Record Information
Version1.0
Creation date2011-09-21 00:41:13 UTC
Update date2015-07-21 06:58:01 UTC
Primary IDFDB024195
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCDP-DG(18:1(9Z)/22:3(10Z,13Z,16Z))
DescriptionCDP-DG(18:1(9Z)/22:3(10Z,13Z,16Z)) 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(9Z)/22:3(10Z,13Z,16Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the (10Z,13Z,16Z-docosatrienoyl) 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. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-(9Z-octadecenoyl)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-CDPhmdb
1-Oleoyl-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-cytidine-5'-diateHMDB
1-oleoyl-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-cytidine-5'-diphosphatehmdb
CDP-DG(18:1n9/22:3n6)hmdb
CDP-DG(18:1w9/22:3w6)hmdb
CDP-Diacylglycerol(18:1n9/22:3n6)hmdb
CDP-Diacylglycerol(18:1w9/22:3w6)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0018 g/LALOGPS
logP7.46ALOGPS
logP11.74ChemAxon
logS-5.8ALOGPS
pKa (Strongest Acidic)2.55ChemAxon
pKa (Strongest Basic)1.78ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area264.26 ŲChemAxon
Rotatable Bond Count46ChemAxon
Refractivity292.9 m³·mol⁻¹ChemAxon
Polarizability117.01 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC52H89N3O15P2
IUPAC name{[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[(2R)-2-(docosa-10,13,16-trienoyloxy)-3-(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid
InChI IdentifierInChI=1S/C52H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h11,13,17-19,21-23,39-40,44-45,49-51,58-59H,3-10,12,14-16,20,24-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/t44-,45-,49+,50?,51-/m1/s1
InChI KeyKTDSFHYGTNRDNM-QFBGIDFLSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@]([H])(C(O)[C@@]1([H])O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC=CCC=CCC=CCCCCC
Average Molecular Weight1058.2217
Monoisotopic Molecular Weight1057.576892217
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-5-phosphate
  • Pentose phosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Pentose monosaccharide
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Pyrimidone
  • Fatty acid ester
  • Aminopyrimidine
  • Fatty acyl
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Hydropyrimidine
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • 1,2-diol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
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
SpectraNot Available
ChemSpider ID24765841
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477944
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB07001
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