{"ymdb_id":"YMDB00246","created_at":"2011-05-29T17:58:09.000Z","updated_at":"2016-09-08T18:35:14.000Z","name":"S-Lactoylglutathione","cas":"25138-66-3","state":"Solid","melting_point":"","description":"S-Lactoylglutathione is an interemdiate in detoxification of methylglyoxal (2-oxopropanal). Methylglyoxal is converted to S-Lactoylglutathione by the glutathione dependant enzyme lactoylglutathione lyase [EC 4.4.1.5]. S-Lactoylglutathione is then rearrange to D-Lactic acid and glutathione by the enzyme hydroxyacylglutathione hydrolase [EC 3.1.2.6]. [PMID: 6343368]\n","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"mitochondrion;cytoplasm","synthesis_reference":"Liu, Yan; Hama, Hideki; Fujita, Yasuya; Kondo, Akihiko; Inoue, Yoshiharu; Kimura, Akira; Fu Production of S-lactoylglutathione by high activity whole cell biocatalysts prepared by permeabilization of recombinant Saccharomyces cerevisiae with alcohols. ","chebi_id":"15694","hmdb_id":"HMDB01066","kegg_id":"C03451","pubchem_id":"119450","cs_id":null,"foodb_id":null,"wikipedia_link":null,"biocyc_id":"S-LACTOYL-GLUTATHIONE","iupac":"(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(2R)-2-hydroxypropanoyl]sulfanyl}ethyl]carbamoyl}butanoic acid","traditional_iupac":"S-lactoylglutathione","logp":"-5.369701498472575","pka":"3.343963632400796","alogps_solubility":"7.55e+00 g/l","alogps_logp":"-2.88","alogps_logs":"-1.70","acceptor_count":"9","donor_count":"6","rotatable_bond_count":"12","polar_surface_area":"196.12","refractivity":"84.7788","polarizability":"36.011916776462776","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"9.311036181503438","pka_strongest_acidic":"1.7414579722275407","bioavailability":"0","number_of_rings":"0","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["(R)-S-lactoylglutathione","D-lactoylglutathione","delta-lactoylglutathione","n-(n-l-gamma-glutamyl-S-(2-hydroxy-1-oxopropyl)-l-cysteinyl)-glycine","S-[(2R)-2-hydroxypropanoyl]-gamma-L-glutamyl-L-cysteinylglycine","S-D-lactoyl-glutathione","S-D-lactoylglutathione","S-delta-lactoyl-glutathione","S-delta-lactoylglutathione","S-lactate glutathione","S-lactateglutathione","S-lactoyl-glutathione","S-lactylglutathione"],"pathways":[{"name":"Pyruvate metabolism","kegg_map_id":"00620"}],"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":3908097,"citation":"Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). \"Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae.\" Eur J Biochem 153:243-247."},{"pubmed_id":6343368,"citation":"Penninckx, M. J., Jaspers, C. J., Legrain, M. J. (1983). \"The glutathione-dependent glyoxalase pathway in the yeast Saccharomyces cerevisiae.\" J Biol Chem 258:6030-6036."}],"proteins":[{"created_at":"2011-05-27T02:56:34.000Z","updated_at":"2011-05-27T15:01:19.000Z","name":"Hydroxyacylglutathione hydrolase, cytoplasmic isozyme","uniprot_id":"Q05584","uniprot_name":"GLO2_YEAST","enzyme":true,"transporter":false,"gene_name":"GLO2","num_residues":274,"molecular_weight":"31326.30078","theoretical_pi":"6.11","general_function":"Involved in hydrolase activity","specific_function":"Thiolesterase that catalyzes the hydrolysis of S-D- lactoyl-glutathione to form glutathione and D-lactic acid","reactions":[{"id":1644,"direction":"\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2700,"direction":"\u003e","locations":"Mitochondrion matrix;Cytoplasm","altext":"S-(2-hydroxyacyl)glutathione + H(2)O = glutathione + a 2-hydroxy carboxylate.","export":false,"pw_reaction_id":null,"source":null},{"id":14118,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006549","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasm","genbank_gene_id":"U51030","genbank_protein_id":"1230643","gene_card_id":"GLO2","chromosome_location":"chromosome 4","locus":"YDR272W","synonyms":["Glyoxalase II","Glx II"],"enzyme_classes":["3.1.2.6"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" hydrolase activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Lactamase_B","identifier":"PF00753"}],"pathways":[{"name":"Pyruvate metabolism","kegg_map_id":"00620"}],"gene_sequence":"ATGCAGGTTAAATCGATTAAAATGAGATGGGAGTCTGGTGGTGTTAATTACTGCTATCTATTGTCCGACAGTAAAAATAAAAAATCGTGGCTAATCGATCCAGCAGAGCCTCCTGAGGTTCTGCCAGAGTTGACTGAGGATGAGAAAATAAGTGTTGAAGCAATTGTTAATACACATCACCATTATGACCATGCAGATGGTAACGCTGATATCTTGAAGTATTTAAAAGAGAAAAATCCAACTTCAAAAGTTGAGGTTATAGGAGGGTCAAAGGACTGCCCAAAGGTTACGATAATTCCGGAGAATTTGAAAAAGTTACACCTAGGTGACTTAGAGATTACTTGTATTAGGACGCCCTGCCATACCAGAGACTCTATCTGTTATTATGTGAAAGATCCAACAACAGATGAGCGCTGCATTTTTACTGGCGATACACTATTTACCGCTGGTTGCGGTAGGTTTTTTGAGGGTACAGGCGAAGAAATGGATATAGCTCTGAACAATTCTATCTTAGAAACTGTGGGCAGGCAGAACTGGAGTAAAACGAGGGTTTATCCAGGACACGAATACACAAGTGATAATGTAAAGTTTGTTCGTAAGATTTACCCGCAAGTTGGTGAAAATAAAGCATTGGATGAGTTAGAACAATTCTGCTCCAAGCATGAAGTCACAGCAGGGCGGTTCACTTTGAAAGATGAGGTAGAATTTAATCCATTCATGAGATTAGAAGATCCAAAGGTCCAAAAAGCTGCCGGAGATACGAATAATTCATGGGACAGAGCTCAAATTATGGATAAATTGAGAGCTATGAAAAACCGTATGTAG","protein_sequence":"MQVKSIKMRWESGGVNYCYLLSDSKNKKSWLIDPAEPPEVLPELTEDEKISVEAIVNTHHHYDHADGNADILKYLKEKNPTSKVEVIGGSKDCPKVTIIPENLKKLHLGDLEITCIRTPCHTRDSICYYVKDPTTDERCIFTGDTLFTAGCGRFFEGTGEEMDIALNNSILETVGRQNWSKTRVYPGHEYTSDNVKFVRKIYPQVGENKALDELEQFCSKHEVTAGRFTLKDEVEFNPFMRLEDPKVQKAAGDTNNSWDRAQIMDKLRAMKNRM"},{"created_at":"2011-05-27T03:01:53.000Z","updated_at":"2011-05-29T05:06:37.000Z","name":"Lactoylglutathione lyase","uniprot_id":"P50107","uniprot_name":"LGUL_YEAST","enzyme":true,"transporter":false,"gene_name":"GLO1","num_residues":326,"molecular_weight":"37208.69922","theoretical_pi":"6.84","general_function":"Involved in lactoylglutathione lyase activity","specific_function":"Catalyzes the conversion of hemimercaptal, formed from methylglyoxal and glutathione, to S-lactoylglutathione","reactions":[{"id":1710,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2704,"direction":"\u003e","locations":null,"altext":"(R)-S-lactoylglutathione = glutathione + methylglyoxal.","export":false,"pw_reaction_id":null,"source":null},{"id":14117,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006548","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"AJ297938","genbank_protein_id":"11182130","gene_card_id":"GLO1","chromosome_location":"chromosome 13","locus":"YML004C","synonyms":["Aldoketomutase","Glyoxalase I","Glx I","Ketone-aldehyde mutase","Methylglyoxalase","S-D-lactoylglutathione methylglyoxal lyase"],"enzyme_classes":["4.4.1.5"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" lyase activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" ion binding"},{"category":"Function","description":" cation binding"},{"category":"Function","description":" metal ion binding"},{"category":"Function","description":" carbon-sulfur lyase activity"},{"category":"Function","description":" lactoylglutathione lyase activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Glyoxalase","identifier":"PF00903"}],"pathways":[{"name":"Pyruvate metabolism","kegg_map_id":"00620"}],"gene_sequence":"ATGTCCACTGATAGTACACGCTATCCAATTCAGATTGAGAAAGCCTCGAATGATCCAACCCTTCTGCTTAATCACACATGTTTAAGAGTCAAGGATCCAGCAAGGGCTGTTAAGTTCTACACCGAACACTTCGGTATGAAGCTATTAAGCAGAAAGGATTTTGAAGAAGCAAAATTTAGCTTGTACTTTTTAAGCTTTCCAAAAGACGACATACCCAAAAATAAGAATGGAGAGCCTGATGTTTTTAGCGCACACGGTGTCTTAGAACTAACTCACAATTGGGGTACTGAAAAAAACCCAGACTACAAGATCAACAACGGGAATGAGGAACCTCATCGTGGATTTGGGCACATCTGTTTTTCTGTATCCGATATCAATAAAACCTGCGAAGAGCTAGAATCTCAGGGTGTCAAATTCAAGAAGAGACTCTCTGAAGGAAGACAGAAGGACATTGCGTTTGCTTTAGACCCTGATGGATACTGGATTGAGTTGATCACATATTCTAGAGAGGGTCAGGAATACCCAAAGGGCTCAGTAGGTAACAAGTTCAATCATACCATGATTCGTATTAAAAACCCAACCCGGTCTTTAGAATTCTACCAGAATGTGTTGGGCATGAAATTATTAAGAACTAGTGAGCACGAAAGTGCAAAATTTACGTTATACTTTCTTGGTTATGGCGTTCCAAAGACCGACAGCGTTTTTTCATGTGAAAGTGTGTTGGAGTTAACTCATAATTGGGGAACTGAGAATGATCCAAACTTCCACTATCATAACGGTAACTCAGAGCCCCAGGGTTATGGTCACATCTGCATAAGTTGCGATGACGCTGGCGCCCTTTGTAAAGAAATTGAAGTGAAATACGGCGATAAGATCCAATGGTCTCCTAAATTTAACCAAGGCAGAATGAAGAATATTGCCTTTTTGAAGGATCCTGATGGTTATTCCATTGAAGTCGTTCCTTATGGTTTGATTGCCTAA","protein_sequence":"MSTDSTRYPIQIEKASNDPTLLLNHTCLRVKDPARTVKFYTEHFGMKLLSRKDFEEAKFSLYFLSFPKDDIPKNKNGEPDVFSAHGVLELTHNWGTEKNPDYKINNGNEEPHRGFGHICFSVSDINKTCEELESQGVKFKKRLSEGRQKDIAFALGPDGYWIELITYSREGQEYPKGSVGNKFNHTMIRIKNPTRSLEFYQNVLGMKLLRTSEHESAKFTLYFLGYGVPKTDSVFSCESVLELTHNWGTENDPNFHYHNGNSEPQGYGHICISCDDAGALCKEIEVKYGDKIQWSPKFNQGRMKNIAFLKDPDGYSIEVVPHGLIA"},{"created_at":"2011-05-27T03:05:12.000Z","updated_at":"2011-05-27T15:01:19.000Z","name":"Hydroxyacylglutathione hydrolase, mitochondrial","uniprot_id":"Q12320","uniprot_name":"GLO4_YEAST","enzyme":true,"transporter":false,"gene_name":"GLO4","num_residues":285,"molecular_weight":"32338.59961","theoretical_pi":"7.52","general_function":"Involved in hydrolase activity","specific_function":"Thiolesterase that catalyzes the hydrolysis of S-D- lactoyl-glutathione to form glutathione and D-lactic acid","reactions":[{"id":1644,"direction":"\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2700,"direction":"\u003e","locations":"Mitochondrion matrix;Cytoplasm","altext":"S-(2-hydroxyacyl)glutathione + H(2)O = glutathione + a 2-hydroxy carboxylate.","export":false,"pw_reaction_id":null,"source":null},{"id":14118,"direction":"\u003c\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006549","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Mitochondrion matrix","genbank_gene_id":"AY692965","genbank_protein_id":"51013381","gene_card_id":"GLO4","chromosome_location":"chromosome 15","locus":"YOR040W","synonyms":["Glyoxalase II","Glx II"],"enzyme_classes":["3.1.2.6"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" hydrolase activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Lactamase_B","identifier":"PF00753"}],"pathways":[{"name":"Pyruvate metabolism","kegg_map_id":"00620"}],"gene_sequence":"ATGAAGTTTTTACTGCAGCAAATAAGAAATATGCATGTTAAGCCTATAAAAATGCGATGGTTGACAGGTGGTGTCAATTATAGTTATTTACTAAGCACTGAAGACAGGAGAAACTCATGGCTGATTGACCCTGCAGAACCACTTGAGGTGTCGCCAAAATTAAGCGCCGAAGAGAAAAAAAGTATTGATGCTATTGTCAATACACATCACCATTATGACCATTCGGGGGGGAACCTAGCGCTTTATAGTATCTTGTGCCAAGAAAACTCAGGTCACGATATTAAAATAATTGGTGGATCTAAGTCCTCCCCGGGTGTCACTGAAGTACCCGATAATTTGCAGCAGTATCACTTGGGTAACTTAAGAGTAACATGTATTAGGACTCCATGCCATACAAAAGATTCCATATGCTATTATATCAAAGATTTAGAAACAGGTGAGCAGTGCATCTTCACAGGCGACACTTTATTCATTGCCGGTTGTGGGAGGTTTTTCGAGGGCACAGGAAGAGATATGGACATGGCCTTAAACCAGATAATGTTAAGGGCTGTTGGTGAGACGAACTGGAATAAGGTTAAAATATACCCTGGTCATGAGTACACCAAAGGCAATGTTAGCTTTATCAGAGCAAAAATCTATTCCGATATAGGGCAGAACAAGGAGTTTGATGCGTTGGAACAGTATTGCAAATCTAACGAGTGCACCACCGGTCACTTCACCCTGAGAGATGAACTAGGTTATAACCCATTCATGAGATTGGATGATCGTGCCGTTAGACTAGCAGTCGGCGATACTGCTGGGACTTATCCCAGATCCGTAGTGATGCAAGAGTTAAGAAAGCTTAAAAACGCTATGTAA","protein_sequence":"MKFLLQQIRNMHVKPIKMRWLTGGVNYSYLLSTEDRRNSWLIDPAEPLEVSPKLSAEEKKSIDAIVNTHHHYDHSGGNLALYSILCQENSGHDIKIIGGSKSSPGVTEVPDNLQQYHLGNLRVTCIRTPCHTKDSICYYIKDLETGEQCIFTGDTLFIAGCGRFFEGTGRDMDMALNQIMLRAVGETNWNKVKIYPGHEYTKGNVSFIRAKIYSDIGQNKEFDALEQYCKSNECTTGHFTLRDELGYNPFMRLDDRAVRLAVGDTAGTYPRSVVMQELRKLKNAM"}]}