Showing metabocard for DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) (BMDB0007077)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:30:02 UTC
Update Date2020-05-21 16:27:33 UTC
BMDB IDBMDB0007077
Secondary Accession Numbers
  • BMDB07077
Metabolite Identification
Common NameDG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0)
DescriptionDG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0), also known as dg(15:0/18:4(6z,9z,12z,15z)/0:0) or DAG(15:0/18:4), 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. DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) can be biosynthesized from PA(15:0/18:4(6Z,9Z,12Z,15Z)); which is mediated by the enzyme phosphatidate phosphatase. In addition, DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) and gondoyl-CoA can be converted into TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)); which is mediated by the enzyme dg(15:0/18:4(6z,9z,12z,15z)/0:0) O-acyltransferase. In cattle, DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Pentadecanoyl-2-stearidonoyl-sn-glycerolHMDB
DAG(15:0/18:4)HMDB
DAG(15:0/18:4N3)HMDB
DAG(15:0/18:4W3)HMDB
DAG(33:4)HMDB
DG(15:0/18:4)HMDB
DG(15:0/18:4N3)HMDB
DG(15:0/18:4W3)HMDB
DG(33:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(15:0/18:4)HMDB
Diacylglycerol(15:0/18:4n3)HMDB
Diacylglycerol(15:0/18:4W3)HMDB
Diacylglycerol(33:4)HMDB
DiglycerideHMDB
1-Pentadecanoyl-2-(6Z,9Z,12Z,15Z-octadecatetraenoyl)-sn-glycerolHMDB
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC36H62O5
Average Molecular Weight574.8745
Monoisotopic Molecular Weight574.459725094
IUPAC Name(2S)-1-hydroxy-3-(pentadecanoyloxy)propan-2-yl (6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCC)OC(=O)CCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C36H62O5/c1-3-5-7-9-11-13-15-17-18-19-21-23-25-27-29-31-36(39)41-34(32-37)33-40-35(38)30-28-26-24-22-20-16-14-12-10-8-6-4-2/h5,7,11,13,17-18,21,23,34,37H,3-4,6,8-10,12,14-16,19-20,22,24-33H2,1-2H3/b7-5-,13-11-,18-17-,23-21-/t34-/m0/s1
InChI KeyMFIONIMKDOSXCC-SJQSLJDISA-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 DescriptorsNot Available
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
logP9.15ALOGPS
logP11ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity176.77 m³·mol⁻¹ChemAxon
Polarizability71.85 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, Positivesplash10-001s-5952103000-b9eb97ddd260cb401266View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(15:0/18:4(6Z,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, Positivesplash10-0006-0000090000-d00b40f8b20e67bd5401View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053t-0099090000-5324571b98021357dca9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001n-0099090000-99bd0fd82a61c4869d74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-3286490000-3bc0cab8e1ce0b6db869View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-4194020000-353d8a68a42511673b6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-5698000000-324f8c5569783470f43eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1063090000-b3b2c2a95da936efd79dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-2091000000-5b11b23ceba23d9a9d75View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05dl-2190000000-73301cd22b1a74017478View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000090000-700d22d9bc99b44381d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053t-0088090000-1894d7572da2587baf88View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001n-0088090000-bc5efc6b202bd0ebc867View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000090000-279b912e33a99e4f0835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000090000-279b912e33a99e4f0835View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ai0-0019000000-dd669cb252cc3d3f138cView 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 IDHMDB0007077
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024271
KNApSAcK IDNot Available
Chemspider ID24765910
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478006
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(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(15:0/18:4(6Z,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(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:0) + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails
DG(15:0/18:4(6Z,9Z,12Z,15Z)/0:0) + Tetracosanoyl-CoA → TG(15:0/18:4(6Z,9Z,12Z,15Z)/24:0) + Coenzyme Adetails