Showing metabocard for DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) (BMDB0007230)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:33:11 UTC
Update Date2020-05-21 16:27:52 UTC
BMDB IDBMDB0007230
Secondary Accession Numbers
  • BMDB07230
Metabolite Identification
Common NameDG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)
DescriptionDG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2], also known as dg(18:1(9z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2] or DAG(18:1/20:5), belongs to the class of organic compounds known as 1,2-dg(18:1(9z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s. These are dg(18:1(9z)/20:5(5z,8z,11z,14z,17z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:2(13Z,16Z)) pathway and de novo triacylglycerol biosynthesis TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/24:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(18:1/20:5)Lipid Annotator, HMDB
DAG(38:6)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0)Lipid Annotator
DG(38:6)Lipid Annotator, HMDB
1-oleoyl-2-eicosapentaenoyl-sn-glycerolLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DG(18:1/20:5)Lipid Annotator, HMDB
Diacylglycerol(18:1/20:5)Lipid Annotator, HMDB
1-(9Z-octadecenoyl)-2-(5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycerolLipid Annotator, HMDB
Diacylglycerol(38:6)Lipid Annotator, HMDB
Chemical FormulaC41H68O5
Average Molecular Weight640.9756
Monoisotopic Molecular Weight640.506675286
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C41H68O5/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/h5,7,11,13,17-19,21-22,24,28,30,39,42H,3-4,6,8-10,12,14-16,20,23,25-27,29,31-38H2,1-2H3/b7-5-,13-11-,19-17-,21-18-,24-22-,30-28-/t39-/m0/s1
InChI KeyJLJZWBKQVKCOJP-GZAZVFSZSA-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 Descriptors
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
logP9.28ALOGPS
logP12.5ChemAxon
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 Count34ChemAxon
Refractivity202 m³·mol⁻¹ChemAxon
Polarizability79.62 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, Positivesplash10-0550-3294010000-1e1c59bb61b83791ec3fView 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(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-059l-1098005000-a0135e782c774967c57eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2094001000-684192c98241acdc5e9cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-1092020000-e809e4561a2fa7eff576View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01qi-0095003000-1a3d14f8f7c66b7db3c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1093000000-f02d93a6f7981d986b73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-3092000000-f707b7204cb9d38d7247View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052o-3096058000-ee5f43bb7e9d8187d03aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-1193000000-3a1a0f70c5309a24927aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1296000000-80492e89905b24f801e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-e8086b36c3df6f24dd64View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0009000000-27d5b6d9dd04bde704a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0045009000-3bdcc6ff0fd12dad7fa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01x0-4095001000-fd2fe1a67e74412cb36cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0lz9-3192000000-dbb9bc8418300cb73b21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-0697d21e1d6f73bcdbfeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0abi-0009004000-362e41d13bed8df166c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-0009004000-2a69aebf8acdb4bb73c9View 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 IDHMDB0007230
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822747
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543797
PDB IDNot Available
ChEBI IDNot Available
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(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) → Cytidine monophosphate + PE(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z))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(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Erucoyl-CoA → TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:1(13Z)) + Coenzyme Adetails
DG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/0:0) + Clupanodonyl CoA → TG(18:1(9Z)/20:5(5Z,8Z,11Z,14Z,17Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails