Showing metabocard for DG(18:0/18:2(9Z,12Z)/0:0) (BMDB0007161)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:48 UTC
Update Date2020-05-21 16:27:46 UTC
BMDB IDBMDB0007161
Secondary Accession Numbers
  • BMDB07161
Metabolite Identification
Common NameDG(18:0/18:2(9Z,12Z)/0:0)
DescriptionDG(18:0/18:2(9Z,12Z)/0:0), also known as DAG(18:0/18:2) or diacylglycerol(18:0/18:2), 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(18:0/18:2(9Z,12Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/18:2(9Z,12Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/18:2(9Z,12Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:0/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PE(18:0/18:2(9Z,12Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:0/18:2(9Z,12Z)/0:0) can be converted into cytidine monophosphate and PC(18:0/18:2(9Z,12Z)); which is mediated by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:0/18:2(9Z,12Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/18:2(9Z,12Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoateHMDB
1,2-DG 18:0/18:2(omega-6)HMDB
1-Octadecanoyl-2-(9Z,12Z)-octadecadienoyl-sn-glycerolHMDB
1-Octadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycerolHMDB
DAG(18:0/18:2)HMDB
DAG(18:0/18:2N6)HMDB
DAG(18:0/18:2OMEGA6)HMDB
DAG(36:2)HMDB
DG(18:0/18:2)HMDB
DG(18:0/18:2/0:0)HMDB
DG(18:0/18:2N6)HMDB
DG(18:0/18:2OMEGA6)HMDB
DG(36:2)HMDB
Diacylglycerol(18:0/18:2)HMDB
Diacylglycerol(18:0/18:2n6)HMDB
Diacylglycerol(18:0/18:2omega6)HMDB
Diacylglycerol(36:2)HMDB
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoic acidHMDB
1,2-sn-SLDGHMDB
DiglycerideHMDB
1-Stearoyl-2-linoleoyl-sn-glycerolHMDB
DiacylglycerolHMDB
DG(18:0/18:2(9Z,12Z)/0:0)Lipid Annotator, ChEBI
Chemical FormulaC39H72O5
Average Molecular Weight620.986
Monoisotopic Molecular Weight620.537975414
IUPAC Name(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCC)=C(/[H])C\C([H])=C(\[H])CCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h12,14,18,20,37,40H,3-11,13,15-17,19,21-36H2,1-2H3/b14-12-,20-18-/t37-/m0/s1
InChI KeyAJMZUFBKADIAKC-SKTOPKGQSA-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
logP10.28ALOGPS
logP13.06ChemAxon
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 Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability80.21 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, Positivesplash10-01p9-4390405000-3fe1427c1d097fdcadedView in MoNA
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(18:0/18:2(9Z,12Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-9185b686832caa4f55c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7c-0009004000-bdf4e07ab0b3c9b039d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0009004000-e4beb28e0816ab07d059View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-84cf426a5bd9b351e99aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-84cf426a5bd9b351e99aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bt9-0009000000-2ec8e524e239afaf232eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05r0-2095004000-68af8cdebdf84102c4e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00o0-3094001000-bf9a1a366b52202b20a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o0-1191000000-645eadf5750f86917b26View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-2257009000-715390339d1c76717439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pn-3972001000-9b57eb5e14caf648006aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003v-9300000000-badfd99147ce08c6675aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-203520884a3c62e5734fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7c-0009004000-90e8a9a1b33fffb2c0f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-0009004000-8f40338ba28f7161537aView 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 IDHMDB0007161
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024355
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6441562
PDB IDNot Available
ChEBI ID77097
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(18:0/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(18:0/18:2(9Z,12Z))details
Enzyme Details
2. Lipin 1
General function:
Not Available
Specific function:
Not Available
Gene Name:
LPIN1
Uniprot ID:
E1BPE8
Molecular weight:
102857.0
Reactions
PA(18:0/18:2(9Z,12Z)) + Water → DG(18:0/18:2(9Z,12Z)/0:0) + Hydrogen phosphatedetails
Enzyme Details
3. 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(18:0/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:2(9Z,12Z)/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(18:0/18:2(9Z,12Z)/20:0) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Gondoyl-CoA → TG(18:0/18:2(9Z,12Z)/20:1(11Z)) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:0/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Docosanoyl-CoA → TG(18:0/18:2(9Z,12Z)/22:0) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Erucoyl-CoA → TG(18:0/18:2(9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Clupanodonyl CoA → TG(18:0/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(18:0/18:2(9Z,12Z)/0:0) + Tetracosanoyl-CoA → TG(18:0/18:2(9Z,12Z)/24:0) + Coenzyme Adetails