Showing metabocard for DG(16:1(9Z)/18:2(9Z,12Z)/0:0) (BMDB0007132)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:13 UTC
Update Date2020-05-21 16:27:43 UTC
BMDB IDBMDB0007132
Secondary Accession Numbers
  • BMDB07132
Metabolite Identification
Common NameDG(16:1(9Z)/18:2(9Z,12Z)/0:0)
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
1-(9Z-Hexadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycerolChEBI
DAG(16:1/18:2)ChEBI
DAG(16:1N7/18:2N6)ChEBI
DAG(16:1W7/18:2W6)ChEBI
DAG(34:3)ChEBI
DG(16:1/18:2/0:0)ChEBI
DG(16:1N7/18:2N6)ChEBI
Diacylglycerol(16:1/18:2)ChEBI
Diacylglycerol(16:1n7/18:2n6)ChEBI
Diacylglycerol(16:1W7/18:2W6)ChEBI
DiglycerideLipid Annotator, HMDB
1-palmitoleoyl-2-linoleoyl-sn-glycerolLipid Annotator, HMDB
DG(16:1/18:2)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DG(34:3)Lipid Annotator, HMDB
DG(16:1(9Z)/18:2(9Z,12Z)/0:0)Lipid Annotator, ChEBI
Diacylglycerol(34:3)Lipid Annotator, HMDB
DG(16:1W7/18:2W6)HMDB
Chemical FormulaC37H66O5
Average Molecular Weight590.9169
Monoisotopic Molecular Weight590.491025222
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(CO)OC(=O)CCCCCCC\C([H])=C(\[H])C\C([H])=C(\[H])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-/m0/s1
InChI KeyBHGPPCIWDXQOMA-IXDOJJAKSA-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
  • 1,2-acyl-sn-glycerol
  • Diacylglycerol
  • Diradylglycerol
  • Fatty acid ester
  • Glycerolipid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
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
Polarizability75.78 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-000j-5594335000-782876a41569980a55d2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/18:2(9Z,12Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-2c9dba2a539fdca961d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009030000-b5dd00a5b026e56991cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009013000-5e012ead38ae034f476cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-418bfe830d05946bacd1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kr-0009030000-e98c5253301f8d8e759bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009013000-3fc4a6bba23ca4568dabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03du-2059170000-2b6d849e1249e1cb0a18View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-2496020000-4fbbc087e77afe2e9246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9611000000-4b10937945f95bdc7a8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-06c2ad30942913111b60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-8be4d6fe4c260cf31d9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3095040000-52101f58d221b60fcdf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-4093010000-13dbb45097d6eee73bfcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3390000000-d4e793ccdbc0c70f1c8dView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007132
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024326
KNApSAcK IDNot Available
Chemspider ID7822649
KEGG Compound IDC00165
BioCyc IDDIACYLGLYCEROL
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID4319
PubChem Compound9543699
PDB IDNot Available
ChEBI ID84419
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ethanolaminephosphotransferase 1
General function:
Involved in ethanolaminephosphotransferase activity
Specific function:
Catalyzes phosphatidylethanolamine biosynthesis from CDP-ethanolamine. It thereby plays a central role in the formation and maintenance of vesicular membranes. Involved in the foramtion of phosphatidylethanolamine via 'Kennedy' pathway (By similarity).
Gene Name:
SELENOI
Uniprot ID:
Q17QM4
Molecular weight:
45214.0
Reactions
CDP-Ethanolamine + DG(16:1(9Z)/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/18:2(9Z,12Z))details
Enzyme Details
2. Diacylglycerol O-acyltransferase 1
General function:
Not Available
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. In contrast to DGAT2 it is not essential for survival. May be involved in VLDL (very low density lipoprotein) assembly. Functions as the major acyl-CoA retinol acyltransferase (ARAT) in the skin, where it acts to maintain retinoid homeostasis and prevent retinoid toxicity leading to skin and hair disorders. In liver, plays a role in esterifying exogenous fatty acids to glycerol.
Gene Name:
DGAT1
Uniprot ID:
Q8MK44
Molecular weight:
55602.0
Reactions
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Gondoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/20:1(11Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/18:2(9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:2(9Z,12Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails