1.0 2010-04-08 22:07:01 UTC 2025-11-18 23:01:06 UTC FDB006174 Lithospermic acid Lithospermic acid, also known as lithospermate, is a member of the class of compounds known as 2-arylbenzofuran flavonoids. 2-arylbenzofuran flavonoids are phenylpropanoids containing the 2-phenylbenzofuran moiety. Lithospermic acid is practically insoluble (in water) and a moderately acidic compound (based on its pKa). Lithospermic acid can be found in common thyme and peppermint, which makes lithospermic acid a potential biomarker for the consumption of these food products. C27H22O12 538.4564 538.111126168 4-[(1Z)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid 4-[(1Z)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid OC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)\C=C/C1=C2C(C(OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4- UJZQBMQZMKFSRV-YWEYNIOJSA-N belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. 2-arylbenzofuran flavonoids Organic compounds Phenylpropanoids and polyketides 2-arylbenzofuran flavonoids Aromatic heteropolycyclic compounds 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Carbonyl compounds Carboxylic acids Catechols Coumarans Coumaric acids and derivatives Enoate esters Fatty acid esters Hydrocarbon derivatives Organic oxides Oxacyclic compounds Phenylpropanoic acids Styrenes Tricarboxylic acids and derivatives 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-arylbenzofuran flavonoid 3-phenylpropanoic-acid Alkyl aryl ether Alpha,beta-unsaturated carboxylic ester Aromatic heteropolycyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Catechol Coumaran Coumaric acid or derivatives Enoate ester Ether Fatty acid ester Fatty acyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Styrene Tricarboxylic acid or derivatives logp 3.58 ALOGPS logs -4.41 ALOGPS solubility 2.10e-02 g/l ALOGPS logp 3.75 ChemAxon pka_strongest_acidic 2.89 ChemAxon pka_strongest_basic -5.1 ChemAxon iupac 4-[(1Z)-3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-en-1-yl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid ChemAxon average_mass 538.4564 ChemAxon mono_mass 538.111126168 ChemAxon smiles OC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)\C=C/C1=C2C(C(OC2=C(O)C=C1)C1=CC=C(O)C(O)=C1)C(O)=O ChemAxon formula C27H22O12 ChemAxon inchi InChI=1S/C27H22O12/c28-15-5-1-12(9-18(15)31)10-20(26(34)35)38-21(33)8-4-13-2-7-17(30)25-22(13)23(27(36)37)24(39-25)14-3-6-16(29)19(32)11-14/h1-9,11,20,23-24,28-32H,10H2,(H,34,35)(H,36,37)/b8-4- ChemAxon inchikey UJZQBMQZMKFSRV-YWEYNIOJSA-N ChemAxon polar_surface_area 211.28 ChemAxon refractivity 133.07 ChemAxon polarizability 50.14 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 11 ChemAxon donor_count 7 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 88293 Specdb::MsMs 88294 Specdb::MsMs 88295 Specdb::MsMs 150990 Specdb::MsMs 150991 Specdb::MsMs 150992 Common thyme Type 1 specific Thymus vulgaris 49992 Peppermint Type 1 specific Mentha X piperita 34256 Anti gonadotrophic 307 Anti-thyroid 654 Cardiotonic 771 A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.