1.0 2016-09-30 23:05:23 UTC 2020-05-11 20:03:12 UTC BMDB0003572 BMDB03572 Rosmarinic acid (2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactic acid (2R)-O-Caffeoyl-3-(3,4-dihydroxyphenyl)lactate Rosmarinate Rosemary acid Rosmarinic acid, (R-(e))-isomer (R)-Rosmarinate Labiatenic acid Labiatic acid Rosemaric acid trans-Rosmarinic acid (Z)-Rosmarinic acid Rosmarinic acid C18H16O8 360.3148 360.084517488 (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid rosemary acid 20283-92-5 OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1 InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1 DOUMFZQKYFQNTF-WUTVXBCWSA-N belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Coumaric acids and derivatives 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Carbonyl compounds Carboxylic acids Catechols Cinnamic acid esters Dicarboxylic acids and derivatives Enoate esters Fatty acid esters Hydrocarbon derivatives Organic oxides Phenylpropanoic acids Styrenes 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 3-phenylpropanoic-acid Alpha,beta-unsaturated carboxylic ester Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Catechol Cinnamic acid ester Coumaric acid or derivatives Dicarboxylic acid or derivatives Enoate ester Fatty acid ester Fatty acyl Hydrocarbon derivative Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol Styrene Aromatic homomonocyclic compounds rosmarinic acid Solid logp 2.57 ALOGPS logs -3.95 ALOGPS logp 3 ChemAxon pka_strongest_acidic 3.13 ChemAxon pka_strongest_basic -6.3 ChemAxon iupac (2R)-3-(3,4-dihydroxyphenyl)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}propanoic acid ChemAxon average_mass 360.3148 ChemAxon mono_mass 360.084517488 ChemAxon smiles OC(=O)[C@@H](CC1=CC(O)=C(O)C=C1)OC(=O)\C=C\C1=CC(O)=C(O)C=C1 ChemAxon formula C18H16O8 ChemAxon inchi InChI=1S/C18H16O8/c19-12-4-1-10(7-14(12)21)3-6-17(23)26-16(18(24)25)9-11-2-5-13(20)15(22)8-11/h1-8,16,19-22H,9H2,(H,24,25)/b6-3+/t16-/m1/s1 ChemAxon inchikey DOUMFZQKYFQNTF-WUTVXBCWSA-N ChemAxon polar_surface_area 144.52 ChemAxon refractivity 90.95 ChemAxon polarizability 34.55 ChemAxon rotatable_bond_count 7 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 2 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::CMs 2308 Specdb::CMs 23013 Specdb::CMs 31469 Specdb::CMs 38632 Specdb::CMs 156187 Specdb::MsMs 109956 Specdb::MsMs 109957 Specdb::MsMs 109958 Specdb::MsMs 177510 Specdb::MsMs 177511 Specdb::MsMs 177512 Specdb::MsMs 438992 Specdb::MsMs 438993 Specdb::MsMs 438994 Specdb::MsMs 438995 Specdb::MsMs 439157 Specdb::MsMs 447887 Specdb::MsMs 447888 Specdb::MsMs 447889 Specdb::MsMs 452021 Specdb::MsMs 452022 Specdb::MsMs 2241115 Specdb::MsMs 2244788 Specdb::MsMs 2245341 Specdb::MsMs 2246822 Specdb::MsMs 2247450 Specdb::MsMs 2248831 Specdb::MsMs 2249569 Specdb::MsMs 2250875 Specdb::MsMs 2251519 Fibroblasts Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 FDB002427 4445104 461 C01850 5281792 50371 CPD-6981 Rosmarinic_acid C00002770 6960