Showing metabocard for DG(16:1(9Z)/22:1(13Z)/0:0) (BMDB0007145)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:29 UTC
Update Date2020-05-21 16:27:45 UTC
BMDB IDBMDB0007145
Secondary Accession Numbers
  • BMDB07145
Metabolite Identification
Common NameDG(16:1(9Z)/22:1(13Z)/0:0)
DescriptionDG(16:1(9Z)/22:1(13Z)/0:0)[iso2], also known as DAG(16:1/22:1) or dg(16:1(9z)/22:1(13z)/0:0)[iso2], belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/22:1(13z)/0:0)[iso2]s. These are dg(16:1(9z)/22:1(13z)/0:0)[iso2]s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/22:1(13Z)/0:0)[iso2] is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/22:1(13Z)/0:0)[iso2] is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. In cattle, DG(16:1(9Z)/22:1(13Z)/0:0)[iso2] is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/22:1(13Z)/22:2(13Z,16Z)) pathway and de novo triacylglycerol biosynthesis TG(16:1(9Z)/22:1(13Z)/22:5(4Z,7Z,10Z,13Z,16Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(38:2)HMDB
DAG(16:1/22:1)HMDB
Diacylglycerol(38:2)HMDB
Diacylglycerol(16:1/22:1)HMDB
DiglycerideHMDB
DG(38:2)HMDB
DiacylglycerolHMDB
DG(16:1/22:1)HMDB
1-Palmitoleoyl-2-erucoyl-sn-glycerolHMDB
1-(9Z-Hexadecenoyl)-2-(13Z-docosenoyl)-sn-glycerolHMDB
DG(16:1(9Z)/22:1(13Z)/0:0)Lipid Annotator
Chemical FormulaC41H76O5
Average Molecular Weight649.0391
Monoisotopic Molecular Weight648.569275542
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (13Z)-docos-13-enoate
Traditional Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (13Z)-docos-13-enoate
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H76O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h14,16-18,39,42H,3-13,15,19-38H2,1-2H3/b16-14-,18-17-/t39-/m0/s1
InChI KeyBRTWZKUDSRQGQH-NFIJARSKSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • 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
  • 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
logP10.47ALOGPS
logP13.95ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity197.54 m³·mol⁻¹ChemAxon
Polarizability85.03 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 (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/22:1(13Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-9cb3686d663a4e72a34aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0009004000-fcc9ca35a4e0bb19350eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0292-0009004000-afe26d341aef3249b226View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-2209016000-580b83674d5467fcd926View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-3219000000-2c3ba911fe6e902ec9b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-9817000000-ac6e56eb35963242b2bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-faa4fc25642155575980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000009000-faa4fc25642155575980View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0160-0019701000-01ab72d8c725b27227aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-93512236614722647238View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0009004000-a305824d5d3dc66c98a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0292-0009004000-ab2a224e1650b941f81bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1048009000-b25a910a79b98dc82dd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uki-4089001000-a578f8d28ba4c35f254bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-3596000000-410d44bf0d9b57e910c0View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • 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 IDHMDB0007145
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024339
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543780
PDB IDNot Available
ChEBI ID88483
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)/22:1(13Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/22:1(13Z))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)/22:1(13Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/22:1(13Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/22:1(13Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/22:1(13Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails