Showing metabocard for DG(16:1(9Z)/18:0/0:0) (BMDB0007129)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:31:10 UTC
Update Date2020-05-21 16:27:42 UTC
BMDB IDBMDB0007129
Secondary Accession Numbers
  • BMDB07129
Metabolite Identification
Common NameDG(16:1(9Z)/18:0/0:0)
DescriptionDG(16:1(9Z)/18:0/0:0), also known as DAG(16:1/18:0) or diacylglycerol(16:1/18:0), 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(16:1(9Z)/18:0/0:0) is considered to be a diradylglycerol lipid molecule. DG(16:1(9Z)/18:0/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(16:1(9Z)/18:0/0:0) exists in all living organisms, ranging from bacteria to humans. DG(16:1(9Z)/18:0/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(16:1(9Z)/18:0/0:0) can be converted into cytidine monophosphate and PE(16:1(9Z)/18:0) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(16:1(9Z)/18:0/0:0) can be converted into cytidine monophosphate and PC(16:1(9Z)/18:0) through the action of the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(16:1(9Z)/18:0/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(16:1(9Z)/18:0) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z-Hexadecenoyl)-2-octadecanoyl-sn-glycerolHMDB
DAG(16:1/18:0)HMDB
DAG(16:1N7/18:0)HMDB
DAG(16:1W7/18:0)HMDB
DAG(34:1)HMDB
DG(16:1(9Z)/18:0/0:0)[iso2]HMDB
DG(16:1/18:0)HMDB
DG(16:1/18:0/0:0)HMDB
Diacylglycerol(16:1/18:0)HMDB
Diacylglycerol(16:1n7/18:0)HMDB
Diacylglycerol(16:1W7/18:0)HMDB
1-Palmitoleoyl-2-stearoyl-sn-glycerolHMDB
DiglycerideHMDB
DiacylglycerolHMDB
Diacylglycerol(34:1)HMDB
DG(34:1)HMDB
DG(16:1(9Z)/18:0/0:0)Lipid Annotator
Chemical FormulaC37H70O5
Average Molecular Weight594.9487
Monoisotopic Molecular Weight594.52232535
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl octadecanoate
Traditional Namediacylglycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCC)=C(/[H])CCCCCCCC(=O)OC[C@]([H])(CO)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C37H70O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h14,16,35,38H,3-13,15,17-34H2,1-2H3/b16-14-/t35-/m0/s1
InChI KeySPBROLJVHYTNGF-BSNNDZOISA-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
logP10.1ALOGPS
logP12.53ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity178.02 m³·mol⁻¹ChemAxon
Polarizability78.28 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, Positivesplash10-0f79-4494345000-59d35e253ea6b00ea4ecView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/18:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-225d2aaf58bce54f763bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0009030000-f183eedacf0f1ac330a8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0009013000-57deb298c9560b801203View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-d1dcc3e98924441c6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0000009000-d1dcc3e98924441c6a0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03f0-0009000000-7ca12f4dfb6891cae0b4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001l-2095040000-a0947cdadda9ad358b37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-3095010000-90b367865c09b1402fbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-2490000000-3dcc4a70709fc9ed3c70View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000009000-665e2e7dfdb7932c6210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-0009030000-7c66433d593376a51f54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-0009013000-588ae60aeed8599a60a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02bg-2149050000-7e9b002b3f36098f0e10View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kf-5796010000-531b5343b33cfb43fde4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05ne-9200000000-5d5406d572a38ba6c011View 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 IDHMDB0007129
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 Compound9543691
PDB IDNot Available
ChEBI ID84418
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)/18:0/0:0) → Cytidine monophosphate + PE(16:1(9Z)/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(16:1(9Z)/18:0/0:0) + Stearoyl-CoA → TG(16:1(9Z)/18:0/18:0) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Oleoyl-CoA → TG(16:1(9Z)/18:0/18:1(9Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Gamma-linolenoyl-CoA → TG(16:1(9Z)/18:0/18:3(6Z,9Z,12Z))[iso6] + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Eicosanoyl-CoA → TG(16:1(9Z)/18:0/20:0) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Gondoyl-CoA → TG(16:1(9Z)/18:0/20:1(11Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + 5Z,8Z,11Z,14Z-eicosatetraenonyl-CoA → TG(16:1(9Z)/18:0/20:4(5Z,8Z,11Z,14Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Erucoyl-CoA → TG(16:1(9Z)/18:0/22:1(13Z)) + Coenzyme Adetails
DG(16:1(9Z)/18:0/0:0) + Clupanodonyl CoA → TG(16:1(9Z)/18:0/22:5(7Z,10Z,13Z,16Z,19Z))[iso6] + Coenzyme Adetails