Showing metabocard for DG(16:1(9Z)/22:0/0:0) (BMDB0007144)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:27 UTC
Update Date2020-05-21 16:29:06 UTC
BMDB IDBMDB0007144
Secondary Accession Numbers
  • BMDB07144
Metabolite Identification
Common NameDG(16:1(9Z)/22:0/0:0)
DescriptionDG(16:1(9Z)/22:0/0:0), also known as dg(16:1(9z)/22:0/0:0) or DG(16:1/22:0), belongs to the class of organic compounds known as 1,2-dg(16:1(9z)/22:0/0:0)s. These are dg(16:1(9z)/22:0/0:0)s containing a glycerol acylated at positions 1 and 2. Thus, DG(16:1(9Z)/22:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/22:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/22:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, DG(16:1(9Z)/22:0/0:0) can be biosynthesized from PA(16:1(9Z)/22:0) through the action of the enzyme phosphatidate phosphatase. In addition, DG(16:1(9Z)/22:0/0:0) and clupanodonoyl-CoA can be converted into TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)); which is mediated by the enzyme dg(16:1(9z)/22:0/0:0) O-acyltransferase. In cattle, DG(16:1(9Z)/22:0/0:0) is involved in the metabolic pathway called de novo triacylglycerol biosynthesis TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Diacylglycerol(38:1)HMDB
DAG(38:1)HMDB
DG(16:1/22:0)HMDB
Diacylglycerol(16:1/22:0)HMDB
DiglycerideHMDB
DiacylglycerolHMDB
1-Palmitoleoyl-2-behenoyl-sn-glycerolHMDB
DG(38:1)HMDB
1-(9Z-Hexadecenoyl)-2-docosanoyl-sn-glycerolHMDB
DAG(16:1/22:0)HMDB
DG(16:1(9Z)/22:0/0:0)Lipid Annotator
Chemical FormulaC41H78O5
Average Molecular Weight651.055
Monoisotopic Molecular Weight650.584925606
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl docosanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C41H78O5/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/h14,16,39,42H,3-13,15,17-38H2,1-2H3/b16-14-/t39-/m0/s1
InChI KeyBZRVDTDUKMXTCU-QZEPCWIRSA-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
logP10.53ALOGPS
logP14.31ChemAxon
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 Count39ChemAxon
Refractivity196.42 m³·mol⁻¹ChemAxon
Polarizability86.67 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)/22:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-41a111147518b48db160View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03eb-0009004000-12be9434944ee7f489ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xt-0009004000-96bf7963ded5f5659f4eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-9359ef56bc4c032da2a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03eb-0009004000-a8268024df9628b211dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xt-0009004000-14c41b13b9a25b3cf19fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-2119015000-bf85acdca377873438caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2119001000-1388112fbbaa461c89ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dj-9616000000-0e6bb77cd0a3d1d33bbbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1087009000-0b204f92747aaa73719cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fya-3059001000-766d97f3ee5507040c69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-3398000000-a9e9eaeba5ba2e0596dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0000009000-4127af242e0db0c15575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0000009000-4127af242e0db0c15575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0160-0019701000-857338159f8036ca8756View 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 IDHMDB0007144
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543771
PDB IDNot Available
ChEBI ID88484
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)/22:0/0:0) → Cytidine monophosphate + PE(16:1(9Z)/22:0)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(16:1(9Z)/22:0/0:0) + Erucoyl-CoA → TG(16:1(9Z)/22:0/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/22:0/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/22:0/22:5(7Z,10Z,13Z,16Z,19Z)) + Coenzyme Adetails
Enzyme Details
3. Patatin-like phospholipase domain-containing protein 2
General function:
Not Available
Specific function:
Catalyzes the initial step in triglyceride hydrolysis in adipocyte and non-adipocyte lipid droplets. Also has acylglycerol transacylase activity. May act coordinately with LIPE/HLS within the lipolytic cascade. Regulates adiposome size and may be involved in the degradation of adiposomes. May play an important role in energy homeostasis. May play a role in the response of the organism to starvation, enhancing hydrolysis of triglycerides and providing free fatty acids to other tissues to be oxidized in situations of energy depletion.
Gene Name:
PNPLA2
Uniprot ID:
Q2KI18
Molecular weight:
53417.0
Reactions
Retinyl ester + DG(16:1(9Z)/22:0/0:0) → Vitamin A + TG(16:1(9Z)/22:0/16:1(9Z))details