{"ymdb_id":"YMDB00495","created_at":"2011-05-29T18:23:29.000Z","updated_at":"2016-09-08T18:35:32.000Z","name":"4-Hydroxybenzoic acid","cas":"99-96-7","state":"Solid","melting_point":"214.5 oC","description":"4-Hydroxybenzoic acid is a phenolic acid, a type of polyphenol. Polyphenol are secondary plant metabolites and component of grapes and wines that contribute to the sensory characteristics of wine. Yeast can influence the polyphenolic wine composition by adsorbing them throught its cell wall during wine making. [Caridi 2004]","experimental_water_solubility":"5 mg/mL at 25 oC [YALKOWSKY,SH \u0026 DANNENFELSER,RM (1992)]","experimental_logp_hydrophobicity":"1.58 [HANSCH,C ET AL. (1995)]","location":"Cytoplasm;Mitochondrion","synthesis_reference":"Ivanov, G. E.; Slavcheva, L.  Preparation, properties, and applications of p-hydroxy-benzoic acid.    Khimiya i Industriya (1922-1988)  (1966),  38(10),  458-63. ","chebi_id":"30763","hmdb_id":"HMDB00500","kegg_id":"C00156","pubchem_id":"135","cs_id":"132","foodb_id":null,"wikipedia_link":"4-Hydroxybenzoic_acid","biocyc_id":"4-hydroxybenzoate","iupac":"4-hydroxybenzoic acid","traditional_iupac":"P-hydroxybenzoic acid","logp":"1.3272634023333332","pka":"9.67428543984855","alogps_solubility":"1.19e+01 g/l","alogps_logp":"1.58","alogps_logs":"-1.06","acceptor_count":"3","donor_count":"2","rotatable_bond_count":"1","polar_surface_area":"57.53","refractivity":"35.2951","polarizability":"12.939727468110942","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"-6.063011046171021","pka_strongest_acidic":"4.379964053135935","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["4-Carboxyphenol","4-hydroxy-benzoate","4-Hydroxy-benzoesaeure","4-hydroxy-benzoic acid","4-Hydroxybenzoate","4-Hydroxybenzoic acid","4-hydroxybenzoic acid, ion(1-)","Benzoic acid, 4-hydroxy","Benzoic acid, 4-hydroxy-","Benzoic acid, p-hydroxy","Benzoic acid, p-hydroxy-","hydroxybenzenecarboxylic acid","hydroxybenzoic acid","Hydroxybenzoic acid, para","Kyselina 4-hydroxybenzoova","p-Carboxyphenol","p-hydroxy-Benzoate","p-hydroxy-Benzoic acid","p-Hydroxybenzoate","p-Hydroxybenzoic acid","p-Salicylate","p-Salicylic acid","para-Hydroxybenzoic acid","Paraben","Paraben-acid","Viminol 4-hydroxybenzoate"],"pathways":[{"name":"Phenylalanine metabolism","kegg_map_id":"00360"},{"name":"Ubiquinone and other terpenoid-quinone biosynthesis","kegg_map_id":"00130"},{"name":"Ubiquinone Biosynthesis","kegg_map_id":null}],"growth_conditions":[],"references":[{"pubmed_id":21062828,"citation":"Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). \"BRENDA, the enzyme information system in 2011.\" Nucleic Acids Res 39:D670-D676."},{"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."},{"pubmed_id":10760477,"citation":"Hsu, A. Y., Do, T. Q., Lee, P. T., Clarke, C. F. (2000). \"Genetic evidence for a multi-subunit complex in the O-methyltransferase steps of coenzyme Q biosynthesis.\" Biochim Biophys Acta 1484:287-297."},{"pubmed_id":1763050,"citation":"He, B., Chen, P., Chen, S. Y., Vancura, K. L., Michaelis, S., Powers, S. (1991). \"RAM2, an essential gene of yeast, and RAM1 encode the two polypeptide components of the farnesyltransferase that prenylates a-factor and Ras proteins.\" Proc Natl Acad Sci U S A 88:11373-11377."}],"proteins":[{"created_at":"2011-05-27T04:24:08.000Z","updated_at":"2011-05-29T05:06:41.000Z","name":"Para-hydroxybenzoate--polyprenyltransferase, mitochondrial","uniprot_id":"P32378","uniprot_name":"COQ2_YEAST","enzyme":true,"transporter":false,"gene_name":"COQ2","num_residues":372,"molecular_weight":"41001.0","theoretical_pi":"10.47","general_function":"Involved in prenyltransferase activity","specific_function":"Catalyzes the prenylation of para-hydroxybenzoate (PHB) with an all-trans polyprenyl group. Mediates the second step in the final reaction sequence of coenzyme Q (CoQ) biosynthesis, which is the condensation of the polyisoprenoid side chain with PHB","reactions":[{"id":1645,"direction":"\u003e","locations":"mitochondrion","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2764,"direction":"\u003e","locations":"Mitochondrion inner membrane; Multi-pass membrane protein","altext":"A polyprenyl diphosphate + 4-hydroxybenzoate = diphosphate + a 4-hydroxy-3-polyprenylbenzoate.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"92-112;114-133;170-191;193-210;229-249;298-318","pdb_id":null,"cellular_location":"Mitochondrion inner membrane; Multi-pass membrane protein","genbank_gene_id":"AY693097","genbank_protein_id":"51013645","gene_card_id":"COQ2","chromosome_location":"chromosome 14","locus":"YNR041C","synonyms":["PHB:polyprenyltransferase"],"enzyme_classes":["2.5.1.39"],"go_classes":[{"category":"Component","description":" cell part"},{"category":"Component","description":" membrane part"},{"category":"Component","description":" intrinsic to membrane"},{"category":"Component","description":" integral to membrane"},{"category":"Function","description":" prenyltransferase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring alkyl or aryl (other than methyl) groups"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" biosynthetic process"}],"pfams":[{"name":"UbiA","identifier":"PF01040"}],"pathways":[],"gene_sequence":"ATGTTTATTTGGCAGAGAAAGAGTATTTTACTAGGGAGGTCCATTCTGGGCAGCGGCCGAGTTACCGTTGCTGGAATCATTGGAAGCAGCAGAAAGAGATATACGTCTTCTTCCTCCTCCTCCTCCTCCCCTTCCTCGAAAGAATCAGCACCTGTGTTTACGTCGAAAGAGTTGGAAGTTGCAAGAAAGGAAAGATTGGATGGACTGGGACCGTTCGTGTCTCGGCTGCCTAAGAAATGGATACCGTATGCGGAGCTGATGAGGCTAGAGAAACCCGTGGGCACGTGGCTGTTATATTTGCCCTGCAGTTGGTCTATACTTATGGGAGCCATGATGCAAGGTGCTACATTGAGCGCAACAGCTGGTATGTTGGGTATTTTCGGTGTAGGTGCATTGGTAATGAGAGGTGCTGGCTGCACCATCAACGATTTTTTGGATAGAAAGTTGGATCAAAGAGTTATCAGGTCCGTCGAGAGGCCTATCGCCTCTGGTAGAGTGAGCCCCCGTCGGGCGTTAGTATTCTTGGGGGCTCAAACTCTTGTTGGAATGGGCGTTCTATCTTTGCTTCCTGCGCAGTGTTGGTGGCTAGGCCTTGCATCGTTACCTATTGTGTTCACATACCCTTTGTTTAAGCGGTTTACGTACTATCCTCAAGCTGCATTAAGTGCATGTTTCAATTGGGGAGCGTTACTTGGGTTTCCTGCCATGGGTGTAATGAGCTGGCCTACAATGATACCTTTGTACCTGAGCAGTTACTTGTGGTGTATGACTTACGATACTATATACGCACACCAGGATAAAAAGTTTGACATCAAGACTGGAATCAAGTCTACCGCTTTGGCTTGGGGTCCACGCACAAAGTCTATCATGAAGGCCATGTCCGCGTCTCAAATCGCACTGTTAGCTGTCGCCGGCTTGAACAGTGGGTTGTTATGGGGGCCTGGGTTCATTGGTGGACTAGGAGTCTTCGCTTATAGACTCTTCAGCATGATAAAGAAAGTGGATCTTGACAATCCTAAAAACTGCTGGAAGTATTTTAATGCAAATATCAACACCGGACTTTACTTTACGTACGCCTTGGCAGTCGACTACATCTTGAGACTGTTTGGATTCTTGTAG","protein_sequence":"MFIWQRKSILLGRSILGSGRVTVAGIIGSSRKRYTSSSSSSSSPSSKESAPVFTSKELEVARKERLDGLGPFVSRLPKKWIPYAELMRLEKPVGTWLLYLPCSWSILMGAMMQGATLSATAGMLGIFGVGALVMRGAGCTINDFLDRKLDQRVIRSVERPIASGRVSPRRALVFLGAQTLVGMGVLSLLPAQCWWLGLASLPIVFTYPLFKRFTYYPQAALSACFNWGALLGFPAMGVMSWPTMIPLYLSSYLWCMTYDTIYAHQDKKFDIKAGIKSTALAWGPRTKSIMKAMSASQIALLAVAGLNSGLLWGPGFIGGLGVFAYRLFSMIKKVDLDNPKNCWKYFNANINTGLYFTYALAVDYILRLFGFL"},{"created_at":"2011-05-27T05:07:16.000Z","updated_at":"2011-05-27T15:01:23.000Z","name":"Protein farnesyltransferase subunit beta","uniprot_id":"P22007","uniprot_name":"FNTB_YEAST","enzyme":true,"transporter":false,"gene_name":"RAM1","num_residues":431,"molecular_weight":"48189.39844","theoretical_pi":"6.35","general_function":"Involved in catalytic activity","specific_function":"Catalyzes the transfer of a farnesyl moiety from farnesyl pyrophosphate to a cysteine at the fourth position from the C-terminus of several proteins such as a-factor and RAS. The beta subunit is responsible for peptide-binding","reactions":[{"id":2761,"direction":"\u003e","locations":"","altext":"Farnesyl diphosphate + protein-cysteine = S-farnesyl protein + diphosphate.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"M22753","genbank_protein_id":"171420","gene_card_id":"RAM1","chromosome_location":"chromosome 4","locus":"YDL090C","synonyms":["FTase-beta","CAAX farnesyltransferase subunit beta","Ras proteins prenyltransferase subunit beta"],"enzyme_classes":["2.5.1.58"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Prenyltrans","identifier":"PF00432"}],"pathways":[],"gene_sequence":"ATGCGACAGAGAGTAGGAAGGTCCATAGCTAGGGCTAAATTTATAAATACTGCCTTATTAGGAAGAAAGAGACCAGTTATGGAAAGAGTCGTCGATATAGCGCATGTAGATTCAAGTAAAGCAATCCAACCATTGATGAAGGAACTAGAAACCGACACTACAGAAGCACGATACAAAGTACTACAAAGTGTATTAGAGATATACGATGATGAAAAGAATATAGAACCTGCTCTCACGAAAGAGTTTCACAAAATGTACTTGGATGTCGCTTTTGAGATATCGTTACCTCCACAAATGACAGCACTAGATGCTTCACAACCGTGGATGCTATATTGGATTGCTAACTCATTGAAGGTAATGGACAGAGACTGGCTTTCAGATGACACCAAAAGAAAAATTGTAGATAAGCTCTTTACTATTAGTCCTTCAGGAGGACCCTTTGGTGGAGGTCCTGGCCAATTATCTCATTTGGCCAGCACTTATGCTGCAATTAATGCTCTCTCCCTTTGCGATAACATAGATGGATGCTGGGACAGAATTGATCGAAAAGGAATTTACCAATGGCTGATATCGTTGAAAGAGCCTAATGGAGGATTCAAGACCTGTTTAGAAGTCGGAGAAGTGGATACAAGAGGTATATACTGTGCCTTGAGCATAGCAACCTTATTAAATATTCTTACAGAAGAGCTTACAGAAGGTGTGTTAAACTATTTGAAAAATTGTCAAAATTATGAAGGTGGATTCGGCAGTTGTCCTCACGTAGATGAGGCACACGGAGGCTATACTTTCTGTGCTACAGCTAGTCTAGCAATTTTAAGGTCCATGGACCAAATAAATGTTGAAAAGCTTTTAGAATGGTCTAGTGCTCGTCAATTGCAAGAAGAACGAGGATTTTGCGGAAGGAGCAACAAACTTGTTGACGGTTGCTATAGTTTTTGGGTTGGAGGTTCGGCTGCCATTCTTGAAGCTTTTGGATATGGCCAATGCTTCAACAAACATGCTCTTCGGGACTACATATTGTACTGTTGCCAAGAAAAAGAGCAACCTGGTTTGAGAGATAAACCAGGGGCCCACTCAGACTTTTACCATACAAATTATTGCCTATTAGGACTGGCTGTTGCGGAAAGTTCATACAGTTGCACTCCTAATGATTCTCCACATAATATTAAGTGTACTCCAGACCGCCTAATTGGATCATCGAAACTTACTGATGTCAACCCTGTCTATGGTTTACCAATAGAAAATGTAAGAAAAATTATCCACTACTTTAAATCCAATTTATCTTCTCCAAGTTAA","protein_sequence":"MRQRVGRSIARAKFINTALLGRKRPVMERVVDIAHVDSSKAIQPLMKELETDTTEARYKVLQSVLEIYDDEKNIEPALTKEFHKMYLDVAFEISLPPQMTALDASQPWMLYWIANSLKVMDRDWLSDDTKRKIVDKLFTISPSGGPFGGGPGQLSHLASTYAAINALSLCDNIDGCWDRIDRKGIYQWLISLKEPNGGFKTCLEVGEVDTRGIYCALSIATLLNILTEELTEGVLNYLKNCQNYEGGFGSCPHVDEAHGGYTFCATASLAILRSMDQINVEKLLEWSSARQLQEERGFCGRSNKLVDGCYSFWVGGSAAILEAFGYGQCFNKHALRDYILYCCQEKEQPGLRDKPGAHSDFYHTNYCLLGLAVAESSYSCTPNDSPHNIKCTPDRLIGSSKLTDVNPVYGLPIENVRKIIHYFKSNLSSPS"}]}