1.0 2011-09-21 01:39:16 UTC 2015-07-21 06:59:24 UTC FDB028405 trans-2,3,4-Trimethoxycinnamate Trimethoxycinnamic acid is an organic acid found in normal human urine. (PMID: 6992730, 6511847) Trimethoxycinnamate is a natural aromatic ester from Piper longum that inhibits expression of cell adhesion molecules on endothelial cells (TNF- -induced expression of intercellular adhesion molecule-1 (ICAM-1) and E-Selectin and vascular adhesion molecules-1 (VCAM-1)), without being toxic to endothelial cells. (PMID: 16313198) [HMDB] (2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoate (2E)-3-(2,3,4-Trimethoxyphenyl)-2-propenoic acid 3-(2,3,4-trimethoxyphenyl)-2-Propenoate 3-(2,3,4-trimethoxyphenyl)-2-Propenoic acid C12H14O5 238.2366 238.084123558 (2E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid (2E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid 33130-03-9 COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+ ZYOPDNLIHHFGEC-FNORWQNLSA-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. Coumaric acids and derivatives Organic compounds Phenylpropanoids and polyketides Cinnamic acids and derivatives Hydroxycinnamic acids and derivatives Aromatic homomonocyclic compounds Alkyl aryl ethers Anisoles Carbonyl compounds Carboxylic acids Cinnamic acids Hydrocarbon derivatives Methoxybenzenes Monocarboxylic acids and derivatives Organic oxides Phenoxy compounds Styrenes Alkyl aryl ether Anisole Aromatic homomonocyclic compound Benzenoid Carbonyl group Carboxylic acid Carboxylic acid derivative Cinnamic acid Coumaric acid or derivatives Ether Hydrocarbon derivative Methoxybenzene Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organooxygen compound Phenol ether Phenoxy compound Styrene Solid logp 2.23 ALOGPS logs -3.03 ALOGPS solubility 2.24e-01 g/l ALOGPS logp 1.66 ChemAxon pka_strongest_acidic 3.72 ChemAxon pka_strongest_basic -4.5 ChemAxon iupac (2E)-3-(2,3,4-trimethoxyphenyl)prop-2-enoic acid ChemAxon average_mass 238.2366 ChemAxon mono_mass 238.084123558 ChemAxon smiles COC1=CC=C(\C=C\C(O)=O)C(OC)=C1OC ChemAxon formula C12H14O5 ChemAxon inchi InChI=1S/C12H14O5/c1-15-9-6-4-8(5-7-10(13)14)11(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b7-5+ ChemAxon inchikey ZYOPDNLIHHFGEC-FNORWQNLSA-N ChemAxon polar_surface_area 64.99 ChemAxon refractivity 62.45 ChemAxon polarizability 24.16 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 17242 Specdb::CMs 39775 Specdb::CMs 133285 Specdb::CMs 141019 Specdb::MsMs 304126 Specdb::MsMs 304127 Specdb::MsMs 304128 Specdb::MsMs 347242 Specdb::MsMs 347243 Specdb::MsMs 347244 Specdb::MsMs 2289588 Specdb::MsMs 2289589 Specdb::MsMs 2289590 Specdb::MsMs 2648664 Specdb::MsMs 2648665 Specdb::MsMs 2648666 HMDB11721 #<Reference:0x000055ce31868f80> #<Reference:0x000055ce31868dc8> #<Reference:0x000055ce31868be8> #<Reference:0x000055ce31868a30> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823