{"ymdb_id":"YMDB00732","created_at":"2011-05-29T18:47:40.000Z","updated_at":"2016-09-08T18:35:50.000Z","name":"3-oxoicosanoyl-CoA","cas":null,"state":null,"melting_point":null,"description":"3-Oxoicosanoyl-CoA is a coenzyme A derivative of 3-oxoicosanoate. Fatty acids must be activated with CoA before any chemical modification can be applied. Also fatty acid metabolic intermediates will also exists as CoA derivatives until the CoA is enzymatically cleaved. The fatty acid group is linked to the terminal thoil moiety of CoA.","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":"endoplasmic reticulum","synthesis_reference":null,"chebi_id":"52327","hmdb_id":null,"kegg_id":null,"pubchem_id":null,"cs_id":"21866048","foodb_id":null,"wikipedia_link":null,"biocyc_id":null,"iupac":"{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxoicosanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid","traditional_iupac":"3-keto-C20-coa","logp":"0.615708917439684","pka":"1.8334045156149257","alogps_solubility":"9.49e-01 g/l","alogps_logp":"2.93","alogps_logs":"-3.05","acceptor_count":"18","donor_count":"9","rotatable_bond_count":"38","polar_surface_area":"380.6999999999999","refractivity":"255.7451","polarizability":"109.15146963261273","formal_charge":"0","physiological_charge":"-4","pka_strongest_basic":"4.946041888096896","pka_strongest_acidic":"0.8252479623287816","bioavailability":"0","number_of_rings":"3","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"1","synonyms":["3-keto-C20-CoA","3-ketoeicosanoyl-CoA","3-ketoeicosanoyl-coenzyme A","3-ketoicosanoyl-CoA","3-ketoicosanoyl-coenzyme A","3-oxoeicosanoyl-CoA","3-oxoeicosanoyl-coenzyme A","3-oxoicosanoyl-coenzyme A"],"pathways":[{"name":"Biosynthesis of unsaturated fatty acids","kegg_map_id":"01040"},{"name":"Biosynthesis of unsaturated fatty acids (tetracosanoyl-CoA)","kegg_map_id":null},{"name":"Biosynthesis of unsaturated fatty acids (docosanoyl)","kegg_map_id":null},{"name":"Biosynthesis of unsaturated fatty acids (icosanoyl)","kegg_map_id":null}],"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."},{"pubmed_id":12087109,"citation":"Han, G., Gable, K., Kohlwein, S. D., Beaudoin, F., Napier, J. A., Dunn, T. M. (2002). \"The Saccharomyces cerevisiae YBR159w gene encodes the 3-ketoreductase of the microsomal fatty acid elongase.\" J Biol Chem 277:35440-35449."}],"proteins":[{"created_at":"2011-05-24T21:48:56.000Z","updated_at":"2011-07-22T17:54:52.000Z","name":"Elongation of fatty acids protein 1","uniprot_id":"P39540","uniprot_name":"ELO1_YEAST","enzyme":true,"transporter":false,"gene_name":"ELO1","num_residues":310,"molecular_weight":"36233.60156","theoretical_pi":"9.69","general_function":"Involved in fatty acid elongase activity","specific_function":"May be a membrane bound enzyme involved in the highly specific elongation of saturated 14-carbon fatty acids (14:0) to 16-carbon species (16:0)","reactions":[{"id":1499,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1501,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1503,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2385,"direction":"\u003e","locations":"Membrane; Multi-pass membrane protein (Potential); Multi-pass membrane protein; Multi-pass membrane protein (Probable)","altext":"Acyl-CoA + malonyl-CoA = 3-oxoacyl-CoA + CoA + CO(2).","export":false,"pw_reaction_id":null,"source":null},{"id":3865,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006386","source":"Smpdb"},{"id":3866,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006396","source":"Smpdb"},{"id":3867,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006400","source":"Smpdb"},{"id":3868,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006392","source":"Smpdb"},{"id":3869,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006404","source":"Smpdb"},{"id":3870,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006412","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"64-84;101-121;187-207;235-255;272-292","pdb_id":null,"cellular_location":"Membrane; Multi-pass membrane protein (Potential)","genbank_gene_id":"X77688","genbank_protein_id":"547599","gene_card_id":"ELO1","chromosome_location":"chromosome 10","locus":"YJL196C","synonyms":[],"enzyme_classes":[],"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":" Not Available"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"ELO","identifier":"PF01151"}],"pathways":[{"name":"Biosynthesis of unsaturated fatty 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reductase","uniprot_id":"P35731","uniprot_name":"FABG_YEAST","enzyme":true,"transporter":false,"gene_name":"OAR1","num_residues":278,"molecular_weight":"31183.69922","theoretical_pi":"9.15","general_function":"Involved in oxidoreductase activity","specific_function":"Involved in biosynthesis of fatty acids in mitochondria","reactions":[{"id":2407,"direction":"\u003e","locations":"Mitochondrion","altext":"(3R)-3-hydroxyacyl-[acyl-carrier-protein] + NADP(+) = 3-oxoacyl-[acyl-carrier-protein] + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":3872,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006388","source":"Smpdb"},{"id":3873,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006397","source":"Smpdb"},{"id":3874,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006393","source":"Smpdb"},{"id":3875,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006401","source":"Smpdb"},{"id":3876,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006405","source":"Smpdb"},{"id":3877,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006413","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Mitochondrion","genbank_gene_id":"X75781","genbank_protein_id":"433642","gene_card_id":"OAR1","chromosome_location":"chromosome 11","locus":"YKL055C","synonyms":["3-ketoacyl-acyl carrier protein reductase"],"enzyme_classes":["1.1.1.100"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" oxidation reduction"}],"pfams":[{"name":"adh_short","identifier":"PF00106"}],"pathways":[{"name":"Fatty acid biosynthesis","kegg_map_id":"00061"},{"name":"Biosynthesis of unsaturated fatty 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reductase","uniprot_id":"P38286","uniprot_name":"MKAR_YEAST","enzyme":true,"transporter":false,"gene_name":"IFA38","num_residues":347,"molecular_weight":"38707.80078","theoretical_pi":"10.01","general_function":"Involved in oxidoreductase activity","specific_function":"Component of the microsomal membrane bound fatty acid elongation system, which produces the 26-carbon very long-chain fatty acids (VLCFA) from palmitate. Catalyzes the reduction of the 3-ketoacyl-CoA intermediate that is formed in each cycle of fatty acid elongation. VLCFAs serve as precursors for ceramide and sphingolipids","reactions":[{"id":1741,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1742,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1743,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1744,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1745,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1746,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1747,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2810,"direction":"\u003e","locations":"Endoplasmic reticulum membrane; Single-pass membrane protein (Potential)","altext":"3-hydroxyacyl-CoA + NADP(+) = 3-oxoacyl-CoA + NADPH.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"20-40","pdb_id":null,"cellular_location":"Endoplasmic reticulum membrane; Single-pass membrane protein (Potential)","genbank_gene_id":"AY557868","genbank_protein_id":"45269627","gene_card_id":"IFA38","chromosome_location":"chromosome 2","locus":"YBR159W","synonyms":["3-ketoreductase","KAR","Microsomal beta-keto-reductase"],"enzyme_classes":["1.1.1.-"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" oxidation reduction"}],"pfams":[{"name":"adh_short","identifier":"PF00106"}],"pathways":[],"gene_sequence":"ATGACTTTTATGCAACAGCTTCAAGAGGCTGGGGAAAGATTTAGGTGTATCAATGGTCTTTTATGGGTTGTTTTTGGGCTTGGTGTCTTAAAATGTACAACGTTATCACTTAGATTTTTAGCTCTTATTTTTGATCTTTTTTTACTACCAGCAGTCAATTTCGACAAGTATGGTGCTAAAACTGGTAAATACTGTGCTATCACTGGTGCAAGTGACGGTATTGGTAAAGAATTTGCTAGACAAATGGCGAAACGTGGCTTCAACTTGGTATTGATCTCGAGAACGCAATCTAAATTGGAGGCTTTACAAAAAGAACTAGAAGATCAACATCATGTCGTTGTAAAGATTCTAGCCATTGACATTGCGGAGGATAAAGAATCCAACTATGAATCCATTAAGGAATTGTGTGCGCAGTTACCAATCACCGTTTTGGTCAATAATGTTGGTCAATCACACTCCATTCCTGTTCCATTTTTGGAAACAGAAGAGAAGGAGCTTAGAAATATTATCACTATCAATAACACTGCTACATTATTAATTACACAAATCATTGCACCAAAGATTGTGGAAACTGTGAAAGCTGAAAACAAGAAGTCGGGTACTCGTGGTTTGATCTTAACCATGGGCTCATTTGGTGGTCTGATTCCCACCCCACTTTTGGCTACATACAGTGGTTCGAAATCATTCTTACAAGGTTGGTCTAACTCTTTGGCTGGGGAATTATCTAAAGATGCTATCGATGTTGAATTAATCATTTCATATTTGGTCACTAGCTCGATGTCTAAAATCAGAAGATCATCTTTAATGATCCCAAATCCACAACAGTTTGTAAAATCCACTTTAAGAAGCGTTGGCAGACGCTGCGGCTCTCAAGAAAGATACGCTACTATGACCCCTTACTGGGCGCACGCAGTGTATCAATTTGTAATTACAGAGACCTTTGGCGTTTACTCTAAGATTGTTAACTCCATTAATTATTCCTTCCATAAATCTATCAGAATTAGAGCCTTAAAAAAAGCCGCAAGACAGGTTAAAAAGGAATAG","protein_sequence":"MTFMQQLQEAGERFRCINGLLWVVFGLGVLKCTTLSLRFLALIFDLFLLPAVNFDKYGAKTGKYCAITGASDGIGKEFARQMAKRGFNLVLISRTQSKLEALQKELEDQHHVVVKILAIDIAEDKESNYESIKELCAQLPITVLVNNVGQSHSIPVPFLETEEKELRNIITINNTATLLITQIIAPKIVETVKAENKKSGTRGLILTMGSFGGLIPTPLLATYSGSKSFLQGWSNSLAGELSKDAIDVELIISYLVTSSMSKIRRSSLMIPNPQQFVKSTLRSVGRRCGSQERYATMTPYWAHAVYQFVITETFGVYSKIVNSINYSFHKSIRIRALKKAARQVKKE"}]}