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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2008-09-12 01:12:18 UTC
Update Date2017-12-07 02:00:16 UTC
HMDB IDHMDB0006968
Secondary Accession Numbers
  • HMDB06968
Metabolite Identification
Common NameCDP-DG(16:0/16:0)
DescriptionCDP-DG(16:0/16:0) 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(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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
1,2-Dihexadecanoyl-rac-glycero-3-CDPHMDB
1,2-Dipalmitoyl-rac-glycero-3-cytidine-5'-diphosphateHMDB
CDP-DG(32:0)HMDB
CDP-Diacylglycerol(16:0/16:0)HMDB
CDP-Diacylglycerol(32:0)HMDB
Chemical FormulaC44H81N3O15P2
Average Molecular Weight954.086
Monoisotopic Molecular Weight953.514292916
IUPAC Name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2,3-bis(hexadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
Traditional Name[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2,3-bis(hexadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic 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)CCCCCCCCCCCCCCC
InChI Identifier
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
InChI KeyITYHVANGBZMQML-QDFYKRCGSA-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 Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Tissue and substructures:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Cellular process:

    Chemical reaction:

    Biochemical process:

Role

Biological role:

Industrial application:

  Food and nutrition:

Physiological effect

Organoleptic effect:

  Touch:

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 Solubility0.0058 g/LALOGPS
logP5.98ALOGPS
logP9.56ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area263.27 ŲChemAxon
Rotatable Bond Count42ChemAxon
Refractivity240.21 m³·mol⁻¹ChemAxon
Polarizability105.2 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-0910001001-c3de6e15431b5ac5105eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1910001000-94fe74d873da591ba587View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3920010100-8cfc73d1ce30a6c32997View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0980001205-1542b6ae52ff3efc590aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0bt9-5792301301-02cf7e042d4983495f65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bt9-5910000000-476fcc03a8d550c335c6View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:0)Pw027831Pw027831 greyscalePw027831 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/16:1(9Z))Pw027832Pw027832 greyscalePw027832 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:0)Pw027833Pw027833 greyscalePw027833 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(11Z))Pw027834Pw027834 greyscalePw027834 simpleNot Available
Cardiolipin Biosynthesis CL(16:0/16:0/16:0/18:1(9Z))Pw027835Pw027835 greyscalePw027835 simpleNot Available
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 IDFDB024162
KNApSAcK IDNot Available
Chemspider ID24765809
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24779567
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