Showing metabocard for DG(14:1(9Z)/18:2(9Z,12Z)/0:0) (BMDB0007045)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:24 UTC
Update Date2020-05-21 16:27:27 UTC
BMDB IDBMDB0007045
Secondary Accession Numbers
  • BMDB07045
Metabolite Identification
Common NameDG(14:1(9Z)/18:2(9Z,12Z)/0:0)
DescriptionDG(14:1(9Z)/18:2(9Z,12Z)/0:0)[iso2], also known as dg(14:1(9z)/18:2(9z,12z)/0:0)[iso2] or DAG(14:1/18:2), 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(14:1(9Z)/18:2(9Z,12Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/18:2(9Z,12Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(14:1(9Z)/18:2(9Z,12Z)/0:0)[iso2] is involved in a few metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:0) pathway, de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) pathway, and de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:2(9Z,12Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Myristoleoyl-2-linoleoyl-sn-glycerolHMDB
DAG(14:1/18:2)HMDB
DAG(14:1N5/18:2N6)HMDB
DAG(14:1W5/18:2W6)HMDB
DAG(32:3)HMDB
DG(14:1/18:2)HMDB
DG(14:1N5/18:2N6)HMDB
DG(14:1W5/18:2W6)HMDB
DG(32:3)HMDB
DiacylglycerolHMDB
Diacylglycerol(14:1/18:2)HMDB
Diacylglycerol(14:1n5/18:2n6)HMDB
Diacylglycerol(14:1W5/18:2W6)HMDB
Diacylglycerol(32:3)HMDB
DiglycerideHMDB
1-(9Z-Tetradecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycerolHMDB
DG(14:1(9Z)/18:2(9Z,12Z)/0:0)Lipid Annotator
Chemical FormulaC35H62O5
Average Molecular Weight562.8638
Monoisotopic Molecular Weight562.459725094
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (9Z,12Z)-octadeca-9,12-dienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C35H62O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h10-13,16-17,33,36H,3-9,14-15,18-32H2,1-2H3/b12-10-,13-11-,17-16-/t33-/m0/s1
InChI KeyCJKXGRSGRKUWTH-LBWIYNPJSA-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
logP9.29ALOGPS
logP10.92ChemAxon
logS-7.5ALOGPS
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
Refractivity171.05 m³·mol⁻¹ChemAxon
Polarizability70.91 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, Positivesplash10-0avr-8695364000-5a50316bb37304c96071View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/18:2(9Z,12Z)/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, Positivesplash10-001i-0000090000-7aed8b8592e84c17ad87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0099090000-4020f9fb6965cb38a6f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0099090000-7e12f9f6e8306a5882e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3494580000-96e36433d90cad2c7b74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-2692000000-4c52749183288467768aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-4973000000-8df05b8993d29ece54f3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03fr-1090050000-e1da6480a9fd06afb04cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05di-3091000000-ec4150276195769266afView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-2290000000-5b3464d3f586e807998fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-63b925f61a9839949af2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001s-0088090000-3004385e526b292dd585View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001r-0088090000-f66d02576d7fdf24e8c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-3068c5d92f9bbd76997bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-3068c5d92f9bbd76997bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-e2bc2809b0d1b01fb842View 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 IDHMDB0007045
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024239
KNApSAcK IDNot Available
Chemspider ID24765879
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477980
PDB IDNot Available
ChEBI ID88782
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(14:1(9Z)/18:2(9Z,12Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/18:2(9Z,12Z))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(14:1(9Z)/18:2(9Z,12Z)/0:0) + Gamma-linolenoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/18:3(6Z,9Z,12Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Gondoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Docosanoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/22:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/18:2(9Z,12Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:2(9Z,12Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/18:2(9Z,12Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails