Record Information
Version1.0
Creation date2011-09-21 00:40:52 UTC
Update date2015-07-21 06:58:01 UTC
Primary IDFDB024171
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCDP-DG(18:0/16:0)
DescriptionCDP-DG(18:0/16:0) 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(18:0/16:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-CDPHMDB
1-Stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphateHMDB
CDP-DG(34:0)HMDB
CDP-Diacylglycerol(18:0/16:0)HMDB
CDP-Diacylglycerol(34:0)HMDB
1-octadecanoyl-2-hexadecanoyl-sn-glycero-3-CDPhmdb
1-Stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diateHMDB
1-stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphatehmdb
CDP-DG(18:0/16:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0042 g/LALOGPS
logP6.43ALOGPS
logP10.45ChemAxon
logS-5.4ALOGPS
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 Count44ChemAxon
Refractivity249.41 m³·mol⁻¹ChemAxon
Polarizability108.79 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC46H85N3O15P2
IUPAC name{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
InChI IdentifierInChI=1S/C46H85N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)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/h33-34,38-39,43-45,52-53H,3-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t38-,39-,43+,44?,45-/m1/s1
InChI KeyIYHZDHRWSOSUSF-IOYUWRPMSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(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
Average Molecular Weight982.14
Monoisotopic Molecular Weight981.545593045
Classification
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
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0920000101-426af81b026389a7b4d1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1920000100-8295aaf0aa1e45986b53JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-3931000000-0ded663e7c9de8e820b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0api-0690000203-7dc74fecad22a969e066JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ai-4692200201-a99daac50bd5edacbb1bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0bvi-5921000000-29f93d298b327aac65b6JSpectraViewer
ChemSpider ID24765817
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477921
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06977
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Phosphatidate cytidylyltransferase 2CDS2O95674
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference