Showing metabocard for DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) (BMDB0007170)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:58 UTC
Update Date2020-05-21 16:27:47 UTC
BMDB IDBMDB0007170
Secondary Accession Numbers
  • BMDB07170
Metabolite Identification
Common NameDG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)
DescriptionDG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0), also known as DAG(18:0/20:4) or Dg(18:0/20:4(5z,8z,11z,14z)/0:0), 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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PE(18:0/20:4(5Z,8Z,11Z,14Z)) through the action of the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) can be converted into cytidine monophosphate and PC(18:0/20:4(5Z,8Z,11Z,14Z)); which is catalyzed by the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:0/20:4(5Z,8Z,11Z,14Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoateHMDB
1-Octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerolHMDB
1-Stearoyl-2-arachidonoylglycerolHMDB
DAG(18:0/20:4)HMDB
DAG(18:0/20:4OMEGA6)HMDB
DAG(38:4)HMDB
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2]HMDB
DG(18:0/20:4(OMEGA-6)/0:0)HMDB
DG(18:0/20:4)HMDB
DG(18:0/20:4/0:0)[iso2]HMDB
DG(18:0/20:4OMEGA6)HMDB
DG(38:4)HMDB
Diacylglycerol(18:0/20:4)HMDB
Diacylglycerol(18:0/20:4omega6)HMDB
Diacylglycerol(38:4)HMDB
(2S)-1-Hydroxy-3-(stearoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoic acidHMDB
1-Stearoyl-2-arachidonoyl-sn-glycerolHMDB
DAG(18:0/20:4N6)HMDB
DAG(18:0/20:4W6)HMDB
DG(18:0/20:4N6)HMDB
DG(18:0/20:4W6)HMDB
DiacylglycerolHMDB
Diacylglycerol(18:0/20:4n6)HMDB
Diacylglycerol(18:0/20:4W6)HMDB
DiglycerideHMDB
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)Lipid Annotator
Chemical FormulaC41H72O5
Average Molecular Weight645.0074
Monoisotopic Molecular Weight644.537975414
IUPAC Name(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional Namediacylglycerol
CAS Registry Number65914-84-3
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-/t39-/m0/s1
InChI KeyNSXLMTYRMFVYNT-IUJDHQGTSA-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
logP10.18ALOGPS
logP13.22ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity199.77 m³·mol⁻¹ChemAxon
Polarizability82.73 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, Positivesplash10-000i-2094021000-dc4f25c7f6771740e4a4View in MoNA
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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-07dw-1098005000-54d8ea3a74a349096badView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-1094011000-52b91d704579d19900e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-1092020000-75497a6666087c891081View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0fsu-0095003000-66d6ab68a36724fba8e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00lr-1093000000-b4d84c96409950a50516View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f8i-3093000000-4467873b87a3b64e5239View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1035009000-d647af2eb48b8222e6dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3093000000-29b342d9103a6ef93413View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kur-4094000000-24a375b31eb2c14b0849View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01rj-2097037000-bdd27099b40f8cb7a319View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-5296021000-efb2e651740275b40511View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g0-5389000000-8a039b037073454ffa2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-801cc9a5b0cfe9270f30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0009004000-16cae742717c466af29aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0009004000-56216388f2122cc39b7aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-610d69bd413f2e15b4e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-610d69bd413f2e15b4e0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03f0-0009000000-c2d933ac90e02d906dfaView 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 IDHMDB0007170
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024364
KNApSAcK IDNot Available
Chemspider ID4943054
KEGG Compound IDC00165
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438587
PDB IDNot Available
ChEBI ID75728
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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) → Cytidine monophosphate + PE(18:0/20:4(5Z,8Z,11Z,14Z))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(18:0/20:4(5Z,8Z,11Z,14Z)/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(18:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails