{"ymdb_id":"YMDB00627","created_at":"2011-05-29T18:37:28.000Z","updated_at":"2016-09-08T18:35:42.000Z","name":"1,2-dioleoylglycerol","cas":"2442-61-7","state":null,"melting_point":null,"description":"1,2-Dioleoylglycerol is a diacylglycerol (DG).It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis. Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol. Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase.Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.","experimental_water_solubility":null,"experimental_logp_hydrophobicity":null,"location":"endoplasmic reticulum","synthesis_reference":null,"chebi_id":"52323","hmdb_id":null,"kegg_id":null,"pubchem_id":"5497164","cs_id":"4593734","foodb_id":null,"wikipedia_link":null,"biocyc_id":null,"iupac":"1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate","traditional_iupac":"1,2-diolein","logp":"13.057525128666665","pka":null,"alogps_solubility":"1.25e-05 g/l","alogps_logp":"10.26","alogps_logs":"-7.70","acceptor_count":"3","donor_count":"1","rotatable_bond_count":"36","polar_surface_area":"72.83000000000001","refractivity":"188.33610000000002","polarizability":"80.99104122626909","formal_charge":"0","physiological_charge":"0","pka_strongest_basic":"-2.983477273775563","pka_strongest_acidic":"14.577784010572557","bioavailability":"0","number_of_rings":"0","rule_of_five":"0","ghose_filter":"0","veber_rule":"0","mddr_like_rule":"0","synonyms":["1,2-Diolein","9-octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester"],"pathways":[],"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":3029130,"citation":"Hjelmstad, R. H., Bell, R. M. (1987). \"Mutants of Saccharomyces cerevisiae defective in sn-1,2-diacylglycerol cholinephosphotransferase. Isolation, characterization, and cloning of the CPT1 gene.\" J Biol Chem 262:3909-3917."}],"proteins":[{"created_at":"2011-05-26T18:07:16.000Z","updated_at":"2011-07-22T17:54:27.000Z","name":"Cholinephosphotransferase 1","uniprot_id":"P17898","uniprot_name":"CPT1_YEAST","enzyme":true,"transporter":false,"gene_name":"CPT1","num_residues":393,"molecular_weight":"44829.0","theoretical_pi":"6.57","general_function":"Involved in phosphotransferase activity, for other substituted phosphate groups","specific_function":"Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process","reactions":[{"id":1386,"direction":"\u003c\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":1387,"direction":"\u003e","locations":"endoplasmic reticulum","altext":null,"export":true,"pw_reaction_id":null,"source":null},{"id":2507,"direction":"\u003e","locations":"Microsome membrane; Multi-pass membrane protein; Multi-pass membrane protein. Endoplasmic reticulum membrane","altext":"CDP-choline + 1,2-diacylglycerol = CMP + a phosphatidylcholine.","export":false,"pw_reaction_id":null,"source":null},{"id":14462,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006981","source":"Smpdb"},{"id":14463,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R006984","source":"Smpdb"},{"id":14464,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R007002","source":"Smpdb"},{"id":14465,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047264","source":"Smpdb"},{"id":14466,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047316","source":"Smpdb"},{"id":14467,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047322","source":"Smpdb"},{"id":14468,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047327","source":"Smpdb"},{"id":14469,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047333","source":"Smpdb"},{"id":14470,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047339","source":"Smpdb"},{"id":14471,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047344","source":"Smpdb"},{"id":14472,"direction":"\u003e","locations":null,"altext":null,"export":true,"pw_reaction_id":"PW_R047350","source":"Smpdb"}],"signal_regions":"None","transmembrane_regions":"41-61;173-193;211-231;264-284;286-306;321-341;349-369","pdb_id":null,"cellular_location":"Microsome