1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) (ECMDB21106) (M2MDB001515)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)XML
Proteins (3)
Record Information
Version2.0
Creation Date2012-07-30 14:54:38 -0600
Update Date2015-06-03 17:20:38 -0600
Secondary Accession Numbers
  • ECMDB21106
Identification
Name:1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1)
Description1,2-diacyl-sn-glycerol (dioctadec-11-enoyl, n-c18:1) 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)-3-hydroxy-2-(Z)-octadec-11-enoyloxypropyl (Z)-octadec-11-enoate
  • (2S)-3-Hydroxy-2-(Z)-octadec-11-enoyloxypropyl (Z)-octadec-11-enoic acid
  • 1,2-divaccenoyl-rac-glycerol
  • DAG(18:1/18:1)
  • DAG(18:1n7/18:1n7)
  • DAG(18:1w7/18:1w7)
  • DAG(36:2)
  • DG(18:1/18:1)
  • DG(18:1n7/18:1n7)
  • DG(18:1w7/18:1w7)
  • DG(36:2)
  • Diacylglycerol
  • Diacylglycerol(18:1/18:1)
  • Diacylglycerol(18:1n7/18:1n7)
  • Diacylglycerol(18:1w7/18:1w7)
  • Diacylglycerol(36:2)
  • Diglyceride
Chemical Formula:C39H72O5
Weight:Average: 620.986
Monoisotopic: 620.537975414
InChI Key:JQTCHIYVEDEVBR-ZHDGQSQGSA-N
InChI:InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13-16,37,40H,3-12,17-36H2,1-2H3/b15-13-,16-14-/t37-/m0/s1
CAS number:Not Available
IUPAC Name:(2S)-1-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propan-2-yl (11Z)-octadec-11-enoate
Traditional IUPAC Name:1,2-divaccenoyl-rac-glycerol
SMILES:[H][C@](CO)(COC(=O)CCCCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCC\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 DescriptorsNot Available
Physical Properties
State:Not Available
Charge:0
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.3e-05 g/LALOGPS
logP10.25ALOGPS
logP13.06ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability80.54 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 (dioctadec-11-enoyl, n-C18:1) + Phosphate
KDO2-Lipid A + PE(14:0/14:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphoethanolamine KDO(2)-lipid (A)
1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
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, Positivesplash10-03ki-4351957000-d2f6aa2881d4087272c2View 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(18:1(11Z)/18:1(11Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-9185b686832caa4f55c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0009009000-33724f4f211af0262245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009009000-36758b4e03b2a3c426eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-4045119000-5e45b0ab4ef272ef3017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014r-3095002000-9f50ccd5e21990627277View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-9487000000-4b085eb828d2b6eb9855View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0043009000-9ac33d92f73df92d1cb6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0089-3096001000-2a5cdd807461ff67255cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1190000000-76711955db6bcd2225ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0000009000-84cf426a5bd9b351e99aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0000009000-84cf426a5bd9b351e99aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0009001000-d276819fc45c2d6ea55eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-203520884a3c62e5734fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0008009000-5753add7ff34717540a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0008009000-e1ebc855e6b3195adfd9View in MoNA
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 ID88366
HMDB IDHMDB07188
Pubchem Compound ID53478063
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. 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
3. 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