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Showing Compound DG(20:2(11Z,14Z)/22:0/0:0) (FDB024627)

Record Information
Version1.0
Creation date2011-09-21 00:46:50 UTC
Update date2019-11-26 03:21:14 UTC
Primary IDFDB024627
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDG(20:2(11Z,14Z)/22:0/0:0)
DescriptionDG(20:2(11Z,14Z)/22:0/0:0) is a diglyceride, or a diacylglycerol (DAG). 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. DG(20:2(11Z,14Z)/22:0/0:0), in particular, consists of one chain of eicosadienoic acid at the C-1 position and one chain of behenic acid at the C-2 position. The eicosadienoic acid moiety is derived from fish oils and liver, while the behenic acid moiety is derived from groundnut oil. 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 (usually in the cytoplasm of liver or adipose tissue cells). 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
1-eicosadienoyl-2-behenoyl-sn-glycerolhmdb
DAG(20:2/22:0)hmdb
DAG(20:2n6/22:0)hmdb
DAG(20:2w6/22:0)hmdb
DG(20:2/22:0)hmdb
DG(20:2n6/22:0)hmdb
DG(20:2w6/22:0)hmdb
Diacylglycerol(20:2/22:0)hmdb
Diacylglycerol(20:2n6/22:0)hmdb
Diacylglycerol(20:2w6/22:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility9.5e-06 g/LALOGPS
logP10.76ALOGPS
logP15.72ChemAxon
logS-7.9ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity215.94 m³·mol⁻¹ChemAxon
Polarizability93.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC45H84O5
IUPAC name(2S)-1-hydroxy-3-(icosa-11,14-dienoyloxy)propan-2-yl docosanoate
InChI IdentifierInChI=1S/C45H84O5/c1-3-5-7-9-11-13-15-17-19-21-22-24-26-28-30-32-34-36-38-40-45(48)50-43(41-46)42-49-44(47)39-37-35-33-31-29-27-25-23-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,43,46H,3-11,13,15-17,19,21-42H2,1-2H3/t43-/m0/s1
InChI KeyKVPLVJYCAJVIFI-QLKFWGTOSA-N
Isomeric SMILES[H][C@](CO)(COC(=O)CCCCCCCCCC=CCC=CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
Average Molecular Weight705.1455
Monoisotopic Molecular Weight704.631875798
Classification
Description Belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
SpectraNot Available
ChemSpider ID7822834
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID9543884
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB07434
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Diacylglycerol O-acyltransferase 1DGAT1O75907
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Diacylglycerol O-acyltransferase 2DGAT2Q96PD7
2-acylglycerol O-acyltransferase 1MOGAT1Q96PD6
2-acylglycerol O-acyltransferase 3MOGAT3Q86VF5
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
Choline-phosphate cytidylyltransferase APCYT1AP49585
Acyl-CoA wax alcohol acyltransferase 2AWAT2Q6E213
Acyl-CoA wax alcohol acyltransferase 1AWAT1Q58HT5
Galactosylceramide sulfotransferaseGAL3ST1Q99999
Phosphatidate cytidylyltransferase 2CDS2O95674
Phosphatidylcholine:ceramide cholinephosphotransferase 2SGMS2Q8NHU3
Phosphatidylcholine:ceramide cholinephosphotransferase 1SGMS1Q86VZ5
Diacylglycerol O-acyltransferase 2-like protein 6DGAT2L6Q6ZPD8
Putative diacylglycerol O-acyltransferase 2-like protein 7DGAT2L7Q6IED9
CDC42 binding protein kinase beta (DMPK-like)CDC42BPBA9JR72
Kinase suppressor of Ras 2KSR2Q6VAB6
Tensin-like C1 domain-containing phosphataseTENC1Q63HR2
Kinase suppressor of Ras 1KSR1Q8IVT5
CDC42-binding protein kinase betaCDC42BPAQ8IWQ7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference