DG(18:1(9Z)/18:1(9Z)/0:0) (ECMDB23311) (M2MDB003701)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-10-10 13:28:20 -0600
Update Date2015-12-09 14:10:46 -0700
Secondary Accession Numbers
  • ECMDB23311
Identification
Name:DG(18:1(9Z)/18:1(9Z)/0:0)
DescriptionDG(18:1(9Z)/18:1(9Z)/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(18:1(9Z)/18:1(9Z)/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1,2-di(9Z-octadecenoyl)-rac-glycerol
  • 1,2-Diolein
  • 1,2-dioleoyl-rac-glycerol
  • 3-hydroxy-2-(Z)-octadec-9-enoyloxypropyl (Z)-octadec-9-enoate
  • 3-Hydroxy-2-(Z)-octadec-9-enoyloxypropyl (Z)-octadec-9-enoic acid
  • 9-Octadecenoate (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester
  • 9-octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl ester
  • DAG(18:1/18:1)
  • DAG(36:2)
  • DG(18:1/18:1)
  • DG(36:2)
  • Diacylglycerol
  • Diacylglycerol(18:1/18:1)
  • Diacylglycerol(36:2)
  • Diglyceride
  • GLYCEROL DIOLEATE
  • GLYCEROL dioleic acid
Chemical Formula:C39H72O5
Weight:Average: 620.986
Monoisotopic: 620.537975414
InChI Key:DRAWQKGUORNASA-CLFAGFIQSA-N
InChI:InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-35-37(40)36-44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-
CAS number:Not Available
IUPAC Name:2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl (9Z)-octadec-9-enoate
Traditional IUPAC Name:2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propyl (9Z)-octadec-9-enoate
SMILES:CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COC(=O)CCCCCCC\C=C/CCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 3.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,3-diacylglycerols
Alternative Parents
Substituents
  • 1,3-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.2e-05 g/LALOGPS
logP10.28ALOGPS
logP13.06ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)13.63ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability81.4 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
LPA(18:1(9Z)/0:0) + Stearoyl-CoA + Stearoyl-CoA > Coenzyme A + DG(18:1(9Z)/18:1(9Z)/0:0) + DG(18:1(9Z)/18:1(9Z)/0:0)
LPA(18:1(9Z)/0:0) + acyl-[acp] > a holo-[acyl-carrier protein]  + DG(18:1(9Z)/18:1(9Z)/0:0) + DG(18:1(9Z)/18:1(9Z)/0:0)
DG(18:1(9Z)/18:1(9Z)/0:0) + Hydrogen ion + Cytidine triphosphate + DG(18:1(9Z)/18:1(9Z)/0:0) > Pyrophosphate + CDP-DG(18:1(9Z)/18:0) + CDP-DG(18:1(9Z)/18:0)
SMPDB Pathways:
phospholipid biosynthesis (CL(18:1/18:1/18:1/18:1))PW001027 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00tr-9351102000-e3d6976a4eb65131936fView 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(18:1n9/0:0/18:1n9),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1046009000-49c32aef4a0fca79c16cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02mr-3079002000-56f631186d8b17f3cbc9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2092000000-2aaab2f3f640e2baac09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-2057229000-d19de0ed9adc16ccea02View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05tr-5359232000-bd0cd90772f66480e4f9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-7449100000-daa8d4c560dcdb9923edView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID75735
HMDB IDHMDB0056197
Pubchem Compound ID5497165
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Phosphatidylglycerophosphatase B
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:
pgpB
Uniprot ID:
P0A924
Molecular weight:
29021
Reactions
Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.
Protein Details
2. Phosphatidate cytidylyltransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
CTP + phosphatidate = diphosphate + CDP- diacylglycerol
Gene Name:
cdsA
Uniprot ID:
P0ABG1
Molecular weight:
31453
Reactions
CTP + phosphatidate = diphosphate + CDP-diacylglycerol.
Protein Details
3. Diacylglycerol kinase
General function:
Involved in diacylglycerol kinase activity
Specific function:
Recycling of diacylglycerol produced during the turnover of membrane phospholipid
Gene Name:
dgkA
Uniprot ID:
P0ABN1
Molecular weight:
13245
Reactions
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate.
Protein Details
4. 1-acyl-sn-glycerol-3-phosphate acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsC
Uniprot ID:
P26647
Molecular weight:
27453
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1,2-diacyl-sn-glycerol 3-phosphate.