1.0 2016-09-30 23:32:56 UTC 2020-06-04 20:21:04 UTC BMDB0007218 BMDB07218 DG(18:1(9Z)/18:1(9Z)/0:0) DG(18:1(9Z)/18:1(9Z)/0:0), also known as sn-1,2-dioleoylglycerol or sn-1,2-diolein, belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(18:1(9Z)/18:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:1(9Z)/18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:1(9Z)/18:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(18:1(9Z)/18:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:1(9Z)/18:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z)) pathway. 1,2-Di-(9Z-octadecenoyl)-sn-glycerol DG(18:1/18:1/0:0) sn-1,2-Diolein sn-1,2-Dioleoylglycerol 1,2-Dioleoyl-rac-glycerol Di-oleoylglycerol Glycerol dioleate Diolein Dioleoylglycerol 1,2-Dioleoylglycerol Diacylglycerol(36:2) DG(18:1/18:1) DG(36:2) DAG(36:2) Diglyceride Diacylglycerol(18:1/18:1) Diacylglycerol DAG(18:1/18:1) 1,2-Di(9Z-octadecenoyl)-rac-glycerol (+--)-1,2-Dioleoylglycerol 1,2-Diolein 9-Octadecenoic acid (9Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester Glyceryl 1,2-dioleate 9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester 1,2-Glyceryl dioleate (+--)-1,2-Diolein 1,2-Dioleoyl-DL-glycerol 9-Octadecenoic acid (9Z)-, 1,1'-(1-(hydroxymethyl)-1,2-ethanediyl) ester 9-Octadecenoic acid (9Z)-, diester with 1,2,3-propanetriol Oleic acid diglyceride DG(18:1(9Z)/18:1(9Z)/0:0) C39H72O5 620.986 620.537975414 (2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate 1,2-dioleoyl-sn-glycerol 24529-88-2 [H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1 AFSHUZFNMVJNKX-LLWMBOQKSA-N belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Organic compounds Lipids and lipid-like molecules Glycerolipids Diradylglycerols 1,2-diacylglycerols Carbonyl compounds Carboxylic acid esters Dicarboxylic acids and derivatives Fatty acid esters Hydrocarbon derivatives Organic oxides Primary alcohols 1,2-acyl-sn-glycerol Alcohol Aliphatic acyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Fatty acid ester Fatty acyl Hydrocarbon derivative Organic oxide Organic oxygen compound Organooxygen compound Primary alcohol Aliphatic acyclic compounds 1,2-diacyl-sn-glycerol Diacylglycerols dioleoylglycerol Solid logp 10.26 ALOGPS logs -7.70 ALOGPS logp 13.06 ChemAxon pka_strongest_acidic 14.58 ChemAxon pka_strongest_basic -3 ChemAxon iupac (2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate ChemAxon average_mass 620.986 ChemAxon mono_mass 620.537975414 ChemAxon smiles [H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC ChemAxon formula C39H72O5 ChemAxon inchi InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1 ChemAxon inchikey AFSHUZFNMVJNKX-LLWMBOQKSA-N ChemAxon polar_surface_area 72.83 ChemAxon refractivity 188.34 ChemAxon polarizability 80.99 ChemAxon rotatable_bond_count 36 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon number_of_rings 0 ChemAxon bioavailability 0 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:1(9Z)) SMP0075126 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:2(9Z,12Z)) SMP0075127 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(6Z,9Z,12Z)) SMP0075128 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:3(9Z,12Z,15Z)) SMP0075129 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/18:4(6Z,9Z,12Z,15Z)) SMP0075130 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:0) SMP0075131 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:1(11Z)) SMP0075132 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:2(11Z,14Z)) SMP0075133 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(5Z,8Z,11Z)) SMP0075134 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:3(8Z,11Z,14Z)) SMP0075135 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) SMP0075136 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:4(8Z,11Z,14Z,17Z)) SMP0075137 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)) SMP0075138 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:0) SMP0075139 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:1(13Z)) SMP0075140 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:2(13Z,16Z)) SMP0075141 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:4(7Z,10Z,13Z,16Z)) SMP0075142 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)) SMP0075143 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:5(7Z,10Z,13Z,16Z,19Z)) SMP0075144 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) SMP0075145 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:0) SMP0075146 De Novo Triacylglycerol Biosynthesis TG(18:1(9Z)/18:1(9Z)/24:1(15Z)) SMP0075147 Phosphatidylcholine Biosynthesis PC(18:1(9Z)/18:1(9Z)) SMP0080612 Phosphatidylethanolamine Biosynthesis PE(18:1(9Z)/18:1(9Z)) SMP0082416 Specdb::CMs 39297 Specdb::CMs 544302 Specdb::CMs 792808 Specdb::MsMs 633250 Specdb::MsMs 633251 Specdb::MsMs 633252 Specdb::MsMs 1474548 Specdb::MsMs 1474549 Specdb::MsMs 1474550 Specdb::MsMs 1478906 Specdb::MsMs 1478907 Specdb::MsMs 1478908 Specdb::MsMs 1478909 Specdb::MsMs 1478910 Specdb::MsMs 1478911 Specdb::MsMs 1478912 Specdb::MsMs 1478913 Specdb::MsMs 1478914 Specdb::MsMs 1478915 Specdb::MsMs 1478916 Specdb::MsMs 1478917 Specdb::MsMs 1478918 Specdb::MsMs 1478919 Specdb::MsMs 1478920 Specdb::MsMs 1478921 Specdb::MsMs 1478922 Specdb::MsMs 1478923 Specdb::MsMs 1478924 All Tissues Wishart DS, Feunang YD, Marcu A, Guo AC, Liang K, Vazquez-Fresno R, Sajed T, Johnson D, Li C, Karu N, Sayeeda Z, Lo E, Assempour N, Berjanskii M, Singhal S, Arndt D, Liang Y, Badran H, Grant J, Serra-Cayuela A, Liu Y, Mandal R, Neveu V, Pon A, Knox C, Wilson M, Manach C, Scalbert A: HMDB 4.0: the human metabolome database for 2018. Nucleic Acids Res. 2018 Jan 4;46(D1):D608-D617. doi: 10.1093/nar/gkx1089. 29140435 Milk 25 +/- 2 uM Commercial 1% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 55 +/- 4 uM Commercial 2% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 118 +/- 3 uM Commercial 3.25% milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 Milk 2.6 +/- 0.1 uM Commercial skim milk by LC-HRMS Foroutan A, Guo AC, Vazquez-Fresno R, Lipfert M, Zhang L, Zheng J, Badran H, Budinski Z, Mandal R, Ametaj BN, Wishart DS: Chemical Composition of Commercial Cow's Milk. J Agric Food Chem. 2019 Apr 17. doi: 10.1021/acs.jafc.9b00204. 30994344 9543716 FDB094043 52333 A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation) BMDBP00391 Ethanolaminephosphotransferase 1 Q17QM4 SELENOI Enzyme BMDBP02833 Lipin 1 E1BPE8 LPIN1 Enzyme BMDBP02834 Diacylglycerol O-acyltransferase 1 Q8MK44 DGAT1 Enzyme