Showing metabocard for DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) (BMDB0007033)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:29:09 UTC
Update Date2020-05-21 16:27:24 UTC
BMDB IDBMDB0007033
Secondary Accession Numbers
  • BMDB07033
Metabolite Identification
Common NameDG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0)
DescriptionDG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0), also known as diacylglycerol(14:0/22:5) or DAG(14:0/22:5), belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) can be biosynthesized from PA(14:0/22:5(7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme phosphatidate phosphatase. In addition, DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) and docosahexaenoyl-CoA can be converted into TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)); which is catalyzed by the enzyme diacylglycerol O-acyltransferase. In cattle, DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DAG(36:5)Lipid Annotator, HMDB
1-myristoyl-2-docosapentaenoyl-sn-glycerolLipid Annotator, HMDB
DG(36:5)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
Diacylglycerol(14:0/22:5)Lipid Annotator, HMDB
DAG(14:0/22:5)Lipid Annotator, HMDB
Diacylglycerol(36:5)Lipid Annotator, HMDB
DG(14:0/22:5)Lipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
1-tetradecanoyl-2-(7Z,10Z,13Z,16Z,19Z-docosapentaenoyl)-sn-glycerolLipid Annotator, HMDB
DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0)Lipid Annotator
Chemical FormulaC39H66O5
Average Molecular Weight614.9383
Monoisotopic Molecular Weight614.491025222
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C39H66O5/c1-3-5-7-9-11-13-15-16-17-18-19-20-21-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-14-12-10-8-6-4-2/h5,7,11,13,16-17,19-20,22,24,37,40H,3-4,6,8-10,12,14-15,18,21,23,25-36H2,1-2H3/b7-5-,13-11-,17-16-,20-19-,24-22-/t37-/m0/s1
InChI KeyUNAUUXGPAPFTQK-MTCOIHPXSA-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
StatusDetected 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
logP9.31ALOGPS
logP11.97ChemAxon
logS-7.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count33ChemAxon
Refractivity191.69 m³·mol⁻¹ChemAxon
Polarizability76.69 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 (Non-derivatized) - 70eV, Positivesplash10-01qi-4795020000-5c424ce537568b270ef9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ei-7963304000-010cf221080784b4767aView in MoNA
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(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03y0-1198023000-13e0e123db226e9b4b4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-3497120000-c79869459ad1048a5562View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03y0-1693030000-f352cda3f2667d1acdbcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-06vi-0094002000-4c05751603b973626c2cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-1193000000-0124d82b8666245aba53View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4195000000-7cc4eec5c32ff25536b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02ti-1019144000-5f63b80d43e408488c6bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-1049010000-0610f37437eed9417ce0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dr-2349100000-24bc3f99d6b125404a3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-76503681101bfbcc5bcfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0099063000-2f2086e82a02d8ea16b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0099017000-afb6c5e3c431b46b8659View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1035009000-370c3a4d7bc2a704c714View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-3092000000-d1581ca7a067b151ebb9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-4395000000-dc15c2ca3f3250f3b0a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-c292a667c0eda7d86f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0019701000-945eec3279dace8d293eView in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen Locations
  • All Tissues
  • Milk
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007033
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765867
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477968
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tang C, Zhang K, Zhan T, Zhao Q, Zhang J: Metabolic Characterization of Dairy Cows Treated with Gossypol by Blood Biochemistry and Body Fluid Untargeted Metabolome Analyses. J Agric Food Chem. 2017 Oct 25;65(42):9369-9378. doi: 10.1021/acs.jafc.7b03544. Epub 2017 Oct 17. [PubMed:28965405 ]

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(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) → Cytidine monophosphate + PE(14:0/22:5(7Z,10Z,13Z,16Z,19Z))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(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) + Clupanodonyl CoA → TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/0:0) + Tetracosanoyl-CoA → TG(14:0/22:5(7Z,10Z,13Z,16Z,19Z)/24:0) + Coenzyme Adetails