ChemFOnt: Showing chemical card for CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000003048)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:48:04 UTC

Chemfont ID

CFc000003048

Molecule Identification

Common Name

CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z))

Definition

CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) 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)/20:4(5Z,8Z,11Z,14Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of arachidonic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the arachidonic acid moiety is derived from animal fats and eggs. 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

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₀H₈₃N₃O₁₅P₂

Average Molecular Weight

1028.1526

Monoisotopic Molecular Weight

1027.529942025

IUPAC Name

{[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({hydroxy[(2R)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-enoyloxy)propoxy]phosphoryl}oxy)phosphinic acid

Traditional Name

[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy([hydroxy((2R)-2-(icosa-5,8,11,14-tetraenoyloxy)-3-(octadec-9-enoyloxy)propoxy)phosphoryl]oxy)phosphinic acid

CAS Registry Number

None

SMILES

[H][C@@](COC(=O)CCCCCCCC=CCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(=N)N=C2O)C([H])(O)[C@@]1([H])O)OC(=O)CCCC=CCC=CCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C50H83N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2)40-64-69(59,60)68-70(61,62)65-41-43-47(56)48(57)49(67-43)53-38-37-44(51)52-50(53)58/h11,13,17-19,21-22,24,28,30,37-38,42-43,47-49,56-57H,3-10,12,14-16,20,23,25-27,29,31-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/t42-,43-,47+,48?,49-/m1/s1

InChI Key

JHMUAQLWUZUICD-HKRBFXDCSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Substituents

Diacylglycero-3-phosphoethanolamine
Phosphoethanolamine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Amino acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Primary aliphatic amine
Organic nitrogen compound
Primary amine
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

All Tissues (HMDB: HMDB0006999)

Cellular substructure

Membrane (HMDB: HMDB0006999)
Extracellular (HMDB: HMDB0006999)

Source

Exogenous

Exogenous (HMDB: HMDB0006999)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0006999)

Process

Naturally occurring process

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0023 g/L	ALOGPS
logP	7.13	ALOGPS
logP	10.49	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	2.55	ChemAxon
pKa (Strongest Basic)	1.78	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	264.26 Å²	ChemAxon
Rotatable Bond Count	43	ChemAxon
Refractivity	284.81 m³·mol⁻¹	ChemAxon
Polarizability	110.85 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024193

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)) (CFc000003048)

MOL for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

3D MOL for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

3D SDF for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

3D-SDF for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

PDB for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

3D PDB for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

SMILES for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

INCHI for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

Structure for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))

3D Structure for CFc000003048 (CDP-DG(18:1(9Z)/20:4(5Z,8Z,11Z,14Z)))