Record Information
Version1.0
Creation date2011-09-21 00:41:00 UTC
Update date2015-07-21 06:58:01 UTC
Primary IDFDB024183
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCDP-DG(18:1(11Z)/18:1(9Z))
DescriptionCDP-DG(18:1(11Z)/18:1(9Z)) 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)/18:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of oleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. 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-(11Z-octadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-CDPhmdb
1-Vaccenoyl-2-oleoyl-sn-glycero-3-cytidine-5'-diateHMDB
1-vaccenoyl-2-oleoyl-sn-glycero-3-cytidine-5'-diphosphatehmdb
CDP-DG(18:1n7/18:1n9)hmdb
CDP-DG(18:1w7/18:1w9)hmdb
CDP-Diacylglycerol(18:1n7/18:1n9)hmdb
CDP-Diacylglycerol(18:1w7/18:1w9)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0033 g/LALOGPS
logP6.97ALOGPS
logP10.69ChemAxon
logS-5.5ALOGPS
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 Count44ChemAxon
Refractivity272.26 m³·mol⁻¹ChemAxon
Polarizability110.89 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC48H85N3O15P2
IUPAC name{[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-3-(octadec-11-enoyloxy)-2-(octadec-9-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid
InChI IdentifierInChI=1S/C48H85N3O15P2/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/h13,15,18,20,35-36,40-41,45-47,54-55H,3-12,14,16-17,19,21-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/t40-,41-,45+,46?,47-/m1/s1
InChI KeyMJTZWNDRIHJESM-KTSAPKHVSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCC=CCCCCCC)(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)CCCCCCCC=CCCCCCCCC
Average Molecular Weight1006.1471
Monoisotopic Molecular Weight1005.545592089
Classification
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
  • Dicarboxylic acid or derivatives
  • Hydropyrimidine
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Fatty acyl
  • Pyrimidine
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Secondary alcohol
  • Carboxylic acid ester
  • Amino acid or derivatives
  • 1,2-diol
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Azacycle
  • Oxacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • 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 ID24765829
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53477932
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB06989
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