{"ymdb_id":"YMDB00608","created_at":"2011-05-29T18:35:35.000Z","updated_at":"2016-09-08T18:35:41.000Z","name":"zymosterol intermediate 2","cas":"128-33-6","state":"Solid","melting_point":"110 oC","description":"Zymosterol is an intermediate in the biosynthesis of both ergosterol, a major constituent of the fungal plasma membrane, and cholesterol, the homologous component in mammalian membranes. Cholesterol and ergosterol share most of their biosythetic pathway, with differences only in the part of the pathway that is downstream of zymosterol. [Biocyc PWY-6074 and PWY-6075]","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":"cytoplasm","synthesis_reference":"Dolle, Roland E.; Schmidt, Stanley J.; Kruse, Lawrence I. Synthesis of zymosterol: salient intermediate of fungal and mammalian sterol biosynthesis. Journal of the Chemical Society, Chemical Communications (1988), (1), 19-21.","chebi_id":"52386","hmdb_id":"HMDB06271","kegg_id":"C05437","pubchem_id":"92746","cs_id":"24850070","foodb_id":null,"wikipedia_link":"Zymosterol","biocyc_id":"ZYMOSTEROL","iupac":"(2S,7S,11R,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-1(10)-en-5-one","traditional_iupac":"5α-cholesta-8,24-dien-3-one","logp":"6.871152526333334","pka":null,"alogps_solubility":"7.11e-04 g/l","alogps_logp":"6.92","alogps_logs":"-5.73","acceptor_count":"1","donor_count":"0","rotatable_bond_count":"4","polar_surface_area":"17.07","refractivity":"120.17179999999998","polarizability":"48.850958266883396","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"-7.353211484801864","pka_strongest_acidic":"19.962530739976856","bioavailability":"1","number_of_rings":"4","rule_of_five":"0","ghose_filter":"0","veber_rule":"1","mddr_like_rule":"0","synonyms":["(3b,5a)- Cholesta-8,24-dien-3-ol","5-alpha-Cholesta-8,24-dien-3-beta-ol","5alpha-Cholesta-8,24-dien-3beta-ol","Cholest-8,24-dien-3b-ol","Cholest-8,24-dien-3beta-ol","Cholesta-8,24-dien-3-ol","delta8,24-Cholestadien-3beta-ol","Zymosterol"],"pathways":[{"name":"Steroid biosynthesis","kegg_map_id":"00100"},{"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}],"growth_conditions":[],"references":[{"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":7896706,"citation":"Loubbardi, A., Marcireau, C., Karst, F., Guilloton, M. (1995). \"Sterol uptake induced by an impairment of pyridoxal phosphate synthesis in Saccharomyces cerevisiae: cloning and sequencing of the PDX3 gene encoding pyridoxine (pyridoxamine) phosphate oxidase.\" J Bacteriol 177:1817-1823."}],"proteins":[{"created_at":"2011-05-24T20:59:15.000Z","updated_at":"2011-07-22T17:54:20.000Z","name":"3-keto-steroid reductase","uniprot_id":"Q12452","uniprot_name":"ERG27_YEAST","enzyme":true,"transporter":false,"gene_name":"ERG27","num_residues":347,"molecular_weight":"39724.39844","theoretical_pi":"8.64","general_function":"Involved in binding","specific_function":"Responsible for the reduction of the keto group on the C-3 of sterols. Also facilitates the association of ERG7 with lipid particles preventing its digestion in the endoplasmic reticulum and the lipid particles","reactions":[{"id":1354,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1355,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2354,"direction":"\u003e","locations":"Endoplasmic reticulum membrane; Peripheral membrane protein. Lipid droplet","altext":"4-alpha-methyl-5-alpha-cholest-7-en-3-beta-ol + NADP(+) = 4-alpha-methyl-5-alpha-cholest-7-en-3-one + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":14391,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006902","source":"Smpdb"},{"id":14407,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006918","source":"Smpdb"},{"id":14408,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006923","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Endoplasmic reticulum membrane; Peripheral membrane protein. Lipid droplet","genbank_gene_id":"U53876","genbank_protein_id":"1256850","gene_card_id":"ERG27","chromosome_location":"chromosome 12","locus":"YLR100W","synonyms":[],"enzyme_classes":["1.1.1.270"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Process","description":" metabolic process"}],"pfams":[],"pathways":[{"name":"Steroid biosynthesis","kegg_map_id":"00100"},{"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}],"gene_sequence":"ATGAACAGGAAAGTAGCTATCGTAACGGGTACTAATAGTAATCTTGGTCTGAACATTGTGTTCCGTCTGATTGAAACTGAGGACACCAATGTCAGATTGACCATTGTGGTGACTTCTAGAACGCTTCCTCGAGTGCAGGAGGTGATTAACCAGATTAAAGATTTTTACAACAAATCAGGCCGTGTAGAGGATTTGGAAATAGACTTTGATTATCTGTTGGTGGACTTCACCAACATGGTGAGTGTCTTGAACGCATATTACGACATCAACAAAAAGTACAGGGCGATAAACTACCTTTTCGTGAATGCTGCGCAAGGTATCTTTGACGGTATAGATTGGATCGGAGCGGTCAAGGAGGTTTTCACCAATCCATTGGAGGCAGTGACAAATCCGACATACAAGATACAACTGGTGGGCGTCAAGTCTAAAGATGACATGGGGCTTATTTTCCAGGCCAATGTGTTTGGTCCGTACTACTTTATCAGTAAAATTCTGCCTCAATTGACCAGGGGAAAGGCTTATATTGTTTGGATTTCGAGTATTATGTCCGATCCTAAGTATCTTTCGTTGAACGATATTGAACTACTAAAGACAAATGCCTCTTATGAGGGCTCCAAGCGTTTAGTTGATTTACTGCATTTGGCCACCTACAAAGACTTGAAAAAGCTGGGCATAAATCAGTATGTAGTTCAACCGGGCATATTTACAAGCCATTCCTTCTCCGAATATTTGAATTTTTTCACCTATTTCGGCATGCTATGCTTGTTCTATTTGGCCAGGCTGTTGGGGTCTCCATGGCACAATATTGATGGTTATAAAGCTGCCAATGCCCCAGTATACGTAACTAGATTGGCCAATCCAAACTTTGAGAAACAAGACGTAAAATACGGTTCTGCTACCTCTAGGGATGGTATGCCATATATCAAGACGCAGGAAATAGACCCTACTGGAATGTCTGATGTCTTCGCTTATATACAGAAGAAGAAACTGGAATGGGACGAGAAACTGAAAGATCAAATTGTTGAAACTAGAACCCCCATTTAA","protein_sequence":"MNRKVAIVTGTNSNLGLNIVFRLIETEDTNVRLTIVVTSRTLPRVQEVINQIKDFYNKSGRVEDLEIDFDYLLVDFTNMVSVLNAYYDINKKYRAINYLFVNAAQGIFDGIDWIGAVKEVFTNPLEAVTNPTYKIQLVGVKSKDDMGLIFQANVFGPYYFISKILPQLTRGKAYIVWISSIMSDPKYLSLNDIELLKTNASYEGSKRLVDLLHLATYKDLKKLGINQYVVQPGIFTSHSFSEYLNFFTYFGMLCLFYLARLLGSPWHNIDGYKAANAPVYVTRLANPNFEKQDVKYGSATSRDGMPYIKTQEIDPTGMSDVFAYIQKKKLEWDEKLKDQIVETRTPI"},{"created_at":"2011-05-27T02:38:20.000Z","updated_at":"2011-07-22T17:54:20.000Z","name":"Sterol-4-alpha-carboxylate 3-dehydrogenase, decarboxylating","uniprot_id":"P53199","uniprot_name":"ERG26_YEAST","enzyme":true,"transporter":false,"gene_name":"ERG26","num_residues":349,"molecular_weight":"38706.10156","theoretical_pi":"6.67","general_function":"Involved in 3-beta-hydroxy-delta5-steroid dehydrogenase activity","specific_function":"3-beta-hydroxy-4-beta-methyl-5-alpha-cholest- 7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha- cholest-7-en-3-one + CO(2) + NAD(P)H","reactions":[{"id":1352,"direction":"\u003c\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1353,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2682,"direction":"\u003e","locations":"Endoplasmic reticulum membrane; Peripheral membrane protein","altext":"3-beta-hydroxy-4-beta-methyl-5-alpha-cholest-7-ene-4-alpha-carboxylate + NAD(P)(+) = 4-alpha-methyl-5-alpha-cholest-7-en-3-one + CO(2) + NAD(P)H.","export":false,"pw_reaction_id":null,"source":null},{"id":14405,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006917","source":"Smpdb"},{"id":14406,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006922","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"None","pdb_id":null,"cellular_location":"Endoplasmic reticulum membrane; Peripheral membrane protein","genbank_gene_id":"AY693026","genbank_protein_id":"51013503","gene_card_id":"ERG26","chromosome_location":"chromosome 7","locus":"YGL001C","synonyms":[],"enzyme_classes":["1.1.1.170"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Function","description":" steroid dehydrogenase activity"},{"category":"Function","description":" steroid dehydrogenase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor"},{"category":"Function","description":" 3-beta-hydroxy-delta5-steroid dehydrogenase activity"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" primary metabolic process"},{"category":"Process","description":" lipid metabolic process"},{"category":"Process","description":" steroid metabolic process"},{"category":"Process","description":" steroid biosynthetic process"}],"pfams":[{"name":"3Beta_HSD","identifier":"PF01073"}],"pathways":[{"name":"Steroid biosynthesis","kegg_map_id":"00100"},{"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}],"gene_sequence":"ATGTCAAAGATAGATTCAGTTTTAATTATCGGTGGTTCTGGTTTTCTTGGATTGCACTTAATTCAGCAATTTTTTGATATTAATCCTAAGCCAGACATCCACATTTTTGATGTTAGAGATCTCCCTGAAAAACTTTCAAAACAGTTTACTTTTAATGTAGACGACATAAAATTTCATAAGGGTGATTTAACATCACCTGATGATATGGAAAACGCAATTAACGAAAGTAAAGCAAATGTTGTTGTTCATTGTGCTTCTCCAATGCATGGTCAAAATCCAGATATTTATGACATAGTGAATGTTAAGGGAACCCGTAACGTGATAGATATGTGCAAGAAATGTGGCGTTAATATACTTGTATATACTTCCTCTGCTGGTGTTATTTTTAATGGGCAAGATGTGCACAATGCAGACGAAACCTGGCCAATCCCAGAAGTTCCTATGGATGCGTACAATGAGACTAAAGCTATCGCCGAAGATATGGTCTTGAAGGCGAATGATCCAAGCAGTGATTTCTATACTGTTGCTCTTCGTCCAGCTGGTATTTTTGGCCCAGGTGATAGGCAATTAGTACCTGGTCTAAGACAGGTTGCGAAATTGGGGCAGTCGAAGTTCCAAATTGGTGATAATAACAATCTATTTGATTGGACTTATGCTGGAAATGTTGCTGACGCGCATGTGTTAGCTGCACAGAAACTTCTCGATCCAAAAACAAGAACTGCTGTCTCGGGTGAAACTTTTTTCATTACCAATGATACCCCCACCTATTTTTGGGCCTTGGCCCGTACTGTGTGGAAGGCAGATGGTCATATTGATAAACATGTTATTGTTTTGAAAAGGCCAGTTGCAATTTGTGCAGGTTATCTTTCAGAATGGGTATCCAAGATGCTGGGTAAAGAGCCAGGTTTGACTCCATTCAGAGTCAAGATTGTGTGTGCATACCGTTATCACAACATTGCTAAGGCCAAAAAGTTGCTAGGCTACACACCAAGAGTTGGTATTGAAGAAGGAATTAACAAAACGTTGGCCTGGATGGACGAAGGTTTGTAA","protein_sequence":"MSKIDSVLIIGGSGFLGLHLIQQFFDINPKPDIHIFDVRDLPEKLSKQFTFNVDDIKFHKGDLTSPDDMENAINESKANVVVHCASPMHGQNPDIYDIVNVKGTRNVIDMCKKCGVNILVYTSSAGVIFNGQDVHNADETWPIPEVPMDAYNETKAIAEDMVLKANDPSSDFYTVALRPAGIFGPGDRQLVPGLRQVAKLGQSKFQIGDNNNLFDWTYAGNVADAHVLAAQKLLDPKTRTAVSGETFFITNDTPTYFWALARTVWKADGHIDKHVIVLKRPVAICAGYLSEWVSKMLGKEPGLTPFRVKIVCAYRYHNIAKAKKLLGYTPRVGIEEGINKTLAWMDEGL"}]}