ChemFOnt: Showing chemical card for CDP-DG(18:0/16:0) (CFc000003026)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:48:02 UTC

Chemfont ID

CFc000003026

Molecule Identification

Common Name

CDP-DG(18:0/16:0)

Definition

CDP-DG(18:0/16:0) 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(18:0/16:0), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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

Value	Source
1-Octadecanoyl-2-hexadecanoyl-sn-glycero-3-CDP	HMDB
1-Stearoyl-2-palmitoyl-sn-glycero-3-cytidine-5'-diphosphate	HMDB
CDP-DG(34:0)	HMDB
CDP-Diacylglycerol(18:0/16:0)	HMDB
CDP-Diacylglycerol(34:0)	HMDB

Chemical Formula

C₄₆H₈₅N₃O₁₅P₂

Average Molecular Weight

982.14

Monoisotopic Molecular Weight

981.545593045

IUPAC Name

{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)phosphinic acid

Traditional Name

[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([(2R)-2-(hexadecanoyloxy)-3-(octadecanoyloxy)propoxy(hydroxy)phosphoryl]oxy)phosphinic acid

CAS Registry Number

None

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCCCCCCCCC

InChI Identifier

InChI=1S/C46H85N3O15P2/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-41(50)59-35-38(62-42(51)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2)36-60-65(55,56)64-66(57,58)61-37-39-43(52)44(53)45(63-39)49-34-33-40(47)48-46(49)54/h33-34,38-39,43-45,52-53H,3-32,35-37H2,1-2H3,(H,55,56)(H,57,58)(H2,47,48,54)/t38-,39-,43+,44?,45-/m1/s1

InChI Key

IYHZDHRWSOSUSF-IOYUWRPMSA-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 phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Aminopyrimidine
Fatty acid ester
Pyrimidone
Monoalkyl phosphate
Imidolactam
Pyrimidine
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Dicarboxylic acid or derivatives
Hydropyrimidine
Organic phosphoric acid derivative
Monosaccharide
Tetrahydrofuran
Heteroaromatic compound
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid ester
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Alcohol
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Amine
Carbonyl group
Primary amine
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Organoleptic effect

Touch

Smooth (HMDB: HMDB0006977)

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0006977)
Extracellular (HMDB: HMDB0006977)
Cytoplasm (HMDB: HMDB0006977)
Cell membrane (HMDB: HMDB0006977)
Intracellular membrane (HMDB: HMDB0006977)

Organelle

Mitochondrion (HMDB: HMDB0006977)

Tissue

All Tissues (HMDB: HMDB0006977)
All Tissues (HMDB: HMDB0006977)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0006977)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006977)

Source

Endogenous

Endogenous (HMDB: HMDB0006977)

Animal

Animal (HMDB: HMDB0006977)

Exogenous

Food

Food (HMDB: HMDB0006977)

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)

Exogenous (HMDB: HMDB0006977)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006977)

