{"ymdb_id":"YMDB00872","created_at":"2011-05-29T19:00:14.000Z","updated_at":"2016-09-08T18:36:00.000Z","name":"(S)-3-hydroxy-3-methylglutaryl-CoA","cas":"1553-55-5","state":"Solid","melting_point":null,"description":"HMG-CoA (or 3-hydroxy-3-methylglutaryl-coenzyme A) is an intermediate in the Mevalonate pathway. It is formed from acetyl CoA and acetoacetyl CoA by HMG-CoA synthase.","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":null,"synthesis_reference":null,"chebi_id":"15467","hmdb_id":"HMDB01375","kegg_id":"C00356","pubchem_id":"50986137","cs_id":null,"foodb_id":null,"wikipedia_link":"3-hydroxy-3-methylglutaryl-CoA","biocyc_id":"3-HYDROXY-3-METHYL-GLUTARYL-COA","iupac":"(3S)-5-[(2-{3-[(2R)-3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido]propanamido}ethyl)sulfanyl]-3-hydroxy-3-methyl-5-oxopentanoic acid","traditional_iupac":"HMG-CoA","logp":"-6.406678756765139","pka":"1.8977913368307053","alogps_solubility":"4.10e+00 g/l","alogps_logp":"-0.53","alogps_logs":"-2.35","acceptor_count":"20","donor_count":"11","rotatable_bond_count":"24","polar_surface_area":"421.1599999999999","refractivity":"193.70200000000006","polarizability":"82.3702140669648","formal_charge":"0","physiological_charge":"-5","pka_strongest_basic":"3.810786962925538","pka_strongest_acidic":"0.8207666712061181","bioavailability":"0","number_of_rings":"3","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"1","synonyms":["(S)-3-Hydroxy-3-methylglutaryl-CoA","(S)-3-hydroxy-3-methylglutaryl-Coenzyme A","3-hydroxy-3-methyl-Glutaryl-CoA","3-hydroxy-3-methyl-Glutaryl-Coenzyme A","3-hydroxy-3-methylglutaryl-coa","3-Hydroxy-3-methylglutaryl-coenzyme A","hmg-coa","HMG-Coenzyme A","hydroxymethylglutaroyl coenzyme a","Hydroxymethylglutaryl-CoA","Hydroxymethylglutaryl-Coenzyme A","S-(Hydrogen 3-hydroxy-3-methylglutaryl)coenzyme A","S-(Hydrogen 3-hydroxy-3-methylpentanedioate","S-(Hydrogen 3-hydroxy-3-methylpentanedioate) coenzyme A","S-(Hydrogen 3-hydroxy-3-methylpentanedioic acid"],"pathways":[{"name":"Terpenoid backbone biosynthesis","kegg_map_id":"00900"},{"name":"Synthesis and degradation of ketone bodies","kegg_map_id":"00072"},{"name":"Butanoate metabolism","kegg_map_id":"00650"},{"name":"Valine, leucine and isoleucine degradation","kegg_map_id":"00280"},{"name":"Steroid biosynthesis","kegg_map_id":"00100"},{"name":"Ketone Body Metabolism","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(14:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(10:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(12:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(16:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(18:0)","kegg_map_id":null}],"growth_conditions":[],"references":[{"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":4561618,"citation":"Middleton, B. (1972). \"The kinetic mechanism of 3-hydroxy-3-methylglutaryl-coenzyme A synthase from baker's yeast.\" Biochem J 126:35-47."},{"pubmed_id":456161,"citation":"Serafin, J., Kreczko, R. (1979). \"[Use of transcondylar and metaphyseal osteotomies of the tibia in the treatment of degenerative changes of the knee joint].\" Chir Narzadow Ruchu Ortop Pol 44:141-148."}],"proteins":[{"created_at":"2011-05-24T21:42:53.000Z","updated_at":"2011-05-27T15:00:58.000Z","name":"Hydroxymethylglutaryl-CoA synthase","uniprot_id":"P54839","uniprot_name":"HMCS_YEAST","enzyme":true,"transporter":false,"gene_name":"ERG13","num_residues":491,"molecular_weight":"55013.10156","theoretical_pi":"8.32","general_function":"Involved in hydroxymethylglutaryl-CoA synthase activity","specific_function":"This enzyme condenses acetyl-CoA with acetoacetyl-CoA to form HMG-CoA, which is the substrate for HMG-CoA reductase","reactions":[{"id":1649,"direction":"\u003c\u003e","locations":"mitochondrion;cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2393,"direction":"\u003e","locations":null,"altext":"Acetyl-CoA + H(2)O + acetoacetyl-CoA = (S)-3-hydroxy-3-methylglutaryl-CoA + CoA.","export":false,"pw_reaction_id":null,"source":null},{"id":14368,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006886","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":null,"genbank_gene_id":"X96617","genbank_protein_id":"1304355","gene_card_id":"ERG13","chromosome_location":"chromosome 13","locus":"YML126C","synonyms":["HMG-CoA synthase","3-hydroxy-3-methylglutaryl coenzyme A synthase"],"enzyme_classes":["2.3.3.10"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" hydroxymethylglutaryl-CoA synthase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring acyl groups"},{"category":"Function","description":" transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer"},{"category":"Process","description":" isoprenoid metabolic process"},{"category":"Process","description":" isoprenoid biosynthetic process"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" primary metabolic process"},{"category":"Process","description":" lipid metabolic process"},{"category":"Process","description":" cellular lipid metabolic process"}],"pfams":[{"name":"HMG_CoA_synt_C","identifier":"PF08540"},{"name":"HMG_CoA_synt_N","identifier":"PF01154"}],"pathways":[{"name":"Synthesis and degradation of ketone bodies","kegg_map_id":"00072"},{"name":"Valine, leucine and isoleucine degradation","kegg_map_id":"00280"},{"name":"Butanoate metabolism","kegg_map_id":"00650"},{"name":"Terpenoid backbone biosynthesis","kegg_map_id":"00900"},{"name":"Cholesterol biosynthesis and metabolism CE(10:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(12:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(14:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(16:0)","kegg_map_id":null},{"name":"Cholesterol biosynthesis and metabolism CE(18:0)","kegg_map_id":null},{"name":"Ketone Body Metabolism","kegg_map_id":null},{"name":"Steroid biosynthesis","kegg_map_id":"00100"}],"gene_sequence":"ATGAAACTCTCAACTAAACTTTGTTGGTGTGGTATTAAAGGAAGACTTAGGCCGCAAAAGCAACAACAATTACACAATACAAACTTGCAAATGACTGAACTAAAAAAACAAAAGACCGCTGAACAAAAAACCAGACCTCAAAATGTCGGTATTAAAGGTATCCAAATTTACATCCCAACTCAATGTGTCAACCAATCTGAGCTAGAGAAATTTGATGGCGTTTCTCAAGGTAAATACACAATTGGTCTGGGCCAAACCAACATGTCTTTTGTCAATGACAGAGAAGATATCTACTCGATGTCCCTAACTGTTTTGTCTAAGTTGATCAAGAGTTACAACATCGACACCAACAAAATTGGTAGATTAGAAGTCGGTACTGAAACTCTGATTGACAAGTCCAAGTCTGTCAAGTCTGTCTTGATGCAATTGTTTGGTGAAAACACTGACGTCGAAGGTATTGACACGCTTAATGCCTGTTACGGTGGTACCAACGCGTTGTTCAACTCTTTGAACTGGATTGAATCTAACGCATGGGATGGTAGAGACGCCATTGTAGTTTGCGGTGATATTGCCATCTACGATAAGGGTGCCGCAAGACCAACCGGTGGTGCCGGTACTGTTGCTATGTGGATCGGTCCTGATGCTCCAATTGTATTTGACTCTGTAAGAGCTTCTTACATGGAACACGCCTACGATTTTTACAAGCCAGATTTCACCAGCGAATATCCTTACGTCGATGGTCATTTTTCATTAACTTGTTACGTCAAGGCTCTTGATCAAGTTTACAAGAGTTATTCCAAGAAGGCTATTTCTAAAGGGTTGGTTAGCGATCCCGCTGGTTCGGATGCTTTGAACGTTTTGAAATATTTCGACTACAACGTTTTCCATGTTCCAACCTGTAAATTGGTCACAAAATCATACGGTAGATTACTATATAACGATTTCAGAGCCAATCCTCAATTGTTCCCAGAAGTTGACGCCGAATTAGCTACTCGCGATTATGACGAATCTTTAACCGATAAGAACATTGAAAAAACTTTTGTTAATGTTGCTAAGCCATTCCACAAAGAGAGAGTTGCCCAATCTTTGATTGTTCCAACAAACACAGGTAACATGTACACCGCATCTGTTTATGCCGCCTTTGCATCTCTATTAAACTATGTTGGATCTGACGACTTACAAGGCAAGCGTGTTGGTTTATTTTCTTACGGTTCCGGTTTAGCTGCATCTCTATATTCTTGCAAAATTGTTGGTGACGTCCAACATATTATCAAGGAATTAGATATTACTAACAAATTAGCCAAGAGAATCACCGAAACTCCAAAGGATTACGAAGCTGCCATCGAATTGAGAGAAAATGCCCATTTGAAGAAGAACTTCAAACCTCAAGGTTCCATTGAGCATTTGCAAAGTGGTGTTTACTACTTGACCAACATCGATGACAAATTTAGAAGATCTTACGATGTTAAAAAATAA","protein_sequence":"MKLSTKLCWCGIKGRLRPQKQQQLHNTNLQMTELKKQKTAEQKTRPQNVGIKGIQIYIPTQCVNQSELEKFDGVSQGKYTIGLGQTNMSFVNDREDIYSMSLTVLSKLIKSYNIDTNKIGRLEVGTETLIDKSKSVKSVLMQLFGENTDVEGIDTLNACYGGTNALFNSLNWIESNAWDGRDAIVVCGDIAIYDKGAARPTGGAGTVAMWIGPDAPIVFDSVRASYMEHAYDFYKPDFTSEYPYVDGHFSLTCYVKALDQVYKSYSKKAISKGLVSDPAGSDALNVLKYFDYNVFHVPTCKLVTKSYGRLLYNDFRANPQLFPEVDAELATRDYDESLTDKNIEKTFVNVAKPFHKERVAQSLIVPTNTGNMYTASVYAAFASLLNYVGSDDLQGKRVGLFSYGSGLAASLYSCKIVGDVQHIIKELDITNKLAKRITETPKDYEAAIELRENAHLKKNFKPQGSIEHLQSGVYYLTNIDDKFRRSYDVKK"}]}