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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-09-12 01:12:42 UTC
Update Date2021-09-14 15:17:26 UTC
HMDB IDHMDB0006992
Secondary Accession Numbers
  • HMDB06992
Metabolite Identification
Common NameCDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z))
DescriptionCDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the eicsoatetraenoic acid moiety is derived from fish oils. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05% or so of the total phospholipids.
Structure
Data?1582752418
Synonyms
ValueSource
1-(11Z-Octadecenoyl)-2-(8Z,11Z,14Z,17Z-eicosapentaenoyl)-sn-glycero-3-CDPHMDB
1-Vaccenoyl-2-eicsoateHMDB
1-Vaccenoyl-2-eicsoatetraenoyl-sn-glycero-3-cytidine-5'-diphosphateHMDB
1-Vaccenoyl-2-eicsoic acidHMDB
CDP-DG(18:1/20:4)HMDB
CDP-DG(18:1N7/20:4N3)HMDB
CDP-DG(18:1W7/20:4W3)HMDB
CDP-DG(38:5)HMDB
CDP-Diacylglycerol(18:1/20:4)HMDB
CDP-Diacylglycerol(18:1N7/20:4N3)HMDB
CDP-Diacylglycerol(18:1W7/20:4W3)HMDB
CDP-Diacylglycerol(38:5)HMDB
Chemical FormulaC50H83N3O15P2
Average Molecular Weight1028.1526
Monoisotopic Molecular Weight1027.529942025
IUPAC Name[({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid
Traditional Name{[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC
InChI Identifier
InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h5,7,11,13-14,16-17,19,22,24,37-38,42-43,47-49,56-57H,3-4,6,8-10,12,15,18,20-21,23,25-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b7-5-,13-11-,16-14-,19-17-,24-22-/t42-,43-,47+,48?,49-/m1/s1
InChI KeyPOTUYISZWXOXIP-XOHYLDBDSA-N
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 DescriptorsNot Available
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
logP10(7.03) g/LALOGPS
logP10(10.14) g/LChemAxon
logS10(-5.8) g/LALOGPS
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 Count43ChemAxon
Refractivity273.4 m³·mol⁻¹ChemAxon
Polarizability111.54 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Positive-QTOFsplash10-03di-1920000100-a4552193682145f9aa952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Positive-QTOFsplash10-03di-2920000100-6567df9641d146e497e12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Positive-QTOFsplash10-03di-3931000000-14abd0b779afc4b8ac6c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Negative-QTOFsplash10-08gi-2892000302-18251a66071b9b3f66552017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Negative-QTOFsplash10-01q9-6692110200-1585be903f75cd23fcb92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Negative-QTOFsplash10-0bvi-5911000000-b524d099d78c3c5865872017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Negative-QTOFsplash10-004i-9000000200-2e4670a18f48522a05632021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Negative-QTOFsplash10-01r6-8091800300-f4b24ad58d1d38e6a5b52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Negative-QTOFsplash10-0a4i-9226300200-00aedb7bed917b6e29822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 10V, Positive-QTOFsplash10-004i-9000000006-944897ee260ae6dcb1f52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 20V, Positive-QTOFsplash10-0gw3-2000000019-d09b4b3b5cb708317c552021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - CDP-DG(18:1(11Z)/20:4(8Z,11Z,14Z,17Z)) 40V, Positive-QTOFsplash10-00du-0389841005-ed4dd0ed5d0bd6e43b0f2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB024186
KNApSAcK IDNot Available
Chemspider ID24765832
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477935
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Provides CDP-diacylglycerol an important precursor for the synthesis of phosphatidylinositol, phosphatidylglycerol, and cardiolipin.
Gene Name:
CDS2
Uniprot ID:
O95674
Molecular weight:
51417.5
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Provides CDP-diacylglycerol an important precursor for the synthesis of phosphatidylinositol (PtdIns), phosphatidylglycerol, and cardiolipin. Overexpression may amplify cellular signaling responses from cytokines. May also play an important role in the signal transduction mechanism of retina and neural cells.
Gene Name:
CDS1
Uniprot ID:
Q92903
Molecular weight:
53303.57
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due to the reverse reaction of PtdIns synthase and is dependent on CMP, which is tightly bound to the enzyme.
Gene Name:
CDIPT
Uniprot ID:
O14735
Molecular weight:
23538.47
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Functions in the biosynthesis of the anionic phospholipids phosphatidylglycerol and cardiolipin (By similarity).
Gene Name:
PGS1
Uniprot ID:
Q32NB8
Molecular weight:
62729.745