{"ymdb_id":"YMDB00460","created_at":"2011-05-29T18:19:11.000Z","updated_at":"2016-09-08T18:35:30.000Z","name":"3-Hexaprenyl-4,5-dihydroxybenzoic acid","cas":"63975-40-6","state":"Solid","melting_point":"","description":"3-Hexaprenyl-4,5-dihydroxybenzoic acid is an intermediate in the ubiquinol-6 biosynthesis (eukaryotic) pathway. It is a substrate for hexaprenyldihydroxybenzoate methyltransferase. Ubiquinone (coenzyme Q) is an isoprenoid quinone that functions as an electron carrier in membranes. [Biocyc PWY3O-19]","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"mitochondrion;cytoplasm","synthesis_reference":null,"chebi_id":"18081","hmdb_id":"HMDB01063","kegg_id":"C05200","pubchem_id":"194172","cs_id":null,"foodb_id":null,"wikipedia_link":null,"biocyc_id":"3-HEXAPRENYL-45-DIHYDROXYBENZOATE","iupac":"3-[(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-yl]-4,5-dihydroxybenzoic acid","traditional_iupac":"dhhpba","logp":"11.050836455000002","pka":"9.279265526650002","alogps_solubility":"5.73e-04 g/l","alogps_logp":"8.41","alogps_logs":"-5.99","acceptor_count":"4","donor_count":"3","rotatable_bond_count":"18","polar_surface_area":"77.75999999999999","refractivity":"180.53180000000003","polarizability":"70.24551759046041","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"-6.349574389344849","pka_strongest_acidic":"4.1281674458459845","bioavailability":"0","number_of_rings":"1","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["3-Hexaprenyl-4,5-Dihydroxybenzoate","3-Hexaprenyl-4,5-Dihydroxybenzoic acid","3,4-Dihydroxy-5-hexaprenylbenzoate","3,4-Dihydroxy-5-hexaprenylbenzoic acid","Dhhpba"],"pathways":[{"name":"Ubiquinone and other terpenoid-quinone biosynthesis","kegg_map_id":"00130"},{"name":"Ubiquinone Biosynthesis","kegg_map_id":null}],"growth_conditions":[],"references":[{"pubmed_id":21051339,"citation":"UniProt Consortium (2011). \"Ongoing and future developments at the Universal Protein Resource.\" Nucleic Acids Res 39:D214-D219."},{"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":15792955,"citation":"Marbois, B., Gin, P., Faull, K. F., Poon, W. W., Lee, P. T., Strahan, J., Shepherd, J. N., Clarke, C. F. (2005). \"Coq3 and Coq4 define a polypeptide complex in yeast mitochondria for the biosynthesis of coenzyme Q.\" J Biol Chem 280:20231-20238."}],"proteins":[{"created_at":"2011-05-26T16:35:40.000Z","updated_at":"2011-05-29T05:06:18.000Z","name":"Hexaprenyldihydroxybenzoate methyltransferase, mitochondrial","uniprot_id":"P27680","uniprot_name":"COQ3_YEAST","enzyme":true,"transporter":false,"gene_name":"COQ3","num_residues":312,"molecular_weight":"36330.60156","theoretical_pi":"6.98","general_function":"Involved in methyltransferase activity","specific_function":"Non-specific O-methyltransferase that catalyzes the 2 O- methylation steps in the ubiquinone biosynthetic pathway","reactions":[{"id":2429,"direction":"\u003e","locations":"Mitochondrion inner membrane; Peripheral membrane protein; Matrix side","altext":"S-adenosyl-L-methionine + 3,4-dihydroxy-5-all-trans-polyprenylbenzoate = S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-5-all-trans-polyprenylbenzoate.","export":false,"pw_reaction_id":null,"source":null},{"id":2430,"direction":"\u003e","locations":"Mitochondrion inner membrane; Peripheral membrane protein; Matrix side","altext":"S-adenosyl-L-methionine + 3-demethylubiquinone-n = S-adenosyl-L-homocysteine + ubiquinone-n.","export":false,"pw_reaction_id":null,"source":null},{"id":2431,"direction":"\u003e","locations":"Mitochondrion inner membrane; Peripheral membrane protein; Matrix side","altext":"S-adenosyl-L-methionine + 2-hexaprenyl-3-methyl-5-hydroxy-6-methoxy-1,4-benzoquinol = S-adenosyl-L-homocysteine + ubiquinol.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Mitochondrion inner membrane; Peripheral membrane protein; Matrix side","genbank_gene_id":"M73270","genbank_protein_id":"171392","gene_card_id":"COQ3","chromosome_location":"chromosome 15","locus":"YOL096C","synonyms":["3,4-dihydroxy-5-hexaprenylbenzoate methyltransferase","DHHB methyltransferase","DHHB-MT","DHHB-MTase","Dihydroxyhexaprenylbenzoate methyltransferase"],"enzyme_classes":["2.1.1.114","2.1.1.64"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" quinone cofactor methyltransferase activity"},{"category":"Function","description":" 2-polyprenyl-6-methoxy-1,4-benzoquinone methyltransferase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring one-carbon groups"},{"category":"Function","description":" methyltransferase activity"},{"category":"Function","description":" C-methyltransferase activity"},{"category":"Process","description":" oxidoreduction coenzyme metabolic process"},{"category":"Process","description":" ubiquinone metabolic process"},{"category":"Process","description":" ubiquinone biosynthetic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cofactor metabolic process"},{"category":"Process","description":" coenzyme metabolic process"}],"pfams":[{"name":"Methyltransf_11","identifier":"PF08241"}],"pathways":[{"name":"Ubiquinone and other terpenoid-quinone biosynthesis","kegg_map_id":"00130"}],"gene_sequence":"ATGGGATTCATAATGTTGTTAAGATCTAGATTTTTGAAGGTTATTCATGTGAGGAAACAATTGAGCGCCTGTTCAAGATTTGCAATTCAAACACAAACGAGATGTAAGAGCACAGATGCTTCTGAAGATGAAGTGAAGCATTTCCAGGAGCTAGCCCCTACTTGGTGGGATACAGACGGATCACAAAGAATTCTACACAAAATGAATCTAACTAGGTTAGATTTTGTGCAGAGGACTGTGAGGAACCAGGTTAAAATTCAGAATCCTGAAATATTTGTCCCTGGATTTAATTACAAGGAGTTTCTACCAGAATACGTCTGCGACAATATTCAGCGGGAAATGCAGGAAAGCATAGAGACTAATCTAGATAAGAGGCCAGAAGTGAGCGTCTTGGATGTTGGATGCGGTGGTGGCATTTTGAGTGAATCGCTCGCGAGACTAAAATGGGTGAAGAATGTTCAAGGGATCGATCTGACTCGCGATTGTATCATGGTAGCAAAAGAGCATGCCAAGAAAGACCCCATGCTGGAGGGAAAGATAAATTATGAGTGCAAGGCTCTGGAGGATGTTACTGGACAATTTGATATTATCACCTGTATGGAAATGCTAGAGCACGTGGATATGCCTAGTGAAATTTTAAGGCATTGTTGGTCGAGGTTAAATCCCGAAAAAGGTATACTCTTTTTAAGTACTATAAACAGAGATCTCATCTCATGGTTTACTACAATTTTTATGGGTGAAAACGTCTTGAAGATCGTCCCAAAGGGTACTCATCATTTGAGCAAATACATAAACTCAAAGGAAATCCTTGCCTGGTTCAATGACAACTACAGTGGCCAATTTCGCTTGTTGGATCTCAAGGGGACCATGTACCTCCCATATCAAGGGTGGGTTGAGCACGATTGTTCCGATGTCGGTAATTATTTTATGGCTATTCAGAGACTGAATTGA","protein_sequence":"MLLRSRFLKVIHVRKQLSACSRFAIQTQTRCKSTDASEDEVKHFQELAPTWWDTDGSQRILHKMNLTRLDFVQRTVRNQVKIQNPEIFVPGFNYKEFLPEYVCDNIQREMQESIETNLDKRPEVSVLDVGCGGGILSESLARLKWVKNVQGIDLTRDCIMVAKEHAKKDPMLEGKINYECKALEDVTGQFDIITCMEMLEHVDMPSEILRHCWSRLNPEKGILFLSTINRDLISWFTTIFMGENVLKIVPKGTHHLSKYINSKEILAWFNDNYSGQFRLLDLKGTMYLPYQGWVEHDCSDVGNYFMAIQRLN"},{"created_at":"2011-05-27T02:37:10.000Z","updated_at":"2011-05-29T05:06:36.000Z","name":"Ubiquinone