membrane; Multi-pass membrane protein. Endoplasmic reticulum membrane; Multi-pass membrane protein","genbank_gene_id":"J05203","genbank_protein_id":"171318","gene_card_id":"CPT1","chromosome_location":"chromosome 14","locus":"YNL130C","synonyms":["Diacylglycerol cholinephosphotransferase 1","Sn-1,2-diacylglycerol cholinephosphotransferase","CHOPT"],"enzyme_classes":["2.7.8.2"],"go_classes":[{"category":"Component","description":" cell part"},{"category":"Component","description":" membrane"},{"category":"Function","description":" catalytic activity"},{"category":"Function","description":" transferase activity"},{"category":"Function","description":" transferase activity, transferring phosphorus-containing groups"},{"category":"Function","description":" phosphotransferase activity, for other substituted phosphate groups"},{"category":"Process","description":" metabolic process"},{"category":"Process","description":" organophosphate metabolic process"},{"category":"Process","description":" phospholipid metabolic process"},{"category":"Process","description":" phospholipid biosynthetic process"}],"pfams":[{"name":"CDP-OH_P_transf","identifier":"PF01066"}],"pathways":[{"name":"Glycerophospholipid metabolism","kegg_map_id":"00564"},{"name":"Ether lipid metabolism","kegg_map_id":"00565"},{"name":"Choline metabolism","kegg_map_id":null},{"name":"Lysolipid incorporation into ER","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(10:0/10:0)","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(14:0/14:0)","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(16:0/16:0)","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(16:1(11Z)/16:1(11Z))","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(16:1(9Z)/16:1(9Z))","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(18:0/18:0)","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(18:1(9Z)/18:1(9Z))","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z))","kegg_map_id":null},{"name":"Lysolipid incorporation into ER PC(20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z))","kegg_map_id":null}],"gene_sequence":"ATGGATTCGAAAACAGTATTACTAACTGATTCAGGGGAAACAATGGGATTCTTTATTCCTCAGAGTAGTTTGGGAAACTTGAAGCTTTACAAGTATCAAAGTGATGACCGCTCTTTCCTTTCAAACCATGTATTGAGGCCCTTTTGGAGAAAGTTTGCGACTATTTTTCCACTATGGATGGCACCCAATTTGGTAACATTATTAGGGTTCTGCTTTATTATATTTAATGTGTTAACAACACTTTACTACGACCCGTATTTTGACCAGGAATCGCCACGTTGGACCTATTTCTCCTATGCTATAGGTTTGTTTTTATACCAGACTTTTGATGCTTGCGATGGAATGCATGCACGTCGTACAGGCCAGCAGGGCCCTCTAGGGGAATTGTTTGACCATTGTATTGATTCAATCAACACAACTTTGTCAATGATTCCTGTCTGTTCCATGACAGGTATGGGTTACACATATATGACCATTTTTTCACAATTTGCGATATTGTGCAGCTTTTACTTGAGCACATGGGAAGAGTATCACACCCACAAACTTTATCTAGCTGAATTCTGCGGTCCTGTTGAAGGTATTATTGTTTTGTGTATTTCTTTCATTGCAGTCGGAATTTACGGACCTCAAACCATCTGGCACACTAAAGTAGCGCAATTCTCCTGGCAAGATTTTGTGTTTGATGTTGAAACCGTTCATCTAATGTATGCATTTTGCACAGGAGCATTAATATTTAATATTGTCACAGCTCATACAAACGTCGTGAGGTATTACGAATCCCAATCGACCAAATCTGCAACTCCAAGCAAAACTGCAGAAAATATAAGTAAAGCAGTAAATGGTCTTTTGCCATTCTTTGCATACTTCTCTTCAATTTTTACCTTAGTCTTGATTCAACCATCTTTTATTTCTTTGGCTTTAATTTTATCGATTGGTTTTTCGGTTGCCTTTGTAGTTGGTCGGATGATTATTGCTCATTTAACCATGCAACCATTCCCAATGGTCAATTTCCCATTTTTAATCCCAACTATCCAATTGGTATTGTACGCATTTATGGTTTACGTTTTAGATTACCAAAAAGGAAGCATAGTTTCTGCATTGGTTTGGATGGGACTCGGCTTGACACTTGCTATCCATGGAATGTTCATCAATGATATTATCTATGACATCACTACCTTTCTGGATATTTACGCTTTATCAATTAAACATCCAAAAGAAATTTAG","protein_sequence":"MGFFIPQSSLGNLKLYKYQSDDRSFLSNHVLRPFWRKFATIFPLWMAPNLVTLLGFCFIIFNVLTTLYYDPYFDQESPRWTYFSYAIGLFLYQTFDACDGMHARRTGQQGPLGELFDHCIDSINTTLSMIPVCSMTGMGYTYMTIFSQFAILCSFYLSTWEEYHTHKLYLAEFCGPVEGIIVLCISFIAVGIYGPQTIWHTKVAQFSWQDFVFDVETVHLMYAFCTGALIFNIVTAHTNVVRYYESQSTKSATPSKTAENISKAVNGLLPFFAYFSSIFTLVLIQPSFISLALILSIGFSVAFVVGRMIIAHLTMQPFPMVNFPFLIPTIQLVLYAFMVYVLDYQKGSIVSALVWMGLGLTLAIHGMFINDIIYDITTFLDIYALSIKHPKEI"}]}