Showing metabocard for DG(18:0/18:0/0:0) (BMDB0007158)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:44 UTC
Update Date2020-05-21 16:27:45 UTC
BMDB IDBMDB0007158
Secondary Accession Numbers
  • BMDB07158
Metabolite Identification
Common NameDG(18:0/18:0/0:0)
DescriptionDG(18:0/18:0/0:0), also known as dg(18:0/18:0/0:0) or DAG(18:0/18:0), belongs to the class of organic compounds known as 1,2-dg(18:0/18:0/0:0)s. These are dg(18:0/18:0/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(18:0/18:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/18:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/18:0/0:0) exists in all living organisms, ranging from bacteria to humans. DG(18:0/18:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:0/18:0/0:0) can be converted into cytidine monophosphate and PE(18:0/18:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:0/18:0/0:0) can be converted into cytidine monophosphate and PC(18:0/18:0); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:0/18:0/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(S)-Glycerin-1,2-distearatHMDB
(2S)-1,2-Bis-O-stearylglycerolHMDB
(2S)-3-Hydroxypropane-1,2-diyl distearoateHMDB
(S)-(-)-1,2-Distearoyl-sn-glycerolHMDB
(S)-1,2-DioctadecanoylglycerolHMDB
(S)-1,2-DistearoylglycerolHMDB
(S)-2,3-Bis-stearoyloxy-propan-1-olHMDB
1,2-Di-O-stearoyl-sn-glycerolHMDB
1,2-Distearoyl-sn-glycerolHMDB
Diacyl glycerolHMDB
(2S)-3-Hydroxypropane-1,2-diyl distearoic acidHMDB
DAG(36:0)HMDB
DAG(18:0/18:0)HMDB
Diacylglycerol(36:0)HMDB
Diacylglycerol(18:0/18:0)HMDB
DiglycerideHMDB
DG(18:0/18:0)HMDB
1,2-Distearoyl-rac-glycerolHMDB
DiacylglycerolHMDB
1,2-Dioctadecanoyl-rac-glycerolHMDB
DG(36:0)HMDB
DG(18:0/18:0/0:0)Lipid Annotator
Chemical FormulaC39H76O5
Average Molecular Weight625.0177
Monoisotopic Molecular Weight624.569275542
IUPAC Name(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl octadecanoate
Traditional Namediacyl glycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H76O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37,40H,3-36H2,1-2H3/t37-/m0/s1
InChI KeyUHUSDOQQWJGJQS-QNGWXLTQSA-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
logP10.36ALOGPS
logP13.78ChemAxon
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 Count38ChemAxon
Refractivity186.1 m³·mol⁻¹ChemAxon
Polarizability83.2 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, Positivesplash10-03dr-5151956000-f3cfe411b34b1c221b64View 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(18:0/18:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0a4i-0000009000-8e2b49808d5e3ba8021bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, positivesplash10-0a4i-7440009000-7ae5fe88175fdeb6fb5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-0a5a-9310001000-85fce82520a3cc11397aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-0ac1-9100000000-a1f2263667fdc881e94cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-0ac1-9100000000-3d9ba6996495929e12f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-b7a4da88d31b5bcc2c45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0009009000-1ba3fc9d6773d912e0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0009009000-e19946aa33b3b6470f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r3-1049008000-49dcad482d1f6cdbdb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-3197102000-2f093b5f0a07bfed3cb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9373000000-93a030c229e94346a6e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-1054009000-050434164c58cd42a01aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2095001000-85b9d03fc704e33c4ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1091000000-17b8d9f52bf6076415d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-4f85695573a777cd0fb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0008009000-7bc5dee7fe55e1f72047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0008009000-0348034e2d9f82dbea4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-0c5603e78a419f79d9c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-0c5603e78a419f79d9c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009001000-1fc1ebe517eccab43dabView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
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 IDHMDB0007158
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024352
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543705
PDB IDNot Available
ChEBI ID41847
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(18:0/18:0/0:0) → Cytidine monophosphate + PE(18:0/18:0)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(18:0/18:0/0:0) + Stearoyl-CoA → TG(18:0/18:0/18:0) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Oleoyl-CoA → TG(18:0/18:0/18:1(9Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Gamma-linolenoyl-CoA → TG(18:0/18:0/18:3(6Z,9Z,12Z))[iso3] + Coenzyme Adetails
DG(18:0/18:0/0:0) + Eicosanoyl-CoA → TG(18:0/18:0/20:0)[iso3] + Coenzyme Adetails
DG(18:0/18:0/0:0) + Gondoyl-CoA → TG(18:0/18:0/20:1(11Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:0/18:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Docosanoyl-CoA → TG(18:0/18:0/22:0) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Erucoyl-CoA → TG(18:0/18:0/22:1(13Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Clupanodonyl CoA → TG(18:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
DG(18:0/18:0/0:0) + Tetracosanoyl-CoA → TG(18:0/18:0/24:0) + Coenzyme Adetails