{"ymdb_id":"YMDB00334","created_at":"2011-05-29T18:07:13.000Z","updated_at":"2016-09-08T18:35:21.000Z","name":"Lipoic acid","cas":"1077-28-7","state":"Solid","melting_point":"60.5 oC","description":"(R)-Lipoate is a sulfur-containing cofactor found in many prokaryotic and eukaryotic organisms. It is utilized by several enzymes involved in oxidative metabolism, including pyruvate dehydrogenase multienzyme complex, 2-oxoglutarate dehydrogenase complex, branched-chain alpha-keto acid dehydrogenase complex, and the glycine cleavage system. [Biocyc PWY0-522]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":"","location":null,"synthesis_reference":null,"chebi_id":"30314","hmdb_id":"HMDB01451","kegg_id":"C00725","pubchem_id":"864","cs_id":"5886","foodb_id":null,"wikipedia_link":"Lipoic_acid","biocyc_id":"LIPOIC-ACID","iupac":"5-[(3R)-1,2-dithiolan-3-yl]pentanoic acid","traditional_iupac":"lipoic acid","logp":"2.1137794076666667","pka":null,"alogps_solubility":"2.24e-01 g/l","alogps_logp":"2.75","alogps_logs":"-2.96","acceptor_count":"2","donor_count":"1","rotatable_bond_count":"5","polar_surface_area":"37.3","refractivity":"54.3714","polarizability":"21.744975428939433","formal_charge":"0","physiological_charge":"-1","pka_strongest_basic":null,"pka_strongest_acidic":"4.523468122735193","bioavailability":"1","number_of_rings":"1","rule_of_five":"1","ghose_filter":"1","veber_rule":"1","mddr_like_rule":"0","synonyms":["(+-)-1,2-Dithiolane-3-pentanoate","(+-)-1,2-Dithiolane-3-pentanoic acid","(+-)-1,2-Dithiolane-3-valerate","(+-)-1,2-Dithiolane-3-valeric acid","(+)-alpha-Lipoate","(+)-alpha-Lipoic acid","(R)-1,2-Dithiolane-3-pentanoate","(R)-1,2-Dithiolane-3-pentanoic acid","(RS)-alpha-Lipoate","(RS)-alpha-Lipoic acid","(RS)-Lipoate","(RS)-Lipoic acid","1,2-Dithiolane-3-pentanoate","1,2-Dithiolane-3-pentanoic acid","1,2-Dithiolane-3-valerate","1,2-Dithiolane-3-valeric acid","1,2-Dithiolane-3R-pentanoate","1,2-Dithiolane-3R-pentanoic acid","5-(1,2-Dithiolan-3-yl)pentanoate","5-(1,2-Dithiolan-3-yl)pentanoic acid","5-(1,2-Dithiolan-3-yl)valerate","5-(1,2-Dithiolan-3-yl)valeric acid","5-(Dithiolan-3-yl)valerate","5-(Dithiolan-3-yl)valeric acid","5-[3-(1,2-dithiolanyl)]pentanoate","5-[3-(1,2-dithiolanyl)]pentanoic acid","6-Thioctate","6-Thioctic acid","6-Thiotate","6-Thiotic acid","6,8-Dithiooctanoate","6,8-Dithiooctanoic acid","6,8-Thioctate","6,8-Thioctic acid","6,8-Thiotate","6,8-Thiotic acid","acetate replacing factor","Acetate-replacing factor","alpha Lipoate","alpha Lipoic acid","alpha-Lipoate","alpha-Lipoic acid","alpha-Liponate","alpha-Liponic acid","alpha-Liponsaeure","Biletan","delta-[3-(1,2-dithiacyclopentyl)]pentanoate","delta-[3-(1,2-dithiacyclopentyl)]pentanoic acid","DL-1,2-Dithiolane 3-valerate","DL-1,2-Dithiolane 3-valeric acid","DL-6-Thioctate","DL-6-Thioctic acid","DL-6,8-Dithiooctanoate","DL-6,8-Dithiooctanoic acid","DL-6,8-Thioctate","DL-6,8-Thioctic acid","DL-alpha-Lipoate","DL-alpha-Lipoic acid","dl-Lipoate","dl-Lipoic acid","dl-Thioctate","dl-Thioctic acid","DL-Thioctic acid \u003e 98%","Heparlipon","Lip","Lipoate","Lipoic acid","liponate","liponic acid","Liposan","Lipothion","Protogen A","Pyruvate oxidation factor","R-Lipoate","R-Lipoic acid","Rac-lipoate","Rac-lipoic acid","Thioctacid","Thioctan","Thioctate","Thioctic acid","Thioctic acid d-form","Thioctic acid dl-form","Thioctidase","Thioctsan","Thioktsaeure","Thiooctanoate","Thiooctanoic acid","Tioctacid","Tioctan","Tioctidasi","Tioctidasi acetate replacing factor"],"pathways":[{"name":"Lipoic acid metabolism","kegg_map_id":"00785"}],"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":"2011-05-29T04:40:13.000Z","updated_at":"2011-05-29T05:06:53.000Z","name":"Putative lipoate-protein ligase A","uniprot_id":"P47051","uniprot_name":"LPLA_YEAST","enzyme":true,"transporter":false,"gene_name":"AIM22","num_residues":409,"molecular_weight":"47003.0","theoretical_pi":"7.52","general_function":"Involved in catalytic activity","specific_function":"Catalyzes both the ATP-dependent activation of exogenously supplied lipoate to lipoyl-AMP and the transfer of the activated lipoyl onto the lipoyl domains of lipoate-dependent enzymes","reactions":[{"id":2846,"direction":"\u003e","locations":null,"altext":"ATP + lipoate = diphosphate + lipoyl-AMP.","export":false,"pw_reaction_id":null,"source":null},{"id":2847,"direction":"\u003e","locations":null,"altext":"Lipoyl-AMP + protein = protein N(6)-(lipoyl)lysine + AMP.","export":false,"pw_reaction_id":null,"source":null},{"id":14862,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R007050","source":"Smpdb"},{"id":14863,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R007051","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":null,"genbank_protein_id":null,"gene_card_id":"AIM22","chromosome_location":"chromosome 10","locus":"YJL046W","synonyms":["Altered inheritance rate of mitochondria protein 22"],"enzyme_classes":["2.7.7.63"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" macromolecule metabolic process"},{"category":"Process","description":" macromolecule modification"},{"category":"Process","description":" protein modification process"},{"category":"Process","description":" post-translational protein modification"},{"category":"Process","description":" protein-cofactor linkage"},{"category":"Process","description":" protein lipoylation"}],"pfams":[{"name":"BPL_LipA_LipB","identifier":"PF03099"}],"pathways":[{"name":"Lipoic acid metabolism","kegg_map_id":"00785"}],"gene_sequence":"ATGTCTATGATGCTAAGTAATTGGGCACTCTCCCCTCGATATGTGGGACAGCGAAACCTCATACATTGCACCACTTTATTTCACACACTTACACGATGGGCAAAAGACGCAGACGATAAATATCATGATATAAACTCAATGTATGAAAACATGTTTACACCTTCAAATGATAACGTTTCAATTTTGCAGGATGAAGGTAAATCTGATTATGATACGACGAAGGCCAGCTCTATGGAAGAAGATATCAGTGCTTTTAATAAAGACTTGTACAATTTCTATAATATTGGATATGCCAAACAGATCATGTCTGCTTCACAATTGGAAAATATAGTAAAGGCAAAGGGCAGATTTGTTATACAAAGTTTATCCACCAGTCCTTATTATAATTTGGCCCTTGAAAACTATGTTTTCAAGAATACACCAAGAGCCAAAAGAGGTCCCGATAATTGCAGACTGTTATTTTACATCAATGATAGGTGCGCCGTTATAGGCAAAAACCAAAATCTGTGGCAGGAAGTAGATCTTGCTAAGCTGAAGAGTAAGAATTTCGAACTACTTAGAAGATTTTCTGGAGGTGGCACTGTACTGCATGATTTGGGCAATGTTAATTATTCATATTTAACATCAAGGGAGAAATTCGAAACAAAGTTTTTCAACAAAATGATAATTAAGTGGTTAAATTCATTGAATCCCGAACTAAGACTAGATTTGAATGAGAGAGGAGATATTATTCAGGACGGGTTTAAAATTAGTGGCAGTGCTTATAAAATTGCCGGTGGCAAAGCATACCATCATGCAACGATGTTGCTTAATGCGGATTTAGAACAGTTTAGCGGCTTATTAGAACCCTCACTACCGAACAATATGGAATGGGAGTCAAGTGGAGTTCATAGTGTAAAATCAAAAATCAAAAATGTTGGTATAATTACTCCTAATCAGTTCATTGCAGTGGTATCCGAGCGTTTTCAGAAAACATTCAAAGTTGACGGCGAAATACCTATATATTACTGTGACGAGTTTAAATCTATAAACGATGAGATTAAAGATGCTATGAACACCTTACAGAGCGAACAATGGAAATATTTCTCGGGGCCTAAATTTTCAGTGAAGATTAAAGATAAAGGCTTAACAATTAAAGTCGAAAAGGGCATGATTTATGATTGTGATAGAAATGATTTAATCGGCTTGGAATTCAAAGGATTTTTGGAGAATATTGACAGTTACACATAA","protein_sequence":"MSMMLSNWALSPRYVGQRNLIHCTTLFHTLTRWAKDADDKYHDINSMYENMFTPSNDNVSILQDEGKSDYDTTKASSMEEDISAFNKDLYNFYNIGYAKQIMSASQLENIVKAKGRFVIQSLSTSPYYNLALENYVFKNTPRAKRGPDNCRLLFYINDRCAVIGKNQNLWQEVDLAKLKSKNFELLRRFSGGGTVLHDLGNVNYSYLTSREKFETKFFNKMIIKWLNSLNPELRLDLNERGDIIQDGFKISGSAYKIAGGKAYHHATMLLNADLEQFSGLLEPSLPNNMEWESSGVHSVKSKIKNVGIITPNQFIAVVSERFQKTFKVDGEIPIYYCDEFKSINDEIKDAMNTLQSEQWKYFSGPKFSVKIKDKGLTIKVEKGMIYDCDRNDLIGLEFKGFLENIDSYT"}]}