| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 19:12:38 -0600 |
| Update Date |
2013-02-08 17:15:36 -0700 |
| HMDB ID |
HMDB06988 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
CDP-DG(18:1(11Z)/18:1(11Z)) |
| Description |
CDP-DG(18:1(11Z)/18:1(11Z)) 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(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the vaccenic acid moiety is derived from butter fat and animal fat. 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1,2-Di(11Z-octadecenoyl)-rac-glycero-3-CDP
- 1,2-Divaccenoyl-rac-glycero-3-cytidine-5'-diphosphate
- CDP-DG(18:1/18:1)
- CDP-DG(18:1n7/18:1n7)
- CDP-DG(18:1w7/18:1w7)
- CDP-DG(36:2)
- CDP-Diacylglycerol(18:1/18:1)
- CDP-Diacylglycerol(18:1n7/18:1n7)
- CDP-Diacylglycerol(18:1w7/18:1w7)
- CDP-Diacylglycerol(36:2)
|
| Chemical Formula |
C48H85N3O15P2 |
| Average Molecular Weight |
1006.1471 |
| Monoisotopic Molecular Weight |
1005.545592089 |
| 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)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxy]phosphinic acid |
| Traditional IUPAC Name |
{[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2,3-bis[(11Z)-octadec-11-enoyloxy]propoxyphosphinic acid |
| CAS Registry Number |
Not Available |
| SMILES |
[H][C@@](COC(=O)CCCCCCCCC\C=C/CCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCC\C=C/CCCCCC |
| InChI Identifier |
InChI=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/h13-16,35-36,40-41,45-47,54-55H,3-12,17-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b15-13-,16-14-/t40-,41-,45+,46?,47-/m1/s1 |
| InChI Key |
KISJWPWNABZPGN-PYYNXHAWSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerophospholipids |
| Sub Class |
CDP-Glycerols |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- Organic Compounds
|
| Substituents |
- 1,2 Diol
- Aminopyrimidine
- Carboxylic Acid Ester
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Glycosyl Compound
- Hydropyrimidine
- Monosaccharide Phosphate
- N Glycosyl Compound
- Organic Hypophosphite
- Organic Phosphite
- Organic Pyrophosphate
- Oxolane
- Pentose Monosaccharide
- Phosphoric Acid Ester
- Pyrimidine
- Pyrimidine Ribonucleoside Diphosphate
- Pyrimidone
- Saccharide
- Secondary Alcohol
|
| Direct Parent |
CDP-Diacylglycerols |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
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| Biological Properties |
|---|
| Cellular Locations |
|
| Biofluid Locations |
Not Available
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| Tissue Location |
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| DrugBank Metabolite ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB024182 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24765828  |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB06988 |
| Metagene Link |
HMDB06988 |
| METLIN ID |
Not Available |
| PubChem Compound |
24779568 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
Not Available |
