{"ymdb_id":"YMDB01624","created_at":"2011-08-31T03:29:26.000Z","updated_at":"2016-09-08T18:36:54.000Z","name":"4-Vinylguaiacol","cas":"7786-61-0","state":null,"melting_point":null,"description":"4-Vinylguaiacol is a vinylphenol, a type of pyranoanthocyanin. 4-Vinylguaiacol is produced by enzymatic decarboxylation of the grape compound ferulic acid by certain strains of S. cerevisiae. Vinylphenols then spontaneously condensate with grape anthocyanins (mainly malvidin-3-O-glucoside) to form pigments important for the color of ageing wine. 4-Vinylguaiacol is also found in beers and is responsible for a pungent clove-like aroma. [PMID: 17303275]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":null,"synthesis_reference":null,"chebi_id":null,"hmdb_id":null,"kegg_id":"C17883","pubchem_id":"332","cs_id":"325","foodb_id":null,"wikipedia_link":null,"biocyc_id":null,"iupac":"4-ethenyl-2-methoxyphenol","traditional_iupac":"2-methoxy-4-vinyl-phenol","logp":"2.2487112966666665","pka":null,"alogps_solubility":"7.42e+00 g/l","alogps_logp":"1.84","alogps_logs":"-1.31","acceptor_count":"2","donor_count":"1","rotatable_bond_count":"2","polar_surface_area":"29.46","refractivity":"44.18840000000001","polarizability":"15.98631844617077","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"-4.89373168768089","pka_strongest_acidic":"10.034622277956638","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"1","mddr_like_rule":"0","synonyms":["2-methoxy-4-vinylphenol (4-vinylguaiacol)","2-methoxy-4-vinylphenol (vinylguaiacol)","2-Methoxy-vinylphenol","2-metoxy-4-vinyl-phenol","4-ethenyl-2-methoxyphenol","4-Hydroxy-3-methoxystyrene","4-Vinyl-2-methoxyphenol","4-vinyl-2-methoxyphenol ( p-vinylguaiacol)","4-Vinyl-2-methoxyphenol (4-vinylguaiacol)","4-Vinylguaiacol","4-Vinylguaiacole","guaiacol, 4-vinyl","o-methoxy-p-vinylphenol","p-Vinyl guaicol","p-Vinylguaiacol","para-vinylguaiacol","Phenol, 2-methoxy-4-ethenyl","Phenol, 2-methoxy-4-vinyl-","Phenol, 4-ethenyl-2-methoxy-","Phenol, 4-vinyl, 2-methoxy","vinylguaiacol (4-vinyl-2-methoxyphenol)"],"pathways":[{"name":"Beer Reactions","kegg_map_id":null}],"growth_conditions":[],"references":[{"pubmed_id":null,"citation":"McMurrough, I., Madigan, D., Donelly, D., Hurley, J.,Doyle, AM., Heenigan, G., McNulty, N. and Smyth, MR. (1996) \"Control of Ferulic Acid and 4-Vinyl Guaicol in Brewing.\" Journal of the Institute of Brewing 102:5, pg 327-332"},{"pubmed_id":17616208,"citation":"Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). \"Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions.\" J Agric Food Chem 55:6674-6684."}],"proteins":[{"created_at":"2016-09-09T22:49:02.000Z","updated_at":"2016-09-09T22:49:03.000Z","name":"Ferulic acid decarboxylase 1","uniprot_id":"Q03034","uniprot_name":"FDC1","enzyme":true,"transporter":false,"gene_name":"FDC1","num_residues":503,"molecular_weight":"56163.39","theoretical_pi":null,"general_function":"ferulate metabolic process","specific_function":"Catalyzes the reversible decarboxylation of aromatic carboxylic acids like ferulic acid, p-coumaric acid or cinnamic acid, producing the corresponding vinyl derivatives 4-vinylphenol, 4-vinylguaiacol, and styrene, respectively, which play the role of aroma metabolites (PubMed:20471595, PubMed:25647642). Not essential for ubiquinone synthesis (PubMed:20471595).","reactions":[{"id":34376,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R007484","source":"Smpdb"}],"signal_regions":null,"transmembrane_regions":null,"pdb_id":"4S13","cellular_location":null,"genbank_gene_id":null,"genbank_protein_id":null,"gene_card_id":null,"chromosome_location":null,"locus":null,"synonyms":["Phenacrylate decarboxylase"],"enzyme_classes":[],"go_classes":[{"category":"Function","description":"metal ion binding"},{"category":"Function","description":"oxidoreductase activity"},{"category":"Function","description":"cytoplasm"},{"category":"Function","description":"carboxy-lyase activity"},{"category":"Function","description":"FMN binding"},{"category":"Function","description":"cinnamic acid catabolic process"},{"category":"Function","description":"ferulate metabolic process"}],"pfams":[],"pathways":[{"name":"Beer Reactions","kegg_map_id":null}],"gene_sequence":"ATGAGGAAGCTAAATCCAGCTTTAGAATTTAGAGACTTTATCCAGGTCTTAAAAGATGAAGATGACTTAATCGAAATTACCGAAGAGATTGATCCAAATCTCGAAGTAGGTGCAATTATGAGGAAGGCCTATGAATCCCACTTACCAGCCCCGTTATTTAAAAATCTCAAAGGTGCTTCGAAGGATCTTTTCAGCATTTTAGGTTGCCCAGCCGGTTTGAGAAGTAAGGAGAAAGGAGATCATGGTAGAATTGCCCATCATCTGGGGCTCGACCCAAAAACAACTATCAAGGAAATCATAGATTATTTGCTGGAGTGTAAGGAGAAGGAACCTCTCCCCCCAATCACTGTTCCTGTGTCATCTGCACCTTGTAAAACACATATACTTTCTGAAGAAAAAATACATCTACAAAGCCTGCCAACACCATATCTACATGTTTCAGACGGTGGCAAGTACTTACAAACGTACGGAATGTGGATTCTTCAAACTCCAGATAAAAAATGGACTAATTGGTCAATTGCTAGAGGTATGGTTGTAGATGACAAGCATATCACTGGTCTGGTAATTAAACCACAACATATTAGACAAATTGCTGACTCTTGGGCAGCAATTGGAAAAGCAAATGAAATTCCTTTCGCGTTATGTTTTGGCGTTCCCCCAGCAGCTATTTTAGTTAGTTCCATGCCAATTCCTGAAGGTGTTTCTGAATCGGATTATGTTGGCGCAATCTTGGGTGAGTCGGTTCCAGTAGTAAAATGTGAGACCAACGATTTAATGGTTCCTGCAACGAGTGAGATGGTATTTGAGGGTACTTTGTCCTTAACAGATACACATCTGGAAGGCCCATTTGGTGAGATGCATGGATATGTTTTCAAAAGCCAAGGTCATCCTTGTCCATTGTACACTGTCAAGGCTATGAGTTACAGAGACAATGCTATTCTACCTGTTTCGAACCCCGGTCTTTGTACGGATGAGACACATACCTTGATTGGTTCACTAGTGGCTACTGAGGCCAAGGAGCTGGCTATTGAATCTGGCTTGCCAATTCTGGATGCCTTTATGCCTTATGAGGCTCAGGCTCTTTGGCTTATCTTAAAGGTGGATTTGAAAGGGCTGCAAGCATTGAAGACAACGCCTGAAGAATTTTGTAAGAAGGTAGGTGATATTTACTTTAGGACAAAAGTTGGTTTTATAGTCCATGAAATAATTTTGGTGGCAGATGATATCGACATATTTAACTTCAAAGAAGTCATCTGGGCCTACGTTACAAGACATACACCTGTTGCAGATCAGATGGCTTTTGATGATGTCACTTCTTTTCCTTTGGCTCCCTTTGTTTCGCAGTCATCCAGAAGTAAGACTATGAAAGGTGGAAAGTGCGTTACTAATTGCATATTTAGACAGCAATATGAGCGCAGTTTTGACTACATAACTTGTAATTTTGAAAAGGGATATCCAAAAGGATTAGTTGACAAAGTAAATGAAAATTGGAAAAGGTACGGATATAAATAA","protein_sequence":"MRKLNPALEFRDFIQVLKDEDDLIEITEEIDPNLEVGAIMRKAYESHLPAPLFKNLKGASKDLFSILGCPAGLRSKEKGDHGRIAHHLGLDPKTTIKEIIDYLLECKEKEPLPPITVPVSSAPCKTHILSEEKIHLQSLPTPYLHVSDGGKYLQTYGMWILQTPDKKWTNWSIARGMVVDDKHITGLVIKPQHIRQIADSWAAIGKANEIPFALCFGVPPAAILVSSMPIPEGVSESDYVGAILGESVPVVKCETNDLMVPATSEMVFEGTLSLTDTHLEGPFGEMHGYVFKSQGHPCPLYTVKAMSYRDNAILPVSNPGLCTDETHTLIGSLVATEAKELAIESGLPILDAFMPYEAQALWLILKVDLKGLQALKTTPEEFCKKVGDIYFRTKVGFIVHEIILVADDIDIFNFKEVIWAYVTRHTPVADQMAFDDVTSFPLAPFVSQSSRSKTMKGGKCVTNCIFRQQYERSFDYITCNFEKGYPKGLVDKVNENWKRYGYK"}]}