Showing metabocard for DG(16:0/18:3(9Z,12Z,15Z)/0:0) (BMDB0007105)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:41 UTC
Update Date2020-05-21 16:27:39 UTC
BMDB IDBMDB0007105
Secondary Accession Numbers
  • BMDB07105
Metabolite Identification
Common NameDG(16:0/18:3(9Z,12Z,15Z)/0:0)
DescriptionDG(16:0/18:3(9Z,12Z,15Z)/0:0), also known as DAG(16:0/18:3) or diacylglycerol(16:0/18:3), 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(16:0/18:3(9Z,12Z,15Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:0/18:3(9Z,12Z,15Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(16:0/18:3)Lipid Annotator, HMDB
1-palmitoyl-2-a-linolenoyl-sn-glycerolLipid Annotator, HMDB
DG(16:0/18:3)Lipid Annotator, HMDB
DG(16:0/18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
DiglycerideLipid Annotator, HMDB
Diacylglycerol(16:0/18:3)Lipid Annotator, HMDB
DAG(34:3)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DG(34:3)Lipid Annotator, HMDB
1-hexadecanoyl-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerolLipid Annotator, HMDB
Diacylglycerol(34:3)Lipid Annotator, HMDB
Chemical FormulaC37H66O5
Average Molecular Weight590.9169
Monoisotopic Molecular Weight590.491025222
IUPAC Name(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CC)=C(/[H])C\C([H])=C(\[H])C\C([H])=C(\[H])CCCCCCCC(=O)O[C@@]([H])(CO)COC(=O)CCCCCCCCCCCCCCC
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/h5,7,11,13,17-18,35,38H,3-4,6,8-10,12,14-16,19-34H2,1-2H3/b7-5-,13-11-,18-17-/t35-/m0/s1
InChI KeyUHPKYXAUVQOHQL-DSZXWZEOSA-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
logP9.79ALOGPS
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
Polarizability74.79 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, Positivesplash10-03dj-5492103000-d9492d76bbd94477fd09View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:0/18:3(9Z,12Z,15Z)/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-0009030000-6d3823ea5e5e30c2e278View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009013000-f02bd6bc82186632d789View 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-d5126a3094a7234981e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g9-0009013000-9683375c1a7e345b5fc1View 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, Positivesplash10-0a50-0009000000-764d62ab96e8196e5e1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01p6-2227090000-44a50a26261cf741e121View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-7893010000-63e68e91c35471216941View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00lu-9400000000-6ae888f7ae187c38704fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0570-2096050000-e3cea41777ac7b71916bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-3093010000-204f8361ee7e74332550View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a70-1191000000-2c262191b605fbd171bbView 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 IDHMDB0007105
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7822650
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543700
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(16:0/18:3(9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(16:0/18:3(9Z,12Z,15Z))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(16:0/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/22:0) + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(16:0/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(16:0/18:3(9Z,12Z,15Z)/0:0) + Tetracosanoyl-CoA → TG(16:0/18:3(9Z,12Z,15Z)/24:0) + Coenzyme Adetails