{"ymdb_id":"YMDB00100","created_at":"2011-05-29T15:56:45.000Z","updated_at":"2016-09-08T18:35:01.000Z","name":"3-Dehydroquinate","cas":"105735-75-9","state":"Solid","melting_point":null,"description":"3-Dehydroquinic acid (DHQ) is the first carbocyclic intermediate of the shikimate pathway. It is created from 3-deoxyarabinoheptulosonate 7-phosphate, a 7-carbon ulonic acid, by the enzyme DHQ synthase. The mechanism of ring closure is complex, but involves an aldol condensation at C-2 and C-7. It has the same structure as quinic acid, which is found in coffee, but the C-3 hydroxyl is oxidized to a ketone group. 3-Dehydroquinic acid undergoes five further enzymatic steps in the remainder of the shikimate pathway to chorismic acid, a precursor to tyrosine, 3-phenylalanine, tryptophan, Vitamin K and folate. 3-Dehydroquinate can also be a precursor to pyrroloquinoline quinone(PQQ), an alternate redox coenzyme involved in oxidative phosphorylation. [Wikipedia]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":"Cytoplasm","synthesis_reference":null,"chebi_id":"17947","hmdb_id":"HMDB12710","kegg_id":"C00944","pubchem_id":"630","cs_id":"23095481","foodb_id":null,"wikipedia_link":"3-Dehydroquinic_acid","biocyc_id":"CPD-10229","iupac":"(1R,3R,4S)-1,3,4-trihydroxy-5-oxocyclohexane-1-carboxylic acid","traditional_iupac":"3-dehydroquinic acid","logp":"-2.0552498786666664","pka":"12.359570129279923","alogps_solubility":"7.02e+02 g/l","alogps_logp":"-2.05","alogps_logs":"0.57","acceptor_count":"6","donor_count":"4","rotatable_bond_count":"1","polar_surface_area":"115.06000000000002","refractivity":"38.6974","polarizability":"16.45823621642952","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"-3.272742784069651","pka_strongest_acidic":"3.304489138555496","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["3-Dehydroquinic acid","5-Dehydroquinate","5-dehydroquinic acid","Cyclohexan-1,4,5-triol-3-one-1-carboxylic acid"],"pathways":[{"name":"Phenylalanine, tyrosine and tryptophan biosynthesis","kegg_map_id":"00400"}],"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."}],"proteins":[{"created_at":"2011-05-24T20:47:22.000Z","updated_at":"2011-07-22T17:53:48.000Z","name":"Pentafunctional AROM polypeptide","uniprot_id":"P08566","uniprot_name":"ARO1_YEAST","enzyme":true,"transporter":false,"gene_name":"ARO1","num_residues":1588,"molecular_weight":"174754.0","theoretical_pi":"6.22","general_function":"Involved in 3-dehydroquinate dehydratase