Showing metabocard for DG(O-16:0/20:4(8E,11E,14E,17E)/0:0) (BMDB0063598)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-09-23 03:10:41 UTC
Update Date2020-06-04 19:33:23 UTC
MCDB ID BMDB0063598
Secondary Accession Numbers
  • BMDB63598
Metabolite Identification
Common NameDG(O-16:0/20:4(8E,11E,14E,17E)/0:0)
DescriptionDG(O-16:0/20:4(8E,11E,14E,17E)/0:0), also referred to as DG(20:4), is a diglyceride which belongs to the family of Diacylglycerols (DAGs). These are glycerolipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. 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. DAGs can have many different combinations of fatty acids attached at the C-1, C-2, or C-3 positions. DG(20:4), in particular, consists of one chain of hexadecyl acid at the C-1 position and one chain of arachidonic acid at the C-2 position. DG(20:4) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway. 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-3 position.
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC39H70O4
Average Molecular Weight602.985
Monoisotopic Molecular Weight602.527410734
IUPAC Name(2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
Traditional Name(2R)-1-(hexadecyloxy)-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COCCCCCCCCCCCCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C39H70O4/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-39(41)43-38(36-40)37-42-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2/h5,7,11,13,17,19,21-22,38,40H,3-4,6,8-10,12,14-16,18,20,23-37H2,1-2H3/b7-5-,13-11-,19-17-,22-21-/t38-/m1/s1
InChI KeyZOQPRIBCWWPWEH-SCBZKDMTSA-N
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.28ALOGPS
logP12.71ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity190.81 m³·mol⁻¹ChemAxon
Polarizability79.23 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f7a-0092023000-b9c065ec1f37848c286e2019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00n1-0191010000-ec22a2ddb50a5ef508402019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-2390020000-e7ae767eb83f84091a002019-02-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0089007000-ea0572e23f3e472f5bf52019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uy3-2095001000-e5e6d63c3b706636158f2019-02-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9f-4093000000-ce8de53f8a4ad9de3c572019-02-23View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified0.70 +/- 0.02 uM details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.