{"ymdb_id":"YMDB00268","created_at":"2011-05-29T18:00:30.000Z","updated_at":"2016-09-08T18:35:16.000Z","name":"4,4-Dimethylcholesta-8,14,24-trienol","cas":"64284-64-6","state":"Solid","melting_point":"","description":"4,4-Dimethylcholesta-8,14,24-trienol is a product of the enzyme delta14-sterol reductase [EC 1.3.1.70]. It is involved in the biosynthesis of steroids and in the conversion of lanosterol to zymosterol. [KEGG]","experimental_water_solubility":"","experimental_logp_hydrophobicity":"","location":"cytoplasm","synthesis_reference":"Ruan B; Wilson W K; Schroepfer G J Jr  An alternative synthesis of 4,4-dimethyl-5 alpha-cholesta-8,14,24-trien-3 beta-ol, an intermediate in sterol biosynthesis and a reported activator of meiosis and of nuclear orphan receptor LXR alpha.    Bioorganic \u0026 ","chebi_id":"17813","hmdb_id":"HMDB01023","kegg_id":"C11455","pubchem_id":"443212","cs_id":"23232316","foodb_id":null,"wikipedia_link":null,"biocyc_id":"44-DIMETHYL-CHOLESTA-812-24-TRIENOL","iupac":"(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol","traditional_iupac":"(2S,5S,7R,14R,15R)-2,6,6,15-tetramethyl-14-[(2R)-6-methylhept-5-en-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-1(10),11-dien-5-ol","logp":"7.001045919666668","pka":null,"alogps_solubility":"1.01e-03 g/l","alogps_logp":"7.40","alogps_logs":"-5.61","acceptor_count":"1","donor_count":"1","rotatable_bond_count":"4","polar_surface_area":"20.23","refractivity":"130.9196","polarizability":"52.85549562053099","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"-0.8069737073069677","pka_strongest_acidic":"19.55378667739605","bioavailability":"1","number_of_rings":"4","rule_of_five":"0","ghose_filter":"0","veber_rule":"1","mddr_like_rule":"0","synonyms":["(3beta,5alpha)-4,4-dimethyl-Cholesta-8,14,24-trien-3-ol","(3beta,5alpha)-4,4-Dimethylcholesta-8,14,24-trien-3-ol","4,4-Dimechol-8,14,24-trienol","4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol","4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3-ol","4,4-Dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol","4,4-dimethyl-cholesta-8,14,24-trienol","4,4-Dimethylcholesta-8,14,24-trienol","4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol","FF-MAS","follicular fluid meiosis activating sterol"],"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":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":10622712,"citation":"Lamb, D. C., Kelly, D. E., Manning, N. J., Kaderbhai, M. A., Kelly, S. L. (1999). \"Biodiversity of the P450 catalytic cycle: yeast cytochrome b5/NADH cytochrome b5 reductase complex efficiently drives the entire sterol 14-demethylation (CYP51) reaction.\" FEBS Lett 462:283-288."}],"proteins":[{"created_at":"2011-05-24T20:03:33.000Z","updated_at":"2011-05-27T14:55:59.000Z","name":"Lanosterol 14-alpha demethylase","uniprot_id":"P10614","uniprot_name":"CP51_YEAST","enzyme":true,"transporter":false,"gene_name":"ERG11","num_residues":530,"molecular_weight":"60719.80078","theoretical_pi":"8.95","general_function":"Involved in iron ion binding","specific_function":"Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol","reactions":[{"id":2295,"direction":"\u003e","locations":"Membrane; Single-pass membrane protein","altext":"Obtusifoliol + 3 O(2) + 3 NADPH = 4-alpha-methyl-5-alpha-ergosta-8,14,24(28)-trien-3-beta-ol + formate + 3 NADP(+) + 4 H(2)O.","export":false,"pw_reaction_id":null,"source":null},{"id":14387,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006897","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"21-41","pdb_id":null,"cellular_location":"Membrane; Single-pass membrane protein","genbank_gene_id":"M18109","genbank_protein_id":"170946","gene_card_id":"ERG11","chromosome_location":"chromosome 8","locus":"YHR007C","synonyms":["CYPLI","Cytochrome P450 51","Cytochrome P450-14DM","Cytochrome P450-LIA1","Sterol 14-alpha demethylase"],"enzyme_classes":["1.14.13.70"],"go_classes":[{"category":"Component","description":" Not Available"},{"category":"Function","description":" binding"},{"category":"Function","description":" ion binding"},{"category":"Function","description":" cation binding"},{"category":"Function","description":" metal ion binding"},{"category":"Function","description":" transition metal ion binding"},{"category":"Function","description":" iron ion binding"},{"category":"Function","description":" oxidoreductase activity"},{"category":"Function","description":" heme binding"},{"category":"Function","description":" electron carrier activity"},{"category":"Function","description":" monooxygenase activity"},{"category":"Function","description":" catalytic activity"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"p450","identifier":"PF00067"}],"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":"ATGTCTGCTACCAAGTCAATCGTTGGAGAGGCATTGGAATACGTAAACATTGGTTTAAGTCATTTCTTGGCTTTACCATTGGCCCAAAGAATCTCTTTGATCATAATAATTCCTTTCATTTACAATATTGTATGGCAATTACTATATTCTTTGAGAAAGGACCGTCCACCTCTAGTGTTTTACTGGATTCCATGGGTCGGTAGTGCTGTTGTGTACGGTATGAAGCCATACGAGTTTTTCGAAGAATGTCAAAAGAAATACGGTGATATTTTTTCATTCGTTTTGTTAGGAAGAGTCATGACTGTGTATTTAGGACCAAAGGGTCACGAATTTGTCTTCAACGCTAAGTTGGCAGATGTTTCAGCAGAAGCTGCTTACGCTCATTTGACTACTCCAGTTTTCGGTAAAGGTGTTATTTACGATTGTCCAAATTCTAGATTGATGGAGCAAAAGAAGTTTGTTAAGGGTGCTCTAACCAAAGAAGCCTTCAAGAGCTACGTTCCATTGATTGCTGAAGAAGTGTACAAGTACTTCAGAGACTCCAAAAACTTCCGTTTGAATGAAAGAACTACTGGTACTATTGACGTGATGGTTACTCAACCTGAAATGACTATTTTCACCGCTTCAAGATCATTATTGGGTAAGGAAATGAGAGCAAAATTGGATACCGATTTTGCTTACTTGTACAGTGATTTGGATAAGGGTTTCACTCCAATCAACTTCGTCTTCCCTAACTTACCATTGGAACACTATAGAAAGAGAGATCACGCTCAAAAGGCTATCTCCGGTACTTACATGTCTTTGATTAAGGAAAGAAGAAAGAACAACGACATTCAAGACAGAGATTTGATCGATTCCTTGATGAAGAACTCTACCTACAAGGATGGTGTGAAGATGACTGATCAAGAAATCGCTAACTTGTTAATTGGTGTCTTAATGGGTGGTCAACATACTTCTGCTGCCACTTCTGCTTGGATTTTGTTGCACTTGGCTGAAAGACCAGATGTCCAACAAGAATTGTACGAAGAACAAATGCGTGTTTTGGATGGTGGTAAGAAGGAATTGACCTACGATTTATTACAAGAAATGCCATTGTTGAACCAAACTATTAAGGAAACTCTAAGAATGCACCATCCATTGCACTCTTTGTTCCGTAAGGTTATGAAAGATATGCACGTTCCAAACACTTCTTATGTCATCCCAGCAGGTTATCACGTTTTGGTTTCTCCAGGTTACACTCATTTAAGAGACGAATACTTCCCTAATGCTCACCAATTCAACATTCACCGTTGGAACAAAGATTCTGCCTCCTCTTATTCCGTCGGTGAAGAAGTCGATTACGGTTTCGGTGCCATTTCTAAGGGTGTCAGCTCTCCATACTTACCTTTCGGTGGTGGTAGACACAGATGTATCGGTGAACACTTTGCTTACTGTCAGCTAGGTGTTCTAATGTCCATTTTTATCAGAACATTAAAATGGCATTACCCAGAGGGTAAGACCGTTCCACCTCCTGACTTTACATCTATGGTTACTCTTCCAACCGGTCCAGCCAAGATCATCTGGGAAAAGAGAAATCCAGAACAAAAGATCTAA","protein_sequence":"MSATKSIVGEALEYVNIGLSHFLALPLAQRISLIIIIPFIYNIVWQLLYSLRKDRPPLVFYWIPWVGSAVVYGMKPYEFFEECQKKYGDIFSFVLLGRVMTVYLGPKGHEFVFNAKLADVSAEAAYAHLTTPVFGKGVIYDCPNSRLMEQKKFVKGALTKEAFKSYVPLIAEEVYKYFRDSKNFRLNERTTGTIDVMVTQPEMTIFTASRSLLGKEMRAKLDTDFAYLYSDLDKGFTPINFVFPNLPLEHYRKRDHAQKAISGTYMSLIKERRKNNDIQDRDLIDSLMKNSTYKDGVKMTDQEIANLLIGVLMGGQHTSAATSAWILLHLAERPDVQQELYEEQMRVLDGGKKELTYDLLQEMPLLNQTIKETLRMHHPLHSLFRKVMKDMHVPNTSYVIPAGYHVLVSPGYTHLRDEYFPNAHQFNIHRWNKDSASSYSVGEEVDYGFGAISKGVSSPYLPFGGGRHRCIGEHFAYCQLGVLMSIFIRTLKWHYPEGKTVPPPDFTSMVTLPTGPAKIIWEKRNPEQKI"},{"created_at":"2011-05-27T05:43:34.000Z","updated_at":"2011-07-22T17:54:19.000Z","name":"Delta(14)-sterol reductase","uniprot_id":"P32462","uniprot_name":"ERG24_YEAST","enzyme":true,"transporter":false,"gene_name":"ERG24","num_residues":438,"molecular_weight":"50615.0","theoretical_pi":"9.09","general_function":"Involved in delta14-sterol reductase activity","specific_function":"Reduces the C14=C15 double bond of 4,4-dimethyl- cholesta-8,14,24-trienol to produce 4,4-dimethyl-cholesta-8,24- dienol","reactions":[{"id":1349,"direction":"\u003e","locations":"cytoplasm","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2781,"direction":"\u003e","locations":"Membrane; Multi-pass membrane protein","altext":"4,4-dimethyl-5-alpha-cholesta-8,24-dien-3-beta-ol + NADP(+) = 4,4-dimethyl-5-alpha-cholesta-8,14,24-trien-3-beta-ol + NADPH.","export":false,"pw_reaction_id":null,"source":null},{"id":14388,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006898","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"14-34;72-90;110-127;148-172;243-263;309-328;369-387","pdb_id":null,"cellular_location":"Membrane; Multi-pass membrane protein","genbank_gene_id":"M99419","genbank_protein_id":"171143","gene_card_id":"ERG24","chromosome_location":"chromosome 14","locus":"YNL280C","synonyms":["C-14 sterol reductase","Sterol C14-reductase"],"enzyme_classes":["1.3.1.70"],"go_classes":[{"category":"Component","description":" membrane"},{"category":"Component","description":" cell part"},{"category":"Function","description":" Not Available"},{"category":"Process","description":" Not Available"}],"pfams":[{"name":"ERG4_ERG24","identifier":"PF01222"}],"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":"ATGGTATCAGCTTTGAATCCCAGAACTACAGAGTTTGAATTTGGTGGGCTGATTGGTGCCTTAGGCATCAGCATAGGGCTGCCTGTTTTCACTATCATCTTGAATCAAATGATAAGGCCCGATTATTTTATTAAGGGATTTTTCCAGAATTTCGATATAGTTGAGCTTTGGAACGGTATCAAGCCATTGCGCTACTATCTGGGCAATCGTGAATTATGGACTGTCTATTGCCTGTGGTATGGAATACTGGCAGTTTTGGACGTCATTTTACCGGGCAGAGTCATGAAGGGTGTTCAGTTAAGGGATGGTTCGAAGCTTTCGTATAAGATCAATGGAATTGCCATGTCTACAACTTTGGTCTTAGTTTTGGCTATCAGATGGAAATTGACTGATGGACAATTGCCTGAATTGCAATATCTGTATGAAAATCACGTTAGTTTATGCATAATATCTATTTTGTTTTCGTTCTTTTTGGCGACGTACTGCTATGTTGCCAGCTTCATACCATTGATCTTCAAGAAAAATGGTAATGGCAAAAGGGAAAAGATCTTAGCACTAGGTGGAAATTCAGGAAACATCATTTACGATTGGTTTATTGGTAGAGAACTGAACCCTCGTCTCGGCCCATTAGATATCAAGATGTTTTCAGAGTTGAGACCCGGCATGTTGTTATGGTTACTGATCAATCTTTCCTGTCTGCATCACCATTACCTGAAGACTGGTAAAATCAACGATGCATTGGTCTTGGTTAATTTCTTGCAAGGATTTTACATTTTCGATGGAGTACTAAACGAGGAAGGTGTATTAACCATGATGGATATCACTACAGATGGGTTTGGTTTCATGCTAGCGTTTGGTGACTTAAGTTTAGTTCCATTCACCTACTCATTACAAGCGCGTTACTTGAGTGTTTCCCCTGTGGAATTGGGATGGGTGAAAGTTGTCGGTATATTAGCCATAATGTTTTTGGGTTTCCACATCTTCCACTCGGCAAATAAGCAAAAATCTGAGTTTAGACAAGGTAAATTAGAAAATCTAAAAAGTATTCAGACAAAGCGTGGTACAAAGTTATTATGTGACGGGTGGTGGGCTAAATCACAGCATATCAATTACTTTGGCGATTGGCTGATTTCATTAAGTTGGTGTTTGGCCACCTGGTTCCAAACTCCCTTGACATATTACTACTCGTTGTACTTCGCCACGTTGTTATTACACCGTCAACAACGTGATGAGCACAAGTGCCGCCTGAAATATGGCGAAAATTGGGAAGAATACGAAAGAAAAGTTCCTTACAAGATCATTCCATATGTTTATTAA","protein_sequence":"MVSALNPRTTEFEFGGLIGALGISIGLPVFTIILNQMIRPDYFIKGFFQNFDIVELWNGIKPLRYYLGNRELWTVYCLWYGILAVLDVILPGRVMKGVQLRDGSKLSYKINGIAMSTTLVLVLAIRWKLTDGQLPELQYLYENHVSLCIISILFSFFLATYCYVASFIPLIFKKNGNGKREKILALGGNSGNIIYDWFIGRELNPRLGPLDIKMFSELRPGMLLWLLINLSCLHHHYLKTGKINDALVLVNFLQGFYIFDGVLNEEGVLTMMDITTDGFGFMLAFGDLSLVPFTYSLQARYLSVSPVELGWVKVVGILAIMFLGFHIFHSANKQKSEFRQGKLENLKSIQTKRGTKLLCDGWWAKSQHINYFGDWLISLSWCLATWFQTPLTYYYSLYFATLLLHRQQRDEHKCRLKYGENWEEYERKVPYKIIPYVY"}]}