Showing metabocard for DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) (BMDB0007134)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:16 UTC
Update Date2020-05-21 16:27:43 UTC
BMDB IDBMDB0007134
Secondary Accession Numbers
  • BMDB07134
Metabolite Identification
Common NameDG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)
DescriptionDG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2], also known as dg(16:1(9z)/18:3(9z,12z,15z)/0:0)[iso2] or Dg(16:1(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(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)[iso2] is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:1(9Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Palmitoleoyl-2-a-linolenoyl-sn-glycerolHMDB
1-Palmitoleoyl-2-alpha-linolenoyl-sn-glycerolHMDB
DAG(16:1/18:3)HMDB
DAG(16:1N7/18:3N3)HMDB
DAG(16:1W7/18:3W3)HMDB
DAG(34:4)HMDB
DG(16:1/18:3)HMDB
DG(16:1N7/18:3N3)HMDB
DG(16:1W7/18:3W3)HMDB
DG(34:4)HMDB
DiacylglycerolHMDB
Diacylglycerol(16:1/18:3)HMDB
Diacylglycerol(16:1n7/18:3n3)HMDB
Diacylglycerol(16:1W7/18:3W3)HMDB
Diacylglycerol(34:4)HMDB
DiglycerideHMDB
1-(9Z-Hexadecenoyl)-2-(9Z,12Z,15Z-octadeatrienoyl)-sn-glycerolHMDB
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0)Lipid Annotator
Chemical FormulaC37H64O5
Average Molecular Weight588.9011
Monoisotopic Molecular Weight588.475375158
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-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/CCCCCC)OC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C37H64O5/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/h5,7,11,13-14,16-18,35,38H,3-4,6,8-10,12,15,19-34H2,1-2H3/b7-5-,13-11-,16-14-,18-17-/t35-/m0/s1
InChI KeyUUPFPLJLQPYEKS-BTMLKTQRSA-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
logP9.36ALOGPS
logP11.44ChemAxon
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 Count32ChemAxon
Refractivity181.37 m³·mol⁻¹ChemAxon
Polarizability74.26 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, Positivesplash10-01ws-6693104000-b2cfcecfe45ee1699092View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(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, Positivesplash10-0a4i-0000009000-b3b3c003f4a39cd41d77View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0009030000-70e6e4935063b5428267View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0009013000-a43739497c7c75e47e3fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f9i-2085090000-35890b891935e98b493aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmr-3092010000-3425107776fd6377b2d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zi9-3190000000-ae1f17173bd81ecd22b2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1342290000-60b881454bea5232591fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-3693010000-b5f77aca7dedd5cc42f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-5975000000-2c22f09c54bbb7227bbaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000009000-ef32778e747adcbc98abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01w0-0009030000-67a9c3f423e70b8b88f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06ri-0009013000-60bfd2c4ddb19425f811View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000009000-7aced06f5b39c28eb59fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a60-0009000000-60e148355d022c1b453bView 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 IDHMDB0007134
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024328
KNApSAcK IDNot Available
Chemspider ID7822653
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543703
PDB IDNot Available
ChEBI ID88497
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(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) → Cytidine monophosphate + PE(16:1(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(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:0)[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Gondoyl-CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:1(11Z))[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:3(9Z,12Z,15Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/18:3(9Z,12Z,15Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails