Showing metabocard for DG(16:1(9Z)/18:2(9Z,12Z)/0:0)[iso2] (BMDB0062623)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2018-08-29 17:08:55 UTC
Update Date2020-06-04 19:49:42 UTC
BMDB IDBMDB0062623
Secondary Accession Numbers
  • BMDB62623
Metabolite Identification
Common NameDG(16:1(9Z)/18:2(9Z,12Z)/0:0)[iso2]
DescriptionDG(16:1(9Z)/18:2(9Z,12Z)/0:0), also known as DAG(16:1N7/18:2N6) or diacylglycerol(16:1/18:2), belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, DG(16:1(9Z)/18:2(9Z,12Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/18:2(9Z,12Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/18:2(9Z,12Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(16:1(9Z)/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PE(16:1(9Z)/18:2(9Z,12Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(16:1(9Z)/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PC(16:1(9Z)/18:2(9Z,12Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(16:1(9Z)/18:2(9Z,12Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:1(9Z)/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2R)-1-[(9Z)-Hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoic acidGenerator
Chemical FormulaC37H66O5
Average Molecular Weight590.93
Monoisotopic Molecular Weight590.491025225
IUPAC Name(2R)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Name(2R)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
CAS Registry NumberNot Available
SMILES
[H][C@@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H66O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,35,38H,3-10,12,15,19-34H2,1-2H3/b13-11-,16-14-,18-17-/t35-/m1/s1
InChI KeyBHGPPCIWDXQOMA-AXXPJHFTSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassLineolic acids and derivatives
Direct ParentLineolic acids and derivatives
Alternative Parents
Substituents
  • Octadecanoid
  • Diradylglycerol
  • Diacylglycerol
  • 1,2-acyl-sn-glycerol
  • Glycerolipid
  • Fatty acid ester
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
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
logP9.73ALOGPS
logP11.81ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity180.25 m³·mol⁻¹ChemAxon
Polarizability76.04 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9i-0092020000-cca0703ff0bfec80e64dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udr-1092000000-e06483da5cb084a5cfdfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-1170-2090000000-31dd9c72b44486dd6e7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-1095040000-0c72849bc7b3256a0031View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1093110000-6de66a23e847b22a43f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-1291320000-78ce4f1e800301151d9eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
MilkDetected and Quantified2.3 +/- 0.2 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified3.3 +/- 0.1 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified4.6 +/- 0.3 uMNot SpecifiedNot Specified
Normal		 details
MilkDetected and Quantified0.96 +/- 0.03 uMNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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.