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Record Information
Version4.0
Creation Date2008-09-12 01:12:40 UTC
Update Date2017-09-27 08:24:50 UTC
HMDB IDHMDB0006990
Secondary Accession Numbers
  • HMDB06990
Metabolite Identification
Common NameCDP-DG(18:1(11Z)/18:2(9Z,12Z))
DescriptionCDP-DG(18:1(11Z)/18:2(9Z,12Z)) 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)/18:2(9Z,12Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the linoleic acid moiety is derived from seed 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
Thumb
Synonyms
ValueSource
1-(11Z-Octadecenoyl)-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-CDPHMDB
1-Vaccenoyl-2-linoleoyl-sn-glycero-3-cytidine-5'-diphosphateHMDB
CDP-DG(18:1/18:2)HMDB
CDP-DG(18:1N7/18:2N6)HMDB
CDP-DG(18:1W7/18:2W6)HMDB
CDP-DG(36:3)HMDB
CDP-Diacylglycerol(18:1/18:2)HMDB
CDP-Diacylglycerol(18:1N7/18:2N6)HMDB
CDP-Diacylglycerol(18:1W7/18:2W6)HMDB
CDP-Diacylglycerol(36:3)HMDB
Chemical FormulaC48H83N3O15P2
Average Molecular Weight1004.1312
Monoisotopic Molecular Weight1003.529942025
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)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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)-3-[(11Z)-octadec-11-enoyloxy]-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]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)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C48H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-43(52)61-37-40(64-44(53)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2)38-62-67(57,58)66-68(59,60)63-39-41-45(54)46(55)47(65-41)51-36-35-42(49)50-48(51)56/h12-15,18,20,35-36,40-41,45-47,54-55H,3-11,16-17,19,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b14-12-,15-13-,20-18-/t40-,41-,45+,46?,47-/m1/s1
InChI KeyYGZYGQXACNZDAJ-KVGNFNSDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerophospholipids
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
  • Alkyl phosphate
  • Pyrimidine
  • Fatty acyl
  • Primary aromatic amine
  • Dicarboxylic acid or derivatives
  • Phosphoric acid ester
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Heteroaromatic compound
  • Oxolane
  • Amino acid or derivatives
  • Secondary alcohol
  • 1,2-diol
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Alcohol
  • Primary amine
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological Location:

  Subcellular:

  Tissue and substructures:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Role

Biological role:

Industrial application:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0032 g/LALOGPS
logP6.86ALOGPS
logP9.97ChemAxon
logS-5.5ALOGPS
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
Refractivity261.96 m³·mol⁻¹ChemAxon
Polarizability108.35 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0910000100-710a97ec93ca19072aa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910001100-40fd51731398748c9119View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3921000100-7e05c66a52bfc52ae354View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-08gi-2890000402-fdfea0a5d2dbfda432b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03e9-5692300301-bcfd475e84016be6294bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-5921000000-8e30159e6076110614d9View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
Cardiolipin Biosynthesis CL(16:0/16:0/18:1(11Z)/18:2(9Z,12Z))Pw027866Pw027866 greyscalePw027866 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:1(11Z)/18:2(9Z,12Z))Pw028045Pw028045 greyscalePw028045 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:1(11Z)/18:2(9Z,12Z))Pw028101Pw028101 greyscalePw028101 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:1(11Z)/18:2(9Z,12Z))Pw028152Pw028152 greyscalePw028152 simpleNot Available
Cardiolipin Biosynthesis CL(16:1(9Z)/16:1(9Z)/18:1(11Z)/18:2(9Z,12Z))Pw028415Pw028415 greyscalePw028415 simpleNot Available
Displaying entries 1 - 5 of 60 in total
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024184
KNApSAcK IDNot Available
Chemspider ID24765830
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477933
PDB IDNot Available
ChEBI 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