ChemFOnt: Showing chemical card for CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000003051)

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

CFc000003051

Molecule Identification

Common Name

CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z))

Definition

CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) 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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of docosahexaenoic acid at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the docosahexaenoic acid 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₅₂H₈₃N₃O₁₅P₂

Average Molecular Weight

1052.174

Monoisotopic Molecular Weight

1051.529942025

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-4,7,10,13,16,19-hexaenoyloxy)-3-(octadec-9-enoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid

Traditional Name

[(2R,3R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-iminopyrimidin-1-yl)oxolan-2-yl]methoxy([(2R)-2-(docosa-4,7,10,13,16,19-hexaenoyloxy)-3-(octadec-9-enoyloxy)propoxy(hydroxy)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)CCC=CCC=CCC=CCC=CCC=CCC=CCC

InChI Identifier

InChI=1S/C52H83N3O15P2/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/h5,7,11,13,17-19,21-23,26,28,32,34,39-40,44-45,49-51,58-59H,3-4,6,8-10,12,14-16,20,24-25,27,29-31,33,35-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/t44-,45-,49+,50?,51-/m1/s1

InChI Key

WBSOVHAXQXGTNF-QFBGIDFLSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

CDP-glycerols

Direct Parent

CDP-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 Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

All Tissues (HMDB: HMDB0007002)

Cellular substructure

Membrane (HMDB: HMDB0007002)
Extracellular (HMDB: HMDB0007002)

Source

Exogenous

Exogenous (HMDB: HMDB0007002)

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: HMDB0007002)

Process

Naturally occurring process

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	7.27	ALOGPS
logP	10.66	ChemAxon
logS	-5.9	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	296.25 m³·mol⁻¹	ChemAxon
Polarizability	114.61 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

FDB024196

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)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (CFc000003051)

MOL for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D MOL for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D SDF for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D-SDF for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

PDB for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D PDB for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

SMILES for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

INCHI for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

Structure for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))

3D Structure for CFc000003051 (CDP-DG(18:1(9Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)))