CDP-1,2-dihexadecanoylglycerol (ECMDB21189) (M2MDB001598)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (4)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-07-30 14:54:48 -0600
Update Date2015-06-03 17:20:50 -0600
Secondary Accession Numbers
  • ECMDB21189
Identification
Name:CDP-1,2-dihexadecanoylglycerol
DescriptionCdp-1,2-dihexadecanoylglycerol belongs to the class of CDP-Diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 1,2-Dihexadecanoyl-sn-glycero-3-CDP
  • 1,2-Dihexadecanoyl-sn-glycero-3-cytidine 5'-diphosphate
  • 1,2-Dihexadecanoyl-sn-glycero-3-cytidine 5'-diphosphoric acid
  • 1,2-Dipalmitoyl-sn-glycero-3-CDP
  • 1,2-Dipalmitoyl-sn-glycero-3-cytidine 5'-diphosphate
  • 1,2-Dipalmitoyl-sn-glycero-3-cytidine 5'-diphosphoric acid
  • CDP-1,2-Dipalmitoylglycerol
  • CDP-DG(16:0/16:0)
  • CDP-DG(32:0)
  • CDP-Diacylglycerol(16:0/16:0)
  • CDP-Diacylglycerol(32:0)
  • CDP-Dihexadecanoyl-sn-glycerol
Chemical Formula:C44H81N3O15P2
Weight:Average: 954.0726
Monoisotopic: 953.514291961
InChI Key:ITYHVANGBZMQML-BQUKFSKHSA-N
InChI:InChI=1S/C44H81N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-39(48)57-33-36(60-40(49)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)34-58-63(53,54)62-64(55,56)59-35-37-41(50)42(51)43(61-37)47-32-31-38(45)46-44(47)52/h31-32,36-37,41-43,50-51H,3-30,33-35H2,1-2H3,(H,53,54)(H,55,56)(H2,45,46,52)/t36-,37-,41-,42-,43-/m1/s1
CAS number:Not Available
IUPAC Name:[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphinic acid
Traditional IUPAC Name:{[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2,3-bis(hexadecanoyloxy)propoxyphosphinic acid
SMILES:CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as cdp-diacylglycerols. These are glycerolipids containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassCDP-glycerols
Direct ParentCDP-diacylglycerols
Alternative Parents
Substituents
  • Cdp-diacylglycerol
  • Pyrimidine ribonucleoside diphosphate
  • Diacyl-glycerol-3-pyrophosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Aminopyrimidine
  • Fatty acid ester
  • Pyrimidone
  • Monoalkyl phosphate
  • Imidolactam
  • Pyrimidine
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Dicarboxylic acid or derivatives
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Secondary alcohol
  • Amino acid or derivatives
  • 1,2-diol
  • Carboxylic acid ester
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Alcohol
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Amine
  • Carbonyl group
  • Primary amine
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP5.98ALOGPS
logP9.28ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area263.27 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity240.21 m³·mol⁻¹ChemAxon
Polarizability104.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadecanoylglycerol + Pyrophosphate
CDP-1,2-dihexadecanoylglycerol + Glycerol 3-phosphate > Cytidine monophosphate + Hydrogen ion + PGP(16:0/16:0)
CDP-1,2-dihexadecanoylglycerol + L-Serine > Cytidine monophosphate + Hydrogen ion + PS(16:0/16:0)
CDP-1,2-dihexadecanoylglycerol + Water > Cytidine monophosphate +2 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 LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910001001-c6c82ba3914b2ced1f41View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910001000-b21fc6ff065a0ee9b608View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-2920010000-0aec2f1c5b74c03c42f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0980002204-ef53ba06ec0de8aaed7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-4792300201-2d6f40a75ba121c0c3d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5921000000-742a306835ddae8d70e0View in MoNA
MSMass Spectrum (Electron Ionization)Not 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
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 ID77358
HMDB IDNot Available
Pubchem Compound ID45934309
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. CDP-diacylglycerol pyrophosphatase
General function:
Involved in CDP-diacylglycerol diphosphatase activity
Specific function:
CDP-diacylglycerol + H(2)O = CMP + phosphatidate
Gene Name:
cdh
Uniprot ID:
P06282
Molecular weight:
28451
Reactions
CDP-diacylglycerol + H(2)O = CMP + phosphatidate.
Protein Details
2. CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
This protein catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:
pgsA
Uniprot ID:
P0ABF8
Molecular weight:
20700
Reactions
CDP-diacylglycerol + sn-glycerol 3-phosphate = CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.
Protein Details
3. 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
4. CDP-diacylglycerol--serine O-phosphatidyltransferase
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
CDP-diacylglycerol + L-serine = CMP + (3-sn- phosphatidyl)-L-serine
Gene Name:
pssA
Uniprot ID:
P23830
Molecular weight:
52801
Reactions
CDP-diacylglycerol + L-serine = CMP + (3-sn-phosphatidyl)-L-serine.