1.0 2011-09-21 00:23:21 UTC 2019-11-26 03:21:07 UTC FDB023019 3,4,5-Trimethoxycinnamic acid 3,4,5-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] 3,4,5-Trimethoxy cinnamate 3,4,5-Trimethoxy cinnamic acid 3,4,5-Trimethoxycinnamate 3,4,5-Trimethoxyphenylacrylate 3,4,5-Trimethoxyphenylacrylic acid O-Methylsinapate O-Methylsinapic acid C12H14O5 238.2366 238.084123558 (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid 3,4,5-trimethoxycinnamic acid 90-50-6 COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+ YTFVRYKNXDADBI-SNAWJCMRSA-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 2.24 ALOGPS logs -3.05 ALOGPS solubility 2.12e-01 g/l ALOGPS logp 1.66 ChemAxon pka_strongest_acidic 3.71 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac (2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoic acid ChemAxon average_mass 238.2366 ChemAxon mono_mass 238.084123558 ChemAxon smiles COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC ChemAxon formula C12H14O5 ChemAxon inchi InChI=1S/C12H14O5/c1-15-9-6-8(4-5-11(13)14)7-10(16-2)12(9)17-3/h4-7H,1-3H3,(H,13,14)/b5-4+ ChemAxon inchikey YTFVRYKNXDADBI-SNAWJCMRSA-N ChemAxon polar_surface_area 64.99 ChemAxon refractivity 62.45 ChemAxon polarizability 24.17 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 5 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1830 Specdb::CMs 1529 Specdb::CMs 23887 Specdb::CMs 29827 Specdb::CMs 31420 Specdb::CMs 38434 Specdb::CMs 164916 Specdb::NmrOneD 1894 Specdb::NmrOneD 166623 Specdb::MsMs 2113 Specdb::MsMs 2114 Specdb::MsMs 2115 Specdb::MsMs 318928 Specdb::MsMs 318929 Specdb::MsMs 318930 Specdb::MsMs 365872 Specdb::MsMs 365873 Specdb::MsMs 365874 Specdb::MsMs 374866 Specdb::MsMs 439792 Specdb::MsMs 439793 Specdb::MsMs 445423 Specdb::MsMs 445424 Specdb::MsMs 445425 Specdb::MsMs 447427 Specdb::MsMs 447428 Specdb::MsMs 447429 Specdb::MsMs 447430 Specdb::MsMs 449966 Specdb::MsMs 449967 Specdb::MsMs 449968 Specdb::MsMs 449969 Specdb::MsMs 451591 Specdb::MsMs 452053 HMDB02511 #<Reference:0x000055ce31aad200> #<Reference:0x000055ce31aad048> #<Reference:0x000055ce31aace90> #<Reference:0x000055ce31aaccd8> 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 Milk (Cow) Type 2 specific 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