activity","specific_function":"The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis","reactions":[{"id":1162,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1163,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1187,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1965,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1966,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2343,"direction":"\u003e","locations":"Cytoplasm","altext":"3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate = 3-dehydroquinate + phosphate.","export":false,"pw_reaction_id":null,"source":null},{"id":2344,"direction":"\u003e","locations":"Cytoplasm","altext":"3-dehydroquinate = 3-dehydroshikimate + H(2)O.","export":false,"pw_reaction_id":null,"source":null},{"id":2345,"direction":"\u003e","locations":"Cytoplasm","altext":"Shikimate + NADP(+) = 3-dehydroshikimate + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":2346,"direction":"\u003e","locations":"Cytoplasm","altext":"ATP + shikimate = ADP + shikimate 3-phosphate.","export":false,"pw_reaction_id":null,"source":null},{"id":2347,"direction":"\u003e","locations":"Cytoplasm","altext":"Phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasm","genbank_gene_id":"X06077","genbank_protein_id":"3381","gene_card_id":"ARO1","chromosome_location":"chromosome 4","locus":"YDR127W","synonyms":["3-dehydroquinate synthase","3-phosphoshikimate 1-carboxyvinyltransferase","5-enolpyruvylshikimate-3-phosphate synthase","EPSP synthase","EPSPS","Shikimate kinase","3-dehydroquinate dehydratase","3-dehydroquinase","Shikimate dehydrogenase"],"enzyme_classes":["4.2.3.4","2.5.1.19","2.7.1.71","4.2.1.10","1.1.1.25"],"go_classes":[{"category":"Component","description":" intracellular part"},{"category":"Component","description":" cytoplasm"},{"category":"Component","description":" cell part"},{"category":"Function","description":" carbon-oxygen lyase activity"},{"category":"Function","description":" hydro-lyase activity"},{"category":"Function","description":" shikimate kinase activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" shikimate 5-dehydrogenase activity"},{"category":"Function","description":" transferase activity, transferring alkyl or aryl (other than methyl) groups"},{"category":"Function","description":" 3-phosphoshikimate 1-carboxyvinyltransferase activity"},{"category":"Function","description":" nucleoside binding"},{"category":"Function","description":" carbon-oxygen lyase activity, acting on phosphates"},{"category":"Function","description":" purine nucleoside binding"},{"category":"Function","description":" 3-dehydroquinate synthase activity"},{"category":"Function","description":" adenyl nucleotide binding"},{"category":"Function","description":" 3-dehydroquinate dehydratase activity"},{"category":"Function","description":" adenyl ribonucleotide binding"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" ATP binding"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Function","description":" kinase activity"},{"category":"Function","description":" transferase activity, transferring phosphorus-containing groups"},{"category":"Function","description":" oxidoreductase activity, acting on CH-OH group of donors"},{"category":"Function","description":" lyase activity"},{"category":"Function","description":" oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor"},{"category":"Process","description":" cellular amino acid biosynthetic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" cellular amino acid and derivative metabolic process"},{"category":"Process","description":" cellular amino acid metabolic process"},{"category":"Process","description":" aromatic amino acid family biosynthetic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" oxidation reduction"}],"pfams":[{"name":"DHQ_synthase","identifier":"PF01761"},{"name":"DHquinase_I","identifier":"PF01487"},{"name":"EPSP_synthase","identifier":"PF00275"},{"name":"Shikimate_DH","identifier":"PF01488"},{"name":"Shikimate_dh_N","identifier":"PF08501"},{"name":"SKI","identifier":"PF01202"}],"pathways":[{"name":"Phenylalanine, tyrosine and tryptophan biosynthesis","kegg_map_id":"00400"}],"gene_sequence":"ATGGTGCAGTTAGCCAAAGTCCCAATTCTAGGAAATGATATTATCCACGTTGGGTATAACATTCATGACCATTTGGTTGAAACCATAATTAAACATTGTCCTTCTTCGACATACGTTATTTGCAATGATACGAACTTGAGTAAAGTTCCATACTACCAGCAATTAGTCCTGGAATTCAAGGCTTCTTTGCCAGAAGGCTCTCGTTTACTTACTTATGTTGTTAAACCAGGTGAGACAAGTAAAAGTAGAGAAACCAAAGCGCAGCTAGAAGATTATCTTTTAGTGGAAGGATGTACTCGTGATACGGTTATGGTAGCGATCGGTGGTGGTGTTATTGGTGACATGATTGGGTTCGTTGCATCTACATTTATGAGAGGTGTTCGTGTTGTCCAAGTACCAACATCCTTATTGGCAATGGTCGATTCCTCCATTGGTGGTAAAACTGCTATTGACACTCCTCTAGGTAAAAACTTTATTGGTGCATTTTGGCAACCAAAATTTGTCCTTGTAGATATTAAATGGCTAGAAACGTTAGCCAAGAGAGAGTTTATCAATGGGATGGCAGAAGTTATCAAGACTGCTTGTATTTGGAACGCTGACGAATTTACTAGATTAGAATCAAACGCTTCGTTGTTCTTAAATGTTGTTAATGGGGCAAAAAATGTCAAGGTTACCAATCAATTGACAAACGAGATTGACGAGATATCGAATACAGATATTGAAGCTATGTTGGATCATACATATAAGTTAGTTCTTGAGAGTATTAAGGTCAAAGCGGAAGTTGTCTCTTCGGATGAACGTGAATCCAGTCTAAGAAACCTTTTGAACTTCGGACATTCTATTGGTCATGCTTATGAAGCTATACTAACCCCACAAGCATTACATGGTGAATGTGTGTCCATTGGTATGGTTAAAGAGGCGGAATTATCCCGTTATTTCGGTATTCTCTCCCCTACCCAAGTTGCACGTCTATCCAAGATTTTGGTTGCCTACGGGTTGCCTGTTTCGCCTGATGAGAAATGGTTTAAAGAGCTAACCTTACATAAGAAAACACCATTGGATATCTTATTGAAGAAAATGAGTATTGACAAGAAAAACGAGGGTTCCAAAAAGAAGGTGGTCATTTTAGAAAGTATTGGTAAGTGCTATGGTGACTCCGCTCAATTTGTTAGCGATGAAGACCTGAGATTTATTCTAACAGATGAAACCCTCGTTTACCCCTTCAAGGACATCCCTGCTGATCAACAGAAAGTTGTTATCCCCCCTGGTTCTAAGTCCATCTCCAATCGTGCTTTAATTCTTGCTGCCCTCGGTGAAGGTCAATGTAAAATCAAGAACTTATTACATTCTGATGATACTAAACATATGTTAACCGCTGTTCATGAATTGAAAGGTGCTACGATATCATGGGAAGATAATGGTGAGACGGTAGTGGTGGAAGGACATGGTGGTTCCACATTGTCAGCTTGTGCTGACCCCTTATATCTAGGTAATGCAGGTACTGCATCTAGATTTTTGACTTCCTTGGCTGCCTTGGTCAATTCTACTTCAAGCCAAAAGTATATCGTTTTAACTGGTAACGCAAGAATGCAACAAAGACCAATTGCTCCTTTGGTCGATTCTTTGCGTGCTAATGGTACTAAAATTGAGTACTTGAATAATGAAGGTTCCCTGCCAATCAAAGTTTATACTGATTCGGTATTCAAAGGTGGTAGAATTGAATTAGCTGCTACAGTTTCTTCTCAGTACGTATCCTCTATCTTGATGTGTGCCCCATACGCTGAAGAACCTGTAACTTTGGCTCTTGTTGGTGGTAAGCCAATCTCTAAATTGTACGTCGATATGACAATAAAAATGATGGAAAAATTCGGTATCAATGTTGAAACTTCTACTACAGAACCTTACACTTATTATATTCCAAAGGGACATTATATTAACCCATCAGAATACGTCATTGAAAGTGATGCCTCAAGTGCTACATACCCATTGGCCTTCGCCGCAATGACTGGTACTACCGTAACGGTTCCAAACATTGGTTTTGAGTCGTTACAAGGTGATGCCAGATTTGCAAGAGATGTCTTGAAACCTATGGGTTGTAAAATAACTCAAACGGCAACTTCAACTACTGTTTCGGGTCCTCCTGTAGGTACTTTAAAGCCATTAAAACATGTTGATATGGAGCCAATGACTGATGCGTTCTTAACTGCATGTGTTGTTGCCGCTATTTCGCACGACAGTGATCCAAATTCTGCAAATACAACCACCATTGAAGGTATTGCAAACCAGCGTGTCAAAGAGTGTAACAGAATTTTGGCCATGGCTACAGAGCTCGCCAAATTTGGCGTCAAAACTACAGAATTACCAGATGGTATTCAAGTCCATGGTTTAAACTCGATAAAAGATTTGAAGGTTCCTTCCGACTCTTCTGGACCTGTCGGTGTATGCACATATGATGATCATCGTGTGGCCATGAGTTTCTCGCTTCTTGCAGGAATGGTAAATTCTCAAAATGAACGTGACGAAGTTGCTAATCCTGTAAGAATACTTGAAAGACATTGTACTGGTAAAACCTGGCCTGGCTGGTGGGATGTGTTACATTCCGAACTAGGTGCCAAATTAGATGGTGCAGAACCTTTAGAGTGCACATCCAAAAAGAACTCAAAGAAAAGCGTTGTCATTATTGGCATGAGAGCAGCTGGCAAAACTACTATAAGTAAATGGTGCGCATCCGCTCTGGGTTACAAATTAGTTGACCTAGACGAGCTGTTTGAGCAACAGCATAACAATCAAAGTGTTAAACAATTTGTTGTGGAGAACGGTTGGGAGAAGTTCCGTGAGGAAGAAACAAGAATTTTCAAGGAAGTTATTCAAAATTACGGCGATGATGGATATGTTTTCTCAACAGGTGGCGGTATTGTTGAAAGCGCTGAGTCTAGAAAAGCCTTAAAAGATTTTGCCTCATCAGGTGGATACGTTTTACACTTACATAGGGATATTGAGGAGACAATTGTCTTTTTACAAAGTGATCCTTCAAGACCTGCCTATGTGGAAGAAATTCGTGAAGTTTGGAACAGAAGGGAGGGGTGGTATAAAGAATGCTCAAATTTCTCTTTCTTTGCTCCTCATTGCTCCGCAGAAGCTGAGTTCCAAGCTCTAAGAAGATCGTTTAGTAAGTACATTGCAACCATTACAGGTGTCAGAGAAATAGAAATTCCAAGCGGAAGATCTGCCTTTGTGTGTTTAACCTTTGATGACTTAACTGAACAAACTGAGAATTTGACTCCAATCTGTTATGGTTGTGAGGCTGTAGAGGTCAGAGTAGACCATTTGGCTAATTACTCTGCTGATTTCGTGAGTAAACAGTTATCTATATTGCGTAAAGCCACTGACAGTATTCCTATCATTTTTACTGTGCGAACCATGAAGCAAGGTGGCAACTTTCCTGATGAAGAGTTCAAAACCTTGAGAGAGCTATACGATATTGCCTTGAAGAATGGTGTTGAATTCCTTGACTTAGAACTAACTTTACCTACTGATATCCAATATGAGGTTATTAACAAAAGGGGCAACACCAAGATCATTGGTTCCCATCATGACTTCCAAGGATTATACTCCTGGGACGACGCTGAATGGGAAAACAGATTCAATCAAGCGTTAACTCTTGATGTGGATGTTGTAAAATTTGTGGGTACGGCTGTTAATTTCGAAGATAATTTGAGACTGGAACACTTTAGGGATACACACAAGAATAAGCCTTTAATTGCAGTTAATATGACTTCTAAAGGTAGCATTTCTCGTGTTTTGAATAATGTTTTAACACCTGTGACATCAGATTTATTGCCTAACTCCGCTGCCCCTGGCCAATTGACAGTAGCACAAATTAACAAGATGTATACATCTATGGGAGGTATCGAGCCTAAGGAACTGTTTGTTGTTGGAAAGCCAATTGGCCACTCTAGATCGCCAATTTTACATAACACTGGCTATGAAATTTTAGGTTTACCTCACAAGTTCGATAAATTTGAAACTGAATCCGCACAATTGGTGAAAGAAAAACTTTTGGACGGAAACAAGAACTTTGGCGGTGCTGCAGTCACAATTCCTCTGAAATTAGATATAATGCAGTACATGGATGAATTGACTGATGCTGCTAAAGTTATTGGTGCTGTAAACACAGTTATACCATTGGGTAACAAGAAGTTTAAGGGTGATAATACCGACTGGTTAGGTATCCGTAATGCCTTAATTAACAATGGCGTTCCCGAATATGTTGGTCATACCGCTGGTTTGGTTATCGGTGCAGGTGGCACTTCTAGAGCCGCCCTTTACGCCTTGCACAGTTTAGGTTGCAAAAAGATCTTCATAATCAACAGGACAACTTCGAAATTGAAGCCATTAATAGAGTCACTTCCATCTGAATTCAACATTATTGGAATAGAGTCCACTAAATCTATAGAAGAGATTAAGGAACACGTTGGCGTTGCTGTCAGCTGTGTACCAGCCGACAAACCATTAGATGACGAACTTTTAAGTAAGCTGGAGAGATTCCTTGTGAAAGGTGCCCATGCTGCTTTTGTACCAACCTTATTGGAAGCCGCATACAAACCAAGCGTTACTCCCGTTATGACAATTTCACAAGACAAATATCAATGGCACGTTGTCCCTGGATCACAAATGTTAGTACACCAAGGTGTAGCTCAGTTTGAAAAGTGGACAGGATTCAAGGGCCCTTTCAAGGCCATTTTTGATGCCGTTACGAAAGAGTAG","protein_sequence":"MVQLAKVPILGNDIIHVGYNIHDHLVETIIKHCPSSTYVICNDTNLSKVPYYQQLVLEFKASLPEGSRLLTYVVKPGETSKSRETKAQLEDYLLVEGCTRDTVMVAIGGGVIGDMIGFVASTFMRGVRVVQVPTSLLAMVDSSIGGKTAIDTPLGKNFIGAFWQPKFVLVDIKWLETLAKREFINGMAEVIKTACIWNADEFTRLESNASLFLNVVNGAKNVKVTNQLTNEIDEISNTDIEAMLDHTYKLVLESIKVKAEVVSSDERESSLRNLLNFGHSIGHAYEAILTPQALHGECVSIGMVKEAELSRYFGILSPTQVARLSKILVAYGLPVSPDEKWFKELTLHKKTPLDILLKKMSIDKKNEGSKKKVVILESIGKCYGDSAQFVSDEDLRFILTDETLVYPFKDIPADQQKVVIPPGSKSISNRALILAALGEGQCKIKNLLHSDDTKHMLTAVHELKGATISWEDNGETVVVEGHGGSTLSACADPLYLGNAGTASRFLTSLAALVNSTSSQKYIVLTGNARMQQRPIAPLVDSLRANGTKIEYLNNEGSLPIKVYTDSVFKGGRIELAATVSSQYVSSILMCAPYAEEPVTLALVGGKPISKLYVDMTIKMMEKFGINVETSTTEPYTYYIPKGHYINPSEYVIESDASSATYPLAFAAMTGTTVTVPNIGFESLQGDARFARDVLKPMGCKITQTATSTTVSGPPVGTLKPLKHVDMEPMTDAFLTACVVAAISHDSDPNSANTTTIEGIANQRVKECNRILAMATELAKFGVKTTELPDGIQVHGLNSIKDLKVPSDSSGPVGVCTYDDHRVAMSFSLLAGMVNSQNERDEVANPVRILERHCTGKTWPGWWDVLHSELGAKLDGAEPLECTSKKNSKKSVVIIGMRAAGKTTISKWCASALGYKLVDLDELFEQQHNNQSVKQFVVENGWEKFREEETRIFKEVIQNYGDDGYVFSTGGGIVESAESRKALKDFASSGGYVLHLHRDIEETIVFLQSDPSRPAYVEEIREVWNRREGWYKECSNFSFFAPHCSAEAEFQALRRSFSKYIATITGVREIEIPSGRSAFVCLTFDDLTEQTENLTPICYGCEAVEVRVDHLANYSADFVSKQLSILRKATDSIPIIFTVRTMKQGGNFPDEEFKTLRELYDIALKNGVEFLDLELTLPTDIQYEVINKRGNTKIIGSHHDFQGLYSWDDAEWENRFNQALTLDVDVVKFVGTAVNFEDNLRLEHFRDTHKNKPLIAVNMTSKGSISRVLNNVLTPVTSDLLPNSAAPGQLTVAQINKMYTSMGGIEPKELFVVGKPIGHSRSPILHNTGYEILGLPHKFDKFETESAQLVKEKLLDGNKNFGGAAVTIPLKLDIMQYMDELTDAAKVIGAVNTVIPLGNKKFKGDNTDWLGIRNALINNGVPEYVGHTAGLVIGAGGTSRAALYALHSLGCKKIFIINRTTSKLKPLIESLPSEFNIIGIESTKSIEEIKEHVGVAVSCVPADKPLDDELLSKLERFLVKGAHAAFVPTLLEAAYKPSVTPVMTISQDKYQWHVVPGSQMLVHQGVAQFEKWTGFKGPFKAIFDAVTKE"}]}