1,2-Dioctadecanoyl-sn-glycerol (ECMDB21466) (M2MDB001861)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-08-09 09:25:03 -0600
Update Date2015-06-03 17:21:34 -0600
Secondary Accession Numbers
  • ECMDB21466
Identification
Name:1,2-Dioctadecanoyl-sn-glycerol
Description1,2-dioctadecanoyl-sn-glycerol is a member of the chemical class known as Diacylglycerols. These are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. 1,2-dioctadecanoyl-sn-glycerol is an intermediate in the synthesis of phopsholipids and glycerolipids with a pair of C18 chains.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • ()-(S)-Glycerin-1,2-distearat
  • (2S)-1,2-bis-O-stearylglycerol
  • (2S)-3-hydroxypropane-1,2-diyl dioctadecanoate
  • (2S)-3-hydroxypropane-1,2-diyl dioctadecanoic acid
  • (2S)-3-hydroxypropane-1,2-diyl distearoate
  • (2S)-3-hydroxypropane-1,2-diyl distearoic acid
  • (S)-()-1,2-distearoyl-sn-glycerol
  • (S)-1,2-distearoylglycerol
  • (S)-2,3-bis-stearoyloxy-propan-1-ol
  • 1,2-Di-O-stearoyl-sn-glycerol
  • 1,2-Dioctadecanoyl-sn-glycerol
  • 1,2-Distearoyl-sn-glycerol
  • DG(18:0/18:0/0:0)
  • DIACYL GLYCEROL
Chemical Formula:C39H76O5
Weight:Average: 625.0177
Monoisotopic: 624.569275542
InChI Key:UHUSDOQQWJGJQS-QNGWXLTQSA-N
InChI:InChI=1S/C39H76O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37,40H,3-36H2,1-2H3/t37-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl octadecanoate
Traditional IUPAC Name:diacyl glycerol
SMILES:[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
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 Solubility1.7e-05 g/LALOGPS
logP10.36ALOGPS
logP13.78ChemAxon
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 Count38ChemAxon
Refractivity186.1 m³·mol⁻¹ChemAxon
Polarizability83.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
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, Positivesplash10-03dr-5151956000-f3cfe411b34b1c221b64View 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(18:0/18:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0a4i-0000009000-8e2b49808d5e3ba8021bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, positivesplash10-0a4i-7440009000-7ae5fe88175fdeb6fb5fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-0a5a-9310001000-85fce82520a3cc11397aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 52V, positivesplash10-0ac1-9100000000-a1f2263667fdc881e94cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 59V, positivesplash10-0ac1-9100000000-3d9ba6996495929e12f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-b7a4da88d31b5bcc2c45View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0009009000-1ba3fc9d6773d912e0efView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0009009000-e19946aa33b3b6470f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05r3-1049008000-49dcad482d1f6cdbdb6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-066u-3197102000-2f093b5f0a07bfed3cb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0693-9373000000-93a030c229e94346a6e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00e9-1054009000-050434164c58cd42a01aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2095001000-85b9d03fc704e33c4ca1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00lr-1091000000-17b8d9f52bf6076415d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-4f85695573a777cd0fb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052f-0008009000-7bc5dee7fe55e1f72047View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0008009000-0348034e2d9f82dbea4aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0000009000-0c5603e78a419f79d9c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0000009000-0c5603e78a419f79d9c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009001000-1fc1ebe517eccab43dabView 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:
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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 ID41847
HMDB IDHMDB0007158
Pubchem Compound ID9543705
Kegg IDNot Available
ChemSpider ID7822655
Wikipedia IDNot Available
BioCyc IDNot Available
Ligand ExpoDGA

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. 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.