{"ymdb_id":"YMDB00498","created_at":"2011-05-29T18:23:52.000Z","updated_at":"2016-09-08T18:35:32.000Z","name":"trans-4-Coumaric acid","cas":"501-98-4","state":"Solid","melting_point":"211.5 oC","description":"p-Coumaric acid is a hydroxycinnamic acid related to cinnamic acid, a type of polyphenol. It is an abundant phenolic phytochemical found in plant cell wall components. It is present in beer and wine. p-Coumaric acid is decarboxylated to 4-vinylphenol during wine fermentation by phenyl acrylic acid decarboxylase of certain strains yeast. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. [PMID: 17303275]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":"1.79 [SANGSTER (1994)]","location":"Mitochondrion","synthesis_reference":"Ben-Bassat, Arie; Sariaslani, Fateme Sima; Huang, Lisa L.; Patnaik, Ranjan; Lowe, David J.  Fermentative preparation of para-hydroxycinnamic acid and cinnamic acid at alkaline ph.    U.S. Pat. Appl. Publ.  (2005),     23 pp. ","chebi_id":"32374","hmdb_id":"HMDB02035","kegg_id":"C00811","pubchem_id":"322","cs_id":null,"foodb_id":null,"wikipedia_link":"Coumaric_acid","biocyc_id":"COUMARATE","iupac":"(2E)-3-(4-hydroxyphenyl)prop-2-enoic acid","traditional_iupac":"coumaric acid","logp":"1.832520938333333","pka":"9.514998441470318","alogps_solubility":"1.02e+00 g/l","alogps_logp":"1.74","alogps_logs":"-2.21","acceptor_count":"3","donor_count":"2","rotatable_bond_count":"2","polar_surface_area":"57.53","refractivity":"45.040800000000004","polarizability":"16.431899091719323","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"-5.954717586543567","pka_strongest_acidic":"4.002242567462163","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"1","veber_rule":"0","mddr_like_rule":"0","synonyms":[".beta.-[4-Hydroxyphenyl]acrylic acid","(2E)-3-(4-Hydroxyphenyl)-2-propenoic acid","(2E)-3-(4-hydroxyphenyl)acrylate","(2E)-3-(4-hydroxyphenyl)acrylic acid","(E)-3-(4-hydroxyphenyl)-2-propenoic acid","(E)-p-coumaric acid","(E)-p-hydroxycinnamic acid","2-Propenoic acid, 3-(4-hydroxyphenyl)-","2-Propenoic acid, 3-(4-hydroxyphenyl)-, (2E)-","2-Propenoic acid, 3-(4-hydroxyphenyl)-, (E)-","3-(4-Hydroxyphenyl)-2-propenoate","3-(4-Hydroxyphenyl)-2-propenoic acid","3-(4-hydroxyphenyl)acrylate","3-(4-hydroxyphenyl)acrylic acid","4 - hydroxycinnamic acid","4-coumarate","4-Coumaric acid","4-Hydroxy cinnamate","4-Hydroxy cinnamic acid","4-hydroxycinnamate","4-hydroxycinnamic acid","4-Hydroxyphenylpropenoate","4-Hydroxyphenylpropenoic acid","4'-Hydroxycinnamate","4'-Hydroxycinnamic acid","b-[4-Hydroxyphenyl]acrylate","b-[4-Hydroxyphenyl]acrylic acid","beta-[4-Hydroxyphenyl]acrylate","beta-[4-Hydroxyphenyl]acrylic acid","Cinnamic acid, p-hydroxy-","Cinnamic acid, p-hydroxy-, (E)-","cis-p-Coumarate","hydroxycinnamate","hydroxycinnamic acid","naringeninic acid","p-Coumarate","p-coumaric acid","p-Coumaric acid,trans","p-Cumarate","p-Cumaric acid","p-Hydroxycinnamate","p-Hydroxycinnamic acid","p-Hydroxyphenylacrylate","p-Hydroxyphenylacrylic acid","Para coumarate","Para coumaric acid","Para-Coumarate","Para-Coumaric acid","trans-4-Hydroxycinnamate","trans-4-Hydroxycinnamic acid","trans-p-coumarate","trans-p-coumaric acid","trans-p-coumarinic acid","trans-p-Hydroxycinnamate","trans-p-hydroxycinnamic acid"],"pathways":[{"name":"Phenylalanine metabolism","kegg_map_id":"00360"},{"name":"Ubiquinone and other terpenoid-quinone biosynthesis","kegg_map_id":"00130"}],"growth_conditions":[],"references":[{"pubmed_id":18846089,"citation":"Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). \"A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology.\" Nat Biotechnol 26:1155-1160."}],"proteins":[]}