Biochemical pathway

Metabolic pathway

Cardiolipin Biosynthesis (HMDB: HMDB0006977)
Cardiolipin Biosynthesis CL(16:0/16:1(9Z)/18:0/16:0) (PathBank: SMP0068522)
Cardiolipin Biosynthesis CL(16:0/18:2(9Z,12Z)/18:0/16:0) (PathBank: SMP0068718)
Cardiolipin Biosynthesis CL(16:0/20:4(5Z,8Z,11Z,14Z)/18:0/16:0) (PathBank: SMP0068760)
Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:0) (PathBank: SMP0069378)
Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/16:1(9Z)) (PathBank: SMP0069379)
Cardiolipin Biosynthesis CL(18:0/16:0/16:1(9Z)/18:0) (PathBank: SMP0069380)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:0) (PathBank: SMP0069381)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(9Z)) (PathBank: SMP0069385)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0069388)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(11Z)) (PathBank: SMP0069397)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:1(9Z)) (PathBank: SMP0069398)
Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:2(9Z,12Z)) (PathBank: SMP0069401)
Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/16:0) (PathBank: SMP0069402)
Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0069404)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069408)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069412)
Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0069413)
Cardiolipin Biosynthesis CL(16:0/18:1(9Z)/18:0/16:0) (PathBank: SMP0077412)
Cardiolipin Biosynthesis CL(16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0/16:0) (PathBank: SMP0077550)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:0) (PathBank: SMP0078132)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:1(11Z)) (PathBank: SMP0078133)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:0) (PathBank: SMP0078141)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(11Z)) (PathBank: SMP0078142)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/18:1(9Z)) (PathBank: SMP0078143)
Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/16:0) (PathBank: SMP0078148)
Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078164)
Cardiolipin Biosynthesis CL(16:0/18:1(11Z)/18:0/16:0) (PathBank: SMP0092629)
Cardiolipin Biosynthesis CL(16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0/16:0) (PathBank: SMP0092875)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/18:2(9Z,12Z)) (PathBank: SMP0093407)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/20:4(5Z,8Z,11Z,14Z)) (PathBank: SMP0093408)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/16:0) (PathBank: SMP0093416)
Cardiolipin Biosynthesis CL(18:0/16:0/20:4(5Z,8Z,11Z,14Z)/18:0) (PathBank: SMP0093424)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0093432)
Cardiolipin Biosynthesis CL(18:0/16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0093435)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(9Z)/18:0) (PathBank: SMP0069396)
Cardiolipin Biosynthesis CL(18:0/16:0/18:2(9Z,12Z)/18:0) (PathBank: SMP0069400)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/16:0) (PathBank: SMP0069405)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/18:0) (PathBank: SMP0069406)
Cardiolipin Biosynthesis CL(16:0/18:0/18:0/16:0) (PathBank: SMP0077310)
Cardiolipin Biosynthesis CL(16:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/18:0/16:0) (PathBank: SMP0077653)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:6(4Z,7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0078139)
Cardiolipin Biosynthesis CL(16:0/16:0/18:0/16:0) (PathBank: SMP0092445)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/16:1(9Z)) (PathBank: SMP0093403)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/18:0) (PathBank: SMP0093431)
Cardiolipin Biosynthesis CL(18:0/16:0/18:0/22:5(7Z,10Z,13Z,16Z,19Z)) (PathBank: SMP0069389)
Cardiolipin Biosynthesis CL(18:0/16:0/18:1(11Z)/16:0) (PathBank: SMP0069391)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(7Z,10Z,13Z,16Z,19Z)/16:0) (PathBank: SMP0069409)
Cardiolipin Biosynthesis CL(18:0/16:0/22:5(4Z,7Z,10Z,13Z,16Z)/22:5(4Z,7Z,10Z,13Z,16Z)) (PathBank: SMP0078156)
Phospholipid Biosynthesis CL(18:0/16:0/18:0/16:0) (PathBank: SMP0122064)

Lipid metabolism pathway (HMDB: HMDB0006977)

Cellular process

Cell signaling (HMDB: HMDB0006977)

Biochemical process

Lipid transport (HMDB: HMDB0006977)

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006977)

Food and nutrition

Food additive (HMDB: HMDB0006977)

Biological role

Membrane stabilizer (HMDB: HMDB0006977)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0042 g/L	ALOGPS
logP	6.43	ALOGPS
logP	10.45	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-0.032	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	263.27 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	249.41 m³·mol⁻¹	ChemAxon
Polarizability	108.79 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

HMDB0006977

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024171

KNApSAcK ID

Not Available

Chemspider ID

24765817

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53477921

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for CDP-DG(18:0/16:0) (CFc000003026)

MOL for CFc000003026 (CDP-DG(18:0/16:0))

3D MOL for CFc000003026 (CDP-DG(18:0/16:0))

3D SDF for CFc000003026 (CDP-DG(18:0/16:0))

3D-SDF for CFc000003026 (CDP-DG(18:0/16:0))

PDB for CFc000003026 (CDP-DG(18:0/16:0))

3D PDB for CFc000003026 (CDP-DG(18:0/16:0))

SMILES for CFc000003026 (CDP-DG(18:0/16:0))

INCHI for CFc000003026 (CDP-DG(18:0/16:0))

Structure for CFc000003026 (CDP-DG(18:0/16:0))

3D Structure for CFc000003026 (CDP-DG(18:0/16:0))