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Record Information
Version4.0
Creation Date2008-09-12 01:12:22 UTC
Update Date2017-09-27 08:24:50 UTC
HMDB IDHMDB0006972
Secondary Accession Numbers
  • HMDB06972
Metabolite Identification
Common NameCDP-DG(16:0/18:2(9Z,12Z))
DescriptionCDP-DG(16:0/18:2(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(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, 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-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-CDPHMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-cytidine-5'-diphosphateHMDB
CDP-DG(16:0/18:2)HMDB
CDP-DG(16:0/18:2N6)HMDB
CDP-DG(16:0/18:2W6)HMDB
CDP-DG(34:2)HMDB
CDP-Diacylglycerol(16:0/18:2)HMDB
CDP-Diacylglycerol(16:0/18:2N6)HMDB
CDP-Diacylglycerol(16:0/18:2W6)HMDB
CDP-Diacylglycerol(34:2)HMDB
Chemical FormulaC46H81N3O15P2
Average Molecular Weight978.094
Monoisotopic Molecular Weight977.514291961
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-(hexadecanoyloxy)-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-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphinic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(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/C46H81N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-42(51)62-38(35-59-41(50)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h11,13,17-18,33-34,38-39,43-45,52-53H,3-10,12,14-16,19-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/b13-11-,18-17-/t38-,39-,43+,44?,45-/m1/s1
InChI KeySDCBTFIMVHXFSZ-GTSRJJEASA-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 Solubility0.0045 g/LALOGPS
logP6.52ALOGPS
logP9.45ChemAxon
logS-5.3ALOGPS
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
Refractivity251.65 m³·mol⁻¹ChemAxon
Polarizability106.46 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-0920000101-91c1f5aec13e2af5c5deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1920001000-b91b10282cde34849e52View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3930000000-9260f91debe32e0fe1b7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0bt9-0690001203-5278055288341344f6d5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-5692200201-1f946b602731fa72eaebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5921000000-1f07d63834de74cf0586View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:2(9Z,12Z))Pw027836Pw027836 greyscalePw027836 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/16:0/18:2(9Z,12Z))Pw027935Pw027935 greyscalePw027935 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:0/16:0/18:2(9Z,12Z))Pw027982Pw027982 greyscalePw027982 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/16:0/18:2(9Z,12Z))Pw028027Pw028027 greyscalePw028027 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/16:0/18:2(9Z,12Z))Pw028083Pw028083 greyscalePw028083 simpleNot Available
Displaying entries 1 - 5 of 48 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 IDFDB024166
KNApSAcK IDNot Available
Chemspider ID24765812
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477916
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