability 32.15 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 87987 Specdb::MsMs 87988 Specdb::MsMs 87989 Specdb::MsMs 150615 Specdb::MsMs 150616 Specdb::MsMs 150617 Specdb::MsMs 3599056 Specdb::MsMs 3599057 Specdb::MsMs 3599058 Specdb::MsMs 3599059 Specdb::MsMs 3599060 Specdb::MsMs 3599061 Borage Type 1 specific Borago officinalis 13363 20.0 20.0 20.0 mg/100 g