Showing metabocard for DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007255)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:41 UTC
Update Date2020-05-21 16:27:53 UTC
BMDB IDBMDB0007255
Secondary Accession Numbers
  • BMDB07255
Metabolite Identification
Common NameDG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0), also known as DAG(18:2/20:3) or dg(18:2(9z,12z)/20:3(5z,8z,11z)/0:0), belongs to the class of organic compounds known as 1,2-dg(18:2(9z,12z)/20:3(5z,8z,11z)/0:0)s. These are dg(18:2(9z,12z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) and arachidonyl-CoA can be converted into TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme dg(18:2(9z,12z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidate phosphatase. Furthermore, DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) and docosadienoyl-CoA can be converted into TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) through its interaction with the enzyme dg(18:2(9z,12z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Finally, CDP-Ethanolamine and DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) can be converted into cytidine monophosphate and PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) pathway, de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:2(13Z,16Z)) pathway, and phosphatidylethanolamine biosynthesis pe(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(18:2/20:3)HMDB
DG(18:2/20:3)HMDB
1-Linoleoyl-2-meadoyl-sn-glycerolHMDB
DG(38:5)HMDB
DAG(38:5)HMDB
Diacylglycerol(38:5)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:2/20:3)HMDB
1-(9Z,12Z-Octadecadienoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycerolHMDB
DiglycerideHMDB
DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC41H70O5
Average Molecular Weight642.9915
Monoisotopic Molecular Weight642.52232535
IUPAC Name(2S)-1-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H70O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h12,14,17-19,21-22,24,28,30,39,42H,3-11,13,15-16,20,23,25-27,29,31-38H2,1-2H3/b14-12-,19-17-,21-18-,24-22-,30-28-/t39-/m0/s1
InChI KeyHGZIMBMJGQIUGE-VUKZTOICSA-N
Chemical Taxonomy
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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • 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
logP9.81ALOGPS
logP12.86ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity200.89 m³·mol⁻¹ChemAxon
Polarizability81.09 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 (Non-derivatized) - 70eV, Positivesplash10-01p9-2295340000-041272ed85f83599348dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06rl-1098005000-f801d46e5271c70ea869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1093111000-d2af4d299c0e2c1b9657View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01w1-1091120000-ab831f42e019d009e16fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vu-0096003000-f3253cb82910857670a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-1093000000-5430a1085a5a31d86a3aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06vr-3092000000-d7eb2de7a5a7987abe99View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f96-3059008000-6ed24c2d4eb9f12dc8d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0729-5095001000-fbcc400e00f60cb09f73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3093000000-d3d1b8d38a7f9386364fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-25d712cfd42c783e22f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-25d712cfd42c783e22f2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a50-0009000000-6f36b9a1b7d442e44fa1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000f-4274049000-2a91edc3cee9fad40329View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2393000000-fe68e7e88dd1492e4aa3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-3497110000-c662d5003d92d6162a3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-c42d84986800260de203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03g0-0009004000-01afe348e95de3e9a402View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-0009004000-22e456971b44d3f346d3View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • 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 IDHMDB0007255
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024448
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478107
PDB IDNot Available
ChEBI ID89201
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(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(18:2(9Z,12Z)/20:3(5Z,8Z,11Z))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(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(18:2(9Z,12Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails