Showing metabocard for DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) (BMDB0007139)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:21 UTC
Update Date2020-05-21 16:27:44 UTC
BMDB IDBMDB0007139
Secondary Accession Numbers
  • BMDB07139
Metabolite Identification
Common NameDG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0)
DescriptionDG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0), also known as DG(16:1/20:3) or dg(16:1(9z)/20:3(5z,8z,11z)/0:0), belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/20:3(5z,8z,11z)/0:0)s. These are dg(16:1(9z)/20:3(5z,8z,11z)/0:0)s containing a glycerol acylated at positions 1 and 2. DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:3(5Z,8Z,11Z)); which is catalyzed by the enzyme phosphatidate phosphatase. Furthermore, DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) and docosanoyl-CoA can be converted into TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0) through the action of the enzyme dg(16:1(9z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. Furthermore, DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) can be biosynthesized from PA(16:1(9Z)/20:3(5Z,8Z,11Z)) through its interaction with the enzyme phosphatidate phosphatase. Finally, DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) and clupanodonoyl-CoA can be converted into TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) through its interaction with the enzyme dg(16:1(9z)/20:3(5z,8z,11z)/0:0) O-acyltransferase. In cattle, DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) is involved in a couple of metabolic pathways, which include de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:0) pathway and de novo triacylglycerol biosynthesis TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
DG(16:1/20:3)Lipid Annotator, HMDB
DG(36:4)Lipid Annotator, HMDB
DiglycerideLipid Annotator, HMDB
Diacylglycerol(36:4)Lipid Annotator, HMDB
Diacylglycerol(16:1/20:3)Lipid Annotator, HMDB
1-palmitoleoyl-2-meadoyl-sn-glycerolLipid Annotator, HMDB
DiacylglycerolLipid Annotator, HMDB
DAG(36:4)Lipid Annotator, HMDB
DAG(16:1/20:3)Lipid Annotator, HMDB
1-(9Z-hexadecenoyl)-2-(5Z,8Z,11Z-eicosatrienoyl)-sn-glycerolLipid Annotator, HMDB
DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0)Lipid Annotator
Chemical FormulaC39H68O5
Average Molecular Weight616.9542
Monoisotopic Molecular Weight616.506675286
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (5Z,8Z,11Z)-icosa-5,8,11-trienoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h14,16-18,20,22,26,28,37,40H,3-13,15,19,21,23-25,27,29-36H2,1-2H3/b16-14-,18-17-,22-20-,28-26-/t37-/m0/s1
InChI KeyCBNSYBOKMMVHOI-DYBBEDMHSA-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 DescriptorsNot Available
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
logP9.84ALOGPS
logP12.33ChemAxon
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 Count34ChemAxon
Refractivity190.57 m³·mol⁻¹ChemAxon
Polarizability78.57 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, Positivesplash10-0080-3392135000-1c5264d4280d9c33b065View 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(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-0033c71a807b4af9c6ccView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009031000-39d03b8a4ba5aa68dd9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009003000-2c7605ad836992cd02feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000009000-7da2b68332eda96bc7ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009031000-47811ca4383d898d37cdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009003000-7bdc36d15cffca72df3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-2068009000-64b22d472e3f2b64c057View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zmr-4094000000-14a113daa541a45822f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pbi-4294000000-4a9c8ed9871e7d4d0fe7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014s-2586169000-14fd93ae1eb15564abe8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3293010000-a8e60b1a9061318ec687View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rj-7796000000-dc446d1de740cc6e93fbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-c5201b03fd289f8bd404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000009000-c5201b03fd289f8bd404View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0009000000-48d50847f5fafc17cb1fView 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 IDHMDB0007139
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID24765945
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53478040
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(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) → Cytidine monophosphate + PE(16:1(9Z)/20:3(5Z,8Z,11Z))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)/20:3(5Z,8Z,11Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/20:3(5Z,8Z,11Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) + Erucoyl-CoA → TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/20:3(5Z,8Z,11Z)/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/20:3(5Z,8Z,11Z)/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails