{"ymdb_id":"YMDB00978","created_at":"2011-06-04T18:49:15.000Z","updated_at":"2016-09-08T18:36:06.000Z","name":"(2S,3S)-2-Methylcitric acid","cas":"6061-96-7","state":"Solid","melting_point":"","description":"(2S,3S)-2-Methylcitric acid is one of the four methylcitric acid (MCA) stereoisomers. MCA is formed by condensation of accumulated propionyl-CoA and oxalacetate by the enzyme si-citrate synthase [EC 4.1.3.7].","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"mitochondrion","synthesis_reference":"Ewering, Christian; Braemer, Christian Oliver; Steinbuechel, Alexander.  Production of 2-methylcitric acid by a recombinant Ralstonia eutropha strain.    PCT Int. Appl.  (2007),     30pp.  CODEN: PIXXD2  WO  2007101866  A2  20070913  CAN 147:363646  AN 20","chebi_id":"50948","hmdb_id":"HMDB00379","kegg_id":"","pubchem_id":"515","cs_id":"24534242","foodb_id":null,"wikipedia_link":null,"biocyc_id":null,"iupac":"(1S,2S)-2-hydroxy-1-methylpropane-1,2,3-tricarboxylic acid","traditional_iupac":"(2S,3S)-2-methylcitric acid","logp":"-0.7797011736666666","pka":"4.7852796669207125","alogps_solubility":"1.75e+02 g/l","alogps_logp":"-0.89","alogps_logs":"-0.07","acceptor_count":"7","donor_count":"4","rotatable_bond_count":"5","polar_surface_area":"132.13000000000002","refractivity":"40.1984","polarizability":"17.326490002168775","formal_charge":"0","physiological_charge":"-3","pka_strongest_basic":"-4.260390633991254","pka_strongest_acidic":"3.18324322639043","bioavailability":"1","number_of_rings":"0","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["(2S,3S)-2-methylcitrate","2-hydroxy-1,2,3-butanetricarboxylic acid","2-hydroxybutane-1,2,3-tricarboxylate","2-hydroxybutane-1,2,3-tricarboxylic acid","2-methylcitrate","2-methylcitric acid"],"pathways":[],"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":7912143,"citation":"Pronk, J. T., van der Linden-Beuman, A., Verduyn, C., Scheffers, W. A., van Dijken, J. P. (1994). \"Propionate metabolism in Saccharomyces cerevisiae: implications for the metabolon hypothesis.\" Microbiology 140 ( Pt 4):717-722."},{"pubmed_id":9579066,"citation":"Gerike, U., Hough, D. W., Russell, N. J., Dyall-Smith, M. L., Danson, M. J. (1998). \"Citrate synthase and 2-methylcitrate synthase: structural, functional and evolutionary relationships.\" Microbiology 144 ( Pt 4):929-935."},{"pubmed_id":16332871,"citation":"Singh, J., Kumar, D., Ramakrishnan, N., Singhal, V., Jervis, J., Garst, J. F., Slaughter, S. M., DeSantis, A. M., Potts, M., Helm, R. F. (2005). \"Transcriptional response of Saccharomyces cerevisiae to desiccation and rehydration.\" Appl Environ Microbiol 71:8752-8763."}],"proteins":[{"created_at":"2011-05-26T16:05:55.000Z","updated_at":"2011-07-22T17:54:31.000Z","name":"Citrate synthase 3","uniprot_id":"P43635","uniprot_name":"CISY3_YEAST","enzyme":true,"transporter":false,"gene_name":"CIT3","num_residues":486,"molecular_weight":"53810.69922","theoretical_pi":"8.79","general_function":"Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer","specific_function":"Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA","reactions":[{"id":1151,"direction":"\u003e","locations":"mitochondrion","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1411,"direction":"\u003e","locations":"mitochondrion;peroxisome","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2408,"direction":"\u003e","locations":"Peroxisome;Mitochondrion matrix","altext":"Acetyl-CoA + H(2)O + oxaloacetate = citrate + CoA.","export":false,"pw_reaction_id":null,"source":null},{"id":2409,"direction":"\u003e","locations":null,"altext":"propanoyl-CoA + H2O + oxaloacetate = (2R,3S)-2-hydroxybutane-1,2,3-tricarboxylate + CoA","export":false,"pw_reaction_id":null,"source":null},{"id":3697,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R003280","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"U31900","genbank_protein_id":"939735","gene_card_id":"CIT3","chromosome_location":"chromosome 16","locus":"YPR001W","synonyms":[],"enzyme_classes":["2.3.3.1","2.3.3.5"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring acyl groups"},{"category":"Process","description":" tricarboxylic acid cycle"},{"category":"Process","description":" cellular carbohydrate metabolic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" primary metabolic process"},{"category":"Process","description":" carbohydrate metabolic process"},{"category":"Process","description":" cofactor metabolic process"},{"category":"Process","description":" coenzyme metabolic process"},{"category":"Process","description":" acetyl-CoA metabolic process"},{"category":"Process","description":" acetyl-CoA catabolic process"}],"pfams":[{"name":"Citrate_synt","identifier":"PF00285"}],"pathways":[{"name":"Citrate cycle (TCA cycle)","kegg_map_id":"00020"},{"name":"Glyoxylate and dicarboxylate metabolism","kegg_map_id":"00630"},{"name":"Citric Acid Cycle 1434561204","kegg_map_id":null},{"name":"TCA Cycle","kegg_map_id":null}],"gene_sequence":"ATGGTACAAAGGCTTCTACCGGGCGCACATATATGCAGAAGGTCCTTCAATTCGTCTGCAATTATAAAGTCTTCTGCATTGACTCTCAAGGAAGCATTAGAAAACGTGATACCTAAGAAAAGAGATGCTGTGAAGAAATTGAAGGCCTGTTATGGCAGCACGTTTGTCGGACCGATTACCATTTCATCAGTTCTAGGTGGGATGAGAGGTAATCAGTCAATGTTTTGGCAAGGAACATCATTAGATCCCGAACATGGCATTAAATTTCAAGGTTTAACGATTGAAGAATGTCAAAATAGATTACCTAATACAGGTATTGATGGCGATAATTTCCTGCCAGAATCAATGTTATGGCTGTTGATGACAGGTGGTGTGCCAACTTTCCAGCAAGCTGCTTCTTTCAGGAAAGAATTGGCTATTCGTGGAAGGAAATTGCCACATTATACAGAGAAAGTTTTGTCAAGTTTACCCAAAGATATGCACCCTATGACCCAACTTGCAATTGGTTTAGCATCAATGAACAAAGGATCCCTCTTTGCTACAAACTACCAAAAGGGCCTCATAGGAAAGATGGAATTTTGGAAAGATACTCTTGAAGATTCGCTAAATTTAATTGCTTCACTCCCGCTGCTGACTGGGAGAATTTATTCGAACATTACAAATGAGGGACACCCATTAGGTCAATATAGTGAGGAGGTGGATTGGTGTACAAACATATGTTCCCTGCTCGGCATGACAAATGGAACGAACTCTTCTAATACATGCAACCTTACTTCCCAGCAATCCCTGGACTTCATAAACTTGATGCGGTTATATACCGGTATACATGTAGACCATGAAGGTGGTAATGTTTCTGCTCACACCACCCACTTGGTTGGAAGTGCGTTGAGTGACCCGTATCTCAGCTATTCATCTGGAATAATGGGATTAGCGGGTCCTTTGCATGGGTTAGCAGCACAAGAAGTAGTAAGGTTTCTCATAGAGATGAACTCTAATATTTCCAGCATTGCACGAGAACAAGAAATCAAAGATTATCTTTGGAAAATTTTGAATTCAAACCGTGTGATCCCCGGTTATGGGCACGCAGTTTTGCGTAAACCGGATCCTCGATTTACAGCAATGCTTGAATTTGCGCAAAAGAGGCCTATTGAATTTGAGAACGACAAGAACGTTTTGTTGATGCAAAAATTGGCAGAAATAGCGCCTAAGGTTTTGTTGGAACACGGAAAGAGTAAGAATCCATTTCCCAATGTTGACTCTGCATCGGGGATTTTGTTTTATCATTATGGAATCAGGGAATTATTATTCTTTACCGTCATTTTTGGGTGTTCAAGGGCCATGGGACCCTTGACACAACTTGTTTGGGATCGCATTCTAGGTTTACCAATTGAAAGGCCCAAGAGTTTGAACTTGGAGGGTCTGGAAGCACTTACCAAAGCAAGCAATGTTAACAAGTTGTAA","protein_sequence":"MVQRLLPGAHICRRSFNSSAIIKSSALTLKEALENVIPKKRDAVKKLKACYGSTFVGPITISSVLGGMRGNQSMFWQGTSLDPEHGIKFQGLTIEECQNRLPNTGIDGDNFLPESMLWLLMTGGVPTFQQAASFRKELAIRGRKLPHYTEKVLSSLPKDMHPMTQLAIGLASMNKGSLFATNYQKGLIGKMEFWKDTLEDSLNLIASLPLLTGRIYSNITNEGHPLGQYSEEVDWCTNICSLLGMTNGTNSSNTCNLTSQQSLDFINLMRLYTGIHVDHEGGNVSAHTTHLVGSALSDPYLSYSSGIMGLAGPLHGLAAQEVVRFLIEMNSNISSIAREQEIKDYLWKILNSNRVIPGYGHAVLRKPDPRFTAMLEFAQKRPIEFENDKNVLLMQKLAEIAPKVLLEHGKSKNPFPNVDSASGILFYHYGIRELLFFTVIFGCSRAMGPLTQLVWDRILGLPIERPKSLNLEGLEALTKASNVNKL"},{"created_at":"2011-05-27T07:00:12.000Z","updated_at":"2011-07-22T17:53:56.000Z","name":"Probable 2-methylcitrate dehydratase","uniprot_id":"Q12428","uniprot_name":"PRPD_YEAST","enzyme":true,"transporter":false,"gene_name":"PDH1","num_residues":516,"molecular_weight":"57683.10156","theoretical_pi":"9.51","general_function":"Involved in 2-methylcitrate dehydratase activity","specific_function":"Catalyzes the dehydration of 2-methylcitrate to 2- methyl-cis-aconitate","reactions":[{"id":1246,"direction":"\u003c\u003e","locations":"mitochondrion","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2797,"direction":"\u003e","locations":null,"altext":"(2S,3S)-2-hydroxybutane-1,2,3-tricarboxylate = (Z)-but-2-ene-1,2,3-tricarboxylate + H(2)O.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"U31900","genbank_protein_id":"939736","gene_card_id":"PDH1","chromosome_location":"chromosome 16","locus":"YPR002W","synonyms":[],"enzyme_classes":["4.2.1.79"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" 2 iron, 2 sulfur cluster binding"},{"category":"Function","description":" 2-methylcitrate dehydratase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" lyase activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" metal cluster binding"},{"category":"Function","description":" iron-sulfur cluster binding"},{"category":"Function","description":" carbon-oxygen lyase activity"},{"category":"Function","description":" hydro-lyase activity"},{"category":"Process","description":" carboxylic acid metabolic process"},{"category":"Process","description":" monocarboxylic acid metabolic process"},{"category":"Process","description":" propionate metabolic process"},{"category":"Process","description":" propionate catabolic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" propionate catabolic process, 2-methylcitrate cycle"},{"category":"Process","description":" cellular metabolic process"},{"category":"Process","description":" organic acid metabolic process"},{"category":"Process","description":" oxoacid metabolic process"}],"pfams":[{"name":"MmgE_PrpD","identifier":"PF03972"}],"pathways":[{"name":"Propanoate metabolism","kegg_map_id":"00640"}],"gene_sequence":"ATGTTTTTAGCCAAAAATCTAAAAAATAATAAAATCAAGGTATGCTTGCCTAAAAAGAAATTTGCTGCGCTGAGTACAGCGTCTATACAAACTAATGAAAGACCAAATCCAGATAAGGTTTTGAAGGACATCGCGAAATATGTCCATGAAACCCCATTAAAATCATCTTTGGCTCTAGATACAGCACGACTCTGTTTCCTTGATACTCTAGGCTGTGGCTTGGCGGCTTTGAAATTTAAGCAGGCTCAAAATATTATTAAACCAATTGTGCCAGGAACAATAGTTCCCAGTGGAACAAAAATATTGGGCACATCTTACGTTATGGATCCAGTGAAGGGAGCTTTTGCCATTGGTACTCTAATACGTTGGTTAGATTACAATGACTGCTGGTTAGCTGCCGAGTGGGGGCACCCATCAGATAACCTTGGGGGAATTTTAGCTGTCGCGGATCACTTGTCCAGATTAAACAAGGCTACCCACGGAAAGAATGGAAAACAGTTTCTTGTTAAAGACGTATTAGAGGCAATGATTAAAGCGCATGAAATCCAAGGTATTATAGCGCTCGAAAATTCTTTCAATAAAGTAGGTTTAGATCATGTGGTACTCGTGAAAGTAGCAACGGCTGGTGTTGTCTCGAAGATGCTGGGCCTGAGCCAGGAACAAACTATTGAAGCATTGTCACAAGCATTTGTAGACGGTCAATCACTGCGTACTTACCGTCATGCCCCAAATACTGGATCTAGAAAGTCGTGGGCGGCGGGAGATGCAGTTTCGAGGGCTGTAAACTTGGCTTATTTAGTCAAAAATGCTAATGTTGGCACGATACCTTCAGTATTAACAGCTAGAACCTGGGGATTTTATGACGTTTTATTTAAGGGTAAACCTTTTTCATTCCAACAAAGATCAAAATATGATTCCTACGTCATGGAAAACGTTCTGTTCAAGATATCATTTCCTGCCGAATTCCATGCGCAAACTGCTGTAGAAGCTGCTGTAAAAGCATATAGGATTCTTGCCAAACAAGGGAAAACTTTTAAAGATATTAAATCGATCAGAATTAGAACTCAAGAGGCGGCAATGAGGATTATAGATAAATCCGGTCCTCTGTATAATTATGCCGATAGGGATCATTGTATCCAGTACATGATCGCGGTTCCGCTGATTACTGGTAATCTCACAGCTACTGATTATTCGGATGAGGTCGCAAGAAATCCTGAGATCGATAACTTGAGATCGAAAATGTACTGTATCGAAGATACTCATCTCACTCAAAACTATCACGATCCTGATAAAAGGTCGATAGGAAACGCTCTTCTCATAGAGCTGAACGATGGGACGCAGTTGGATGAAATTTTTGTAGAGTACCCTGTTGGTCACAAATTTAGACGAGAGGAAGGAATACCATTACTAATGAATAAATTTCAAAGGCATCTGCGCGAACATTTTGTAGAGAGCCCTGATAAAGTCGACCTTATAATGAAGGTAAGTTCAAAAACAAACTTTTTGAATATGCAAATCGACAAATACATGGATTTGTTTACTGAGGGATGA","protein_sequence":"MFLAKNLKNNKIKVCLPKKKFAALSTASIQTNERPNPDKVLKDIAKYVHETPLKSSLALDTARLCFLDTLGCGLAALKFKQAQNIIKPIVPGTIVPSGTKILGTSYVMDPVKGAFAIGTLIRWLDYNDCWLAAEWGHPSDNLGGILAVADHLSRLNKATHGKNGKQFLVKDVLEAMIKAHEIQGIIALENSFNKVGLDHVVLVKVATAGVVSKMLGLSQEQTIEALSQAFVDGQSLRTYRHAPNTGSRKSWAAGDAVSRAVNLAYLVKNANVGTIPSVLTARTWGFYDVLFKGKPFSFQQRSKYDSYVMENVLFKISFPAEFHAQTAVEAAVKAYRILAKQGKTFKDIKSIRIRTQEAAMRIIDKSGPLYNYADRDHCIQYMIAVPLITGNLTATDYSDEVARNPEIDNLRSKMYCIEDTHLTQNYHDPDKRSIGNALLIELNDGTQLDEIFVEYPVGHKFRREEGIPLLMNKFQRHLREHFVESPDKVDLIMKVSSKTNFLNMQIDKYMDLFTEG"}]}