CDP-DG(14:1(11Z)/24:1(9Z)) (YMDB12178)

Identification

YMDB ID

YMDB12178

Name

CDP-DG(14:1(11Z)/24:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

CDP-DG(14:1(11Z)/24:1(9Z)) belongs to the family of CDP-diacylglycerols. It is a glycerophospholipid containing a diacylglycerol, with a cytidine diphosphate attached to the oxygen O1 or O2 of the glycerol part. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. CDP-DG(14:1(11Z)/24:1(9Z)), in particular, consists of two 11Z-tetradecenoyl chain at positions C-1 and C2. In E. coli glycerophospholipid metabolism, The biosynthesis of CDP-diacylglycerol (CDP-DG) involves condensation of phosphatidic acid (PA) and cytidine triphosphate, with elimination of pyrophosphate, catalysed by the enzyme CDP-diacylglycerol synthase. The resulting CDP-diacylglycerol can be utilized immediately for the synthesis of phosphatidylglycerol (PG), and thence cardiolipin (CL), and of phosphatidylinositol (PI). CDP-DG(14:1(11Z)/24:1(9Z)) is also a substrate of CDP-diacylglycerol pyrophosphatase. It is involved in CDP-diacylglycerol degradation pathway.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 1034.216
Monoisotopic: 1033.576893174

InChI Key

RZYYVBLCQJBJEG-YLRVUMIKSA-N

InChI

InChI=1S/C50H89N3O15P2/c1-3-5-7-9-11-13-15-16-17-18-19-20-21-22-23-24-26-28-30-32-34-36-46(55)66-42(39-63-45(54)35-33-31-29-27-25-14-12-10-8-6-4-2)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/h6,8,22-23,37-38,42-43,47-49,56-57H,3-5,7,9-21,24-36,39-41H2,1-2H3,(H,59,60)(H,61,62)(H2,51,52,58)/b8-6-,23-22-/t42-,43-,47+,48?,49-/m1/s1

IUPAC Name

{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[(2R)-2-[(9Z)-tetracos-9-enoyloxy]-3-[(11Z)-tetradec-11-enoyloxy]propoxy]phosphoryl}oxy)phosphinic acid

Traditional IUPAC Name

[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy([hydroxy((2R)-2-[(9Z)-tetracos-9-enoyloxy]-3-[(11Z)-tetradec-11-enoyloxy]propoxy)phosphoryl]oxy)phosphinic acid

Chemical Formula

C₅₀H₈₉N₃O₁₅P₂

SMILES

[H][C@@](COC(=O)CCCCCCCCC\C=C/CC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCC

Chemical Taxonomy

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0018 g/L	ALOGPS
logP	7.29	ALOGPS
logP	11.5	ChemAxon
logS	-5.8	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	46	ChemAxon
Refractivity	270.05 m³·mol⁻¹	ChemAxon
Polarizability	114.78 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Mitochondrion membrane

Organoleptic Properties

Not Available

SMPDB Pathways

Cardiolipin Biosynthesis CL(10:0/12:0/14:1(11Z)/24:1(9Z))	PW003762
Cardiolipin Biosynthesis CL(10:0/14:0/14:1(11Z)/24:1(9Z))	PW004034
Cardiolipin Biosynthesis CL(10:0/14:1(11Z)/14:1(11Z)/24:1(9Z))	PW004276
Cardiolipin Biosynthesis CL(10:0/14:1(9Z)/14:1(11Z)/24:1(9Z))	PW004517
Cardiolipin Biosynthesis CL(12:0/12:0/14:1(11Z)/24:1(9Z))	PW005905

KEGG Pathways

Not Available

SMPDB Reactions

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-1911001000-2e56f7e23ea29f91b675	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2901000100-c273bf23117ab17677e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3911000000-db2f565e2544b40c1db6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2984002012-6af63356d646ab135a2c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vi-8984210110-88564723c8b424700949	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvi-5911000000-a06bf03bd6109fbfe583	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Cardiolipin synthase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol
Gene Name:: CRD1
Uniprot ID:