1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) (ECMDB21104) (M2MDB001513)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-07-30 14:54:38 -0600
Update Date2015-06-03 17:20:38 -0600
Secondary Accession Numbers
  • ECMDB21104
Identification
Name:1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1)
Description1,2-diacyl-sn-glycerol (dihexadec-9-enoyl, n-c16:1) belongs to the class of Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • (2S)-2-(Z)-hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoate
  • (2S)-2-(Z)-Hexadec-9-enoyloxy-3-hydroxypropyl (Z)-hexadec-9-enoic acid
Chemical Formula:C35H64O5
Weight:Average: 564.8797
Monoisotopic: 564.475375158
InChI Key:HSQHRRHRYJNSOC-DWCRPSDDSA-N
InChI:InChI=1S/C35H64O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,33,36H,3-12,17-32H2,1-2H3/b15-13-,16-14-/t33-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (9Z)-hexadec-9-enoate
Traditional IUPAC Name:diacylglycerol
SMILES:[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCC\C=C/CCCCCC
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
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.5e-05 g/LALOGPS
logP9.63ALOGPS
logP11.28ChemAxon
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 Count32ChemAxon
Refractivity169.93 m³·mol⁻¹ChemAxon
Polarizability72.16 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphate
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphoethanolamine KDO(2)-lipid (A)
1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
2 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Cytidine triphosphate + Hydrogen ion >2 CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate
SMPDB Pathways:
phospholipid biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z))PW001549 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, Positivesplash10-008i-4449464000-50b6a5cf704160fba39dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(16:1(9Z)/16:1(9Z)/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, Positivesplash10-001i-0000090000-51d305f10f90afe4eb07View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0009090000-367853de731f7e261d22View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0009090000-736308809e6d3cc751f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0043090000-9be462094b27393e9285View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0w2i-2092000000-a9d9a5b97c3b76b05af0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udr-1290000000-987ad4e1a1321117b546View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-2244390000-c5ba870493b35853231dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-7294120000-5fb9d214e1f99e650a8fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06rj-9363000000-500eddc99602756cec87View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0000090000-279f8e7a1315590373dcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dj-0008090000-54ee6ee0a058250d5412View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03e9-0008090000-cd2f6f1c784cfcb067d1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000090000-ec1b73afc18d0387d07fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-0019010000-2a8ef0425a75fbd6ee6cView 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 ID84417
HMDB IDHMDB0007128
Pubchem Compound ID9543679
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. Phosphoethanolamine transferase eptB
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphoethanolamine (pEtN) moiety to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A. Phosphatidylethanolamines with one unsaturated acyl group functions as pEtN donors and the reaction releases diacylglycerol
Gene Name:
eptB
Uniprot ID:
P37661
Molecular weight:
63804