{"ymdb_id":"YMDB00107","created_at":"2011-05-29T15:57:20.000Z","updated_at":"2016-09-08T18:35:02.000Z","name":"Pyroglutamic acid","cas":"98-79-3","state":"Solid","melting_point":"184.7 oC","description":"Pyroglutamic acid is a cyclized derivative of L-glutamic acid. It is an uncommon amino acid derivative in which the free amino group of glutamic acid cyclizes to form a lactam. It is formed nonenzymatically from glutamate, glutamine, and gamma-glutamylated peptides, but it can also be produced by the action of gamma-glutamylcyclotransferase on an L-amino acid.","experimental_water_solubility":"476 mg/mL at 13 oC [BEILSTEIN]","experimental_logp_hydrophobicity":null,"location":"Cytoplasm","synthesis_reference":"Pumpor, Ksenia; Boettcher, Christoph; Fehn, Susanna; Burger, Klaus. Hexafluoroacetone as protecting and activating reagent: an efficient strategy for activation of pyroglutamic acid and homologs.Heterocycles  (2003),  61  259-269.","chebi_id":"18183","hmdb_id":"HMDB00267","kegg_id":"C01879","pubchem_id":"7405","cs_id":"7127","foodb_id":null,"wikipedia_link":"Pyroglutamic_acid ","biocyc_id":"CPD-589","iupac":"(2S)-5-oxopyrrolidine-2-carboxylic acid","traditional_iupac":"pyroglutamic acid","logp":"-0.8896697023333333","pka":"12.760445138872075","alogps_solubility":"1.51e+02 g/l","alogps_logp":"-1.01","alogps_logs":"0.07","acceptor_count":"3","donor_count":"2","rotatable_bond_count":"1","polar_surface_area":"66.4","refractivity":"28.0878","polarizability":"11.55635110215903","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":"-2.2244398721602403","pka_strongest_acidic":"3.613354339229633","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["(-)-2-Pyrrolidone-5-carboxylate","(-)-2-Pyrrolidone-5-carboxylic acid","(-)-Pyroglutamate","(-)-Pyroglutamic acid","(5S)-2-Oxopyrrolidine-5-carboxylate","(5S)-2-Oxopyrrolidine-5-carboxylic acid","(S)-(-)-2-Pyrrolidone-5-carboxylate","(S)-(-)-2-Pyrrolidone-5-carboxylic acid","(S)-(-)-g-Butyrolactam-g-carboxylate","(S)-(-)-g-Butyrolactam-g-carboxylic acid","(S)-(-)-gamma-Butyrolactam-gamma-carboxylate","(S)-(-)-gamma-Butyrolactam-gamma-carboxylic acid","(S)-2-Pyrrolidone-5-carboxylate","(S)-2-Pyrrolidone-5-carboxylic acid","(S)-5-Oxo-2-pyrrolidinecarboxylate","(S)-5-Oxo-2-pyrrolidinecarboxylic acid","(S)-Pyroglutamate","(S)-Pyroglutamic acid","2-L-Pyrrolidone-5-carboxylate","2-L-Pyrrolidone-5-carboxylic acid","2-Oxopyrrolidine-5(S)-carboxylate","2-Oxopyrrolidine-5(S)-carboxylic acid","2-Pyrrolidinone-5-carboxylate","2-Pyrrolidinone-5-carboxylic acid","5-Carboxy-2-pyrrolidinone","5-L-oxoproline","5-Oxo-L-proline","5-Oxoproline","5-Pyrrolidinone-2-carboxylate","5-Pyrrolidinone-2-carboxylic acid","Glutimate","Glutimic acid","Glutiminate","Glutiminic acid","L-2-Pyrrolidone-5-carboxylate","L-2-Pyrrolidone-5-carboxylic acid","L-5-Carboxy-2-pyrrolidinone","L-5-Oxo-2-pyrrolidinecarboxylate","L-5-Oxo-2-pyrrolidinecarboxylic acid","L-5-Oxoproline","L-Glutamic acid g-lactam","L-Glutimate","L-Glutimic acid","L-Glutiminate","L-Glutiminic acid","L-Pyroglutamate","L-Pyroglutamic acid","L-Pyrrolidinonecarboxylate","L-Pyrrolidinonecarboxylic acid","L-Pyrrolidonecarboxylate","L-Pyrrolidonecarboxylic acid","Oxoproline","Oxopyrrolidinecarboxylate","Oxopyrrolidinecarboxylic acid","Pidolate","Pidolic acid","Pidolidone","Pyroglutamate","Pyroglutamic acid","Pyrrolidinonecarboxylate","Pyrrolidinonecarboxylic acid","Pyrrolidone-5-carboxylate","Pyrrolidone-5-carboxylic acid","Pyrrolidonecarboxylic acid"],"pathways":[{"name":"Glutathione metabolism","kegg_map_id":"00480"}],"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."}],"proteins":[{"created_at":"2011-05-26T19:31:39.000Z","updated_at":"2011-05-26T19:31:39.000Z","name":"Uncharacterized protein YKL215C","uniprot_id":"P28273","uniprot_name":"YKV5_YEAST","enzyme":true,"transporter":false,"gene_name":null,"num_residues":1286,"molecular_weight":"140426.0","theoretical_pi":"6.75","general_function":"Involved in hydrolase activity","specific_function":null,"reactions":[{"id":2576,"direction":"\u003e","locations":"Cytoplasmic","altext":"ATP + 5-oxo-L-proline + 2 H(2)O = ADP + phosphate + L-glutamate.","export":false,"pw_reaction_id":null,"source":null}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Cytoplasmic","genbank_gene_id":"X75951","genbank_protein_id":"473135","gene_card_id":null,"chromosome_location":null,"locus":"YKL215C","synonyms":[],"enzyme_classes":["3.5.2.9"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" hydrolase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"Hydant_A_N","identifier":"PF05378"},{"name":"Hydantoinase_A","identifier":"PF01968"},{"name":"Hydantoinase_B","identifier":"PF02538"}],"pathways":[],"gene_sequence":"ATGCAGAAAGGAAACATAAGAATTGCCATCGATAAGGGTGGAACTTTCACTGATTGTGTGGGGAATATTGGTACAGGTAAACAAGAACATGATACTGTCATCAAGCTCTTGTCGGTGGATCCCAAAAACTATCCAGATGCTCCCCTTGAAGGCATAAGACGTCTCTTGGAGGTGCTTGAACACAAGACAATTCCTCGCGGTATTCCTCTAGACATCTCTAATGTGAGAAGTTTAAGAATGGGGACAACCCTAGCTACAAACTGCGCTCTAGAAAGAAATGGTGAACGTTGTGCCTTCATTACTACGAAAGGCTTTAAGGATTCATTGCTGATTGGAGACCAAACCAGGCCAGATATCTTCAACTTAAATATAAAAAAGGTAGTGCCATTATATGACACTGTAGTTGAAATAGATGAGAGAGTTACTTTAGAAGATTTCTCGGAAGACCCTTATTTTACCAAATCGTCTCCTAATGAACAAGAAGGTATCCTGGAAGGTAATAGTGGCGAAATGGTAAGGGTCATAAAGAAGCCAGATGAATCAAGCGTAAGATCTATTCTGAAAGTGCTTTATGCTAGCGGAATCAAGTCTATTGCGATAGCATTTTTACACTCATACACTTTTCCAGACCATGAGCGAATTGTTGGTAATATTGCCAGGGAGATTGGGTTTTCTCATGTTTCATTATCATCTGAAGTCTCTCCAATGATAAAATTTTTACCGAGGGCTCACAGTTCTGTCGCAGATGCCTACCTTACTCCGGTAATTAAAAAGTACTTGAATAGCATTTCTGCAGGTTTGAGCCACGCAGAAGATACCCACATTCAATTCATGCAGTCTGATGGTGGTTTAGTGGATGGGGGAAAATTTTCCGGTTTGAAATCTATTTTATCTGGTCCTGCAGGTGGCGTAATAGGTTATTCTAGTACATGCTATGATAAAAATAATAACATACCCTTAATAGGCTTTGACATGGGAGGAACATCTACTGATGTCAGTAGGTACGGCGATGGGAGGTTAGAACATGTTTTTGAAACTGTTACCGCAGGGATCATCATACAATCTCCTCAACTTGACATCCATACTGTTGCTGCTGGAGGAAGTTCTATTTTGTCATGGAAAAACGGGTTATTCAGAGTAGGCCCTGATTCAGCAGCTGCTGATCCAGGCCCTGCAGCCTACAGAAAGGGCGGGCCTTTGACCATTACAGACGCCAACCTCTTTTTAGGACGTTTGGTTCCTGAGTTCTTCCCCAAAATTTTTGGGCCCAATGAGGATGAATCACTTGACTTAGAAACCACTACTTTGAAATTCAGAGAATTAACAGATGTCATCAATAAGGATCTGAATTCAAATCTAACCATGGAAGAGGTTGCCTATGGATTTATCAAAGTAGCTAACGAATGCATGGCAAGACCTGTGAGGGCCATTACAGAAGCAAAAGGACATGTAGTATCTCAGCATCGGTTAGTTTCCTTTGGCGGGGCTGGCGGGCAACACGCCATAGCGGTTGCAGATTCATTGGGCATTGACACTGTTTTAATTCATAGATATTCTTCTATCTTGTCCGCTTATGGCATTTTCTTAGCAGATGTTATTGAAGAAAACCAAGAGCCTTGCTCTTTTATCTTGGGTGAGCCAGAGACCATCTTGAAAGTGAAAAAAAGATTCTTAGAACTTTCTAAAAATTCAATCAAAAACCTTTTATCTCAGTCGTTTTCTCGGGAGGACATAGTCTTGGAAAGATATTTAAATCTCAGATATGAAGGTACTGAAACCAGTTTGATGATATTACAAAAATATGATGACCAATGGAATTTTAGGGAATGGTTCTCTGAAGCTCATAAAAAAGAGTTCGGATTCTCATTCGATGACAAACGAATTATAATTGATGATATAAGGATAAGAGCAATTGGGAAATCAGGCGTTAGAAAAGAAAAAACGGTTGATGAGCAATTGATTGAAATTTCCCATTTCAAGAAAGCCGACGTGTCAAAGGATGCTAGTTTTACCCAGAAAGCATATTTTGACAACAAATGGGTCGACACTGCGGTCTTCAAAATTGATGATCTTCCTGCCGGAACAATTATCGAGGGCCCAGCCATATTGGCTGACGGTACCCAAACAAATATTATTTTACCAAACAGCCAAGCAACAATTTTAAACTCTCATATATTTATCAAGATCAACCAAAAGGCTGCGAAGACATTATCTAAAAGCGGATATGAACTTGATATAGATCCAATCTTATTGTCTATTTTCAGTCATAGGTTTATGGATATCGCCCTCCAGATGGGTACTCAATTGAGGAAAACTTCTGTTTCAACTAACGTCAAAGAGAGATTAGATTTTTCATGTGCACTATTCGACTCTAAAGGAAACTTAGTCGCTAACGCTCCTCATGTACCTGTTCACTTAGGATCAATGTCAACCTGCATATCAGCACAGGCGAAGTTATGGGAAGGCAAATTAAAGCCTGGTGATGTTTTAATCACAAACCATCCGGATATTGGTGGTACTCATTTACCAGACATAACAGTAATAACTCCTTCTTTCTCTTCAACTGGCGAATTGATATTTTATGTGGCTTCAAGAGCCCATCATGCAGATATTGGAGGTATTCTACCCGGTTCAGTGCCTCCAAATTCCAAAGAATTGTACGAAGAAGGAACCGCAATTTATTCCGAATTGGTTGTCAAAGAGGGAATTTTCCAGGAAGAATTAATTTACAAGCTTTTCGTAGAAGATCCAGGCAAATACCCAGGCTGCTCAGGTTCAAGAAGATTTAGTGATAACATAAGCGATTTAAAAGCGCAAGTCGCAGCTAACACAAAAGGGATACAGTTAATTGGGTCATTAACTAAGGAATATGATCTGGCTACAATATTGAAATACATGGCTGCAATTCAGACAAATGCATCTGAATCCATAAAAAAAATGCTTGCAAAAATGGTTGAACATTTTGGCACAACGAAGTTTTCTGGCGAAGATCGCTTAGATGATGGAAGCTTAATTAAACTACAAGTTATCATAAGACCTGAAAAAGAGGAGTATATTTTTAATTTCGATGGCACTTCTCCCCAAGTTTATGGTAATTTAAATGCACCAGAGGCTATTACTAATTCTGCGATTCTTTATTGTCTACGGTGTCTAGTAGGCGAAGATATTCCTTTAAATCAAGGTTGTTTAAAACCCTTAACAATAAAAATTCCTGCTGGTTCCCTCTTGAGCCCCCGATCCGGTGCTGCTGTTGTCGGAGGCAATGTATTAACTTCCCAAAGAGTGACAGATGTAATCTTAAAAACATTTAACGTCATGGCAGATTCTCAAGGTGACTGTAACAACTTTACATTTGGAACTGGAGGAAATTCTGGTAACAAAACCGATAAGCAGATCAAAGGCTTTGGATATTATGAAACCATATGTGGCGGCTCGGGGGCTGGTGCAGATTCATGGAGAGGAAGTGGTTGGAATGGCTCAGACGCTGTACACACGAATATGACCAATACAAGAATGACAGATACTGAGGTATTTGAAAGGAGATACCCCGTTCTGTTGAAAGAGTTCTCGATCAGAAGAGGTTCAGGAGGCAAAGGTAAATATACTGGCGGAAATGGCGTAGTAAGGGATGTTCAATTTCGGAAGGCTGTAACAGCATCTATATTATCAGAACGTCGTGTCATTGGCCCTCATGGTATAAAGGGAGGACAAGACGGTAGTAGAGGTGAGAATTTATGGGTAAGACATAGCACAGGCGCATTAATCAATGTCGGCGGTAAAAATACGATTTACGCTCAACCCGGTGATCGATTCATCATTAAAACCCCTGGTGGTGGGGGATTTGGACAATACAAGGATTAA","protein_sequence":"MQKGNIRIAIDKGGTFTDCVGNIGTGKQEHDTVIKLLSVDPKNYPDAPLEGIRRLLEVLEHKTIPRGIPLDISNVRSLRMGTTLATNCALERNGERCAFITTKGFKDSLLIGDQTRPDIFNLNIKKVVPLYDTVVEIDERVTLEDFSEDPYFTKSSPNEQEGILEGNSGEMVRVIKKPDESSVRSILKVLYASGIKSIAIAFLHSYTFPDHERIVGNIAREIGFSHVSLSSEVSPMIKFLPRAHSSVADAYLTPVIKKYLNSISAGLSHAEDTHIQFMQSDGGLVDGGKFSGLKSILSGPAGGVIGYSSTCYDKNNNIPLIGFDMGGTSTDVSRYGDGRLEHVFETVTAGIIIQSPQLDIHTVAAGGSSILSWKNGLFRVGPDSAAADPGPAAYRKGGPLTITDANLFLGRLVPEFFPKIFGPNEDESLDLETTTLKFRELTDVINKDLNSNLTMEEVAYGFIKVANECMARPVRAITEAKGHVVSQHRLVSFGGAGGQHAIAVADSLGIDTVLIHRYSSILSAYGIFLADVIEENQEPCSFILGEPETILKVKKRFLELSKNSIKNLLSQSFSREDIVLERYLNLRYEGTETSLMILQKYDDQWNFREWFSEAHKKEFGFSFDDKRIIIDDIRIRAIGKSGVRKEKTVDEQLIEISHFKKADVSKDASFTQKAYFDNKWVDTAVFKIDDLPAGTIIEGPAILADGTQTNIILPNSQATILNSHIFIKINQKAAKTLSKSGYELDIDPILLSIFSHRFMDIALQMGTQLRKTSVSTNVKERLDFSCALFDSKGNLVANAPHVPVHLGSMSTCISAQAKLWEGKLKPGDVLITNHPDIGGTHLPDITVITPSFSSTGELIFYVASRAHHADIGGILPGSVPPNSKELYEEGTAIYSELVVKEGIFQEELIYKLFVEDPGKYPGCSGSRRFSDNISDLKAQVAANTKGIQLIGSLTKEYDLATILKYMAAIQTNASESIKKMLAKMVEHFGTTKFSGEDRLDDGSLIKLQVIIRPEKEEYIFNFDGTSPQVYGNLNAPEAITNSAILYCLRCLVGEDIPLNQGCLKPLTIKIPAGSLLSPRSGAAVVGGNVLTSQRVTDVILKTFNVMADSQGDCNNFTFGTGGNSGNKTDKQIKGFGYYETICGGSGAGADSWRGSGWNGSDAVHTNMTNTRMTDTEVFERRYPVLLKEFSIRRGSGGKGKYTGGNGVVRDVQFRKAVTASILSERRVIGPHGIKGGQDGSRGENLWVRHSTGALINVGGKNTIYAQPGDRFIIKTPGGGGFGQYKD"}]}