biosynthesis protein COQ4, mitochondrial","uniprot_id":"O13525","uniprot_name":"COQ4_YEAST","enzyme":true,"transporter":false,"gene_name":"COQ4","num_residues":335,"molecular_weight":"38626.80078","theoretical_pi":"10.13","general_function":"Involved in ubiquinone biosynthetic process","specific_function":"Component of the coenzyme Q biosynthetic pathway. May play a role in organizing a multi-subunit COQ enzyme complex required for coenzyme Q biosynthesis. Required for steady-state levels of COQ3, COQ4, COQ6, COQ7 and COQ9 polypeptides","reactions":[],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Mitochondrion inner membrane; Peripheral membrane protein; Matrix side","genbank_gene_id":"Z68194","genbank_protein_id":"1204149","gene_card_id":"COQ4","chromosome_location":"chromosome 4","locus":"YDR204W","synonyms":["Coenzyme Q biosynthesis protein 4"],"enzyme_classes":[],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" Not Available"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cofactor metabolic process"},{"category":"Process","description":" coenzyme metabolic process"},{"category":"Process","description":" oxidoreduction coenzyme metabolic process"},{"category":"Process","description":" ubiquinone metabolic process"},{"category":"Process","description":" ubiquinone biosynthetic process"}],"pfams":[{"name":"Coq4","identifier":"PF05019"}],"pathways":[],"gene_sequence":"ATGTTGAGGTTATCTTTACTGAGATCAACAGCTACTTTGCCAGTGAAATGCCAACGTCGTGGGCTAATATTACCTGCGGCGGCAATGTACACCTTAGGCTCATTAATATTTGGTAAGGAAGCAAGGTTGGCGGATGCCATGGAACGTGGTGAGTTACATAACAAGAACGTTGATTATGCGAAAGAAGCTGAAGAGCGTACCGAGTTACGTATTAGGGCCCTGGCTAATACTCGGCCAATGGAACCTCGGTACAACGGCCATGTTCCCCTTCATCGGTACGAGAAATTGCTGCTGTTTGCAATTTCCGGTTGGAATTCATTTTTCCATCCTGAAGATGGTTATAATATTGTACAATTGGGTGAGGCAACTGCATTGCCGGTCTTCTTGGAGAATTTGAAGCAAACAATGTTAAGTGATTCCTCTGGGAGGCGCATTTTGAAGGAACAACCCAATATCACAACAGAGATTTTGCATATGGACAAACTAGCTAAATTGCCACATAACACGTTTGGGTATGTATATTACCAATGGTTGAAAAGAGAAAACGTTTCTCCGGACACTAGAGCACCTGTCAAATTTATCGACGATCCTATGCATGCATATATCTTTAAGAGGTATAGACAATGCCACGATTTCTATCACGCTATAACCAACATGCCTATTATCATTGAGGGGGAGATCACCATAAAGGCTCTTGAAGGTGCCAACCTGGGCGTCCCAATGGCCATTCTCGGTGGTATCCTTGCACCTTTACGTTTGAAAAAGGTGCAAAGAAAAAGATTATATAATATATATCTCCCTTGGGCTGTCAGAACAGGTTTAAGCTGCAAGCCATTGATCAACGTGTATTGGGAGGAAATGCTGGAGAAGGATGTTACTGCTTTGAGGAAAGAGCTAAAGATAACACTCCCTCCGGATCTAAGGACAATGAGGAAGGAGCGTGCAGCCCTTAGGAAGGAGATTGACGCAAAATACAACTCACAGAAACGAGCCACGACTCCAGCATGA","protein_sequence":"MLRLSLLRSTATLPVKCQRRGLILPAAAMYTLGSLIFGKEARLADAMERGELHNKNVDYAKEAEERTELRIRALANTRPMEPRYNGHVPLHRYEKLLLFAISGWNSFFHPEDGYNIVQLGEATALPVFLENLKQTMLSDSSGRRILKEQPNITTEILHMDKLAKLPHNTFGYVYYQWLKRENVSPDTRAPVKFIDDPMHAYIFKRYRQCHDFYHAITNMPIIIEGEITIKALEGANLGVPMAILGGILAPLRLKKVQRKRLYNIYLPWAVRTGLSCKPLINVYWEEMLEKDVTALRKELKITLPPDLRTMRKERAALRKEIDAKYNSQKRATTPA"}]}