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Showing metabocard for DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) (BMDB0007047)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:26 UTC
Update Date2020-05-21 16:27:27 UTC
BMDB IDBMDB0007047
Secondary Accession Numbers
  • BMDB07047
Metabolite Identification
Common NameDG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0)
DescriptionDG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2], also known as DG(14:1/18:3) or dg(14:1(9z)/18:3(9z,12z,15z)/0:0)[iso2], 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)/18:3(9Z,12Z,15Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway and de novo triacylglycerol biosynthesis TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:3(8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DiglycerideHMDB
DG(32:4)HMDB
DG(14:1/18:3)HMDB
DAG(14:1/18:3)HMDB
Diacylglycerol(32:4)HMDB
Diacylglycerol(14:1/18:3)HMDB
DAG(32:4)HMDB
DiacylglycerolHMDB
1-(9Z-Tetradecenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerolHMDB
1-Myristoleoyl-2-a-linolenoyl-sn-glycerolHMDB
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC35H60O5
Average Molecular Weight560.8479
Monoisotopic Molecular Weight560.44407503
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propan-2-yl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C35H60O5/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/h5,7,10-13,16-17,33,36H,3-4,6,8-9,14-15,18-32H2,1-2H3/b7-5-,12-10-,13-11-,17-16-/t33-/m0/s1
InChI KeyVMPFJVBUSSLDKJ-UKRSEQBJSA-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
logP8.74ALOGPS
logP10.56ChemAxon
logS-7.3ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count30ChemAxon
Refractivity172.17 m³·mol⁻¹ChemAxon
Polarizability70.13 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, Positivesplash10-001i-6963113000-7a0e53b458b35789b12fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(14:1(9Z)/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, Positivesplash10-004i-0000090000-5640aeb4d5a7f43d6aa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0023-0099090000-986e8e6ea01ab348bd6dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0049-0099090000-356bcf3c5c8e3f660992View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-1090050000-cf9271b8e5bd20d73141View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-3091000000-b25d9d9060a1b2211fddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3190000000-57d38a41eed3f1f5b37cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-23d1d3bce383e41915ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0000090000-23d1d3bce383e41915ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0009000000-feac721ba70aad353a0eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0343690000-4cad87dd6c1ca1bbdf42View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-2592010000-af816837f78fe9d280fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03mr-3964100000-b5e2ec17c9d6573afa0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0000090000-8b29ca4be3b11676db69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0023-0088090000-33d726ab2a7103e46a36View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0049-0088090000-9169b9b71bd676734b92View 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 IDHMDB0007047
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477982
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(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(14:1(9Z)/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(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Docosanoyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:0)[iso6] + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(14:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(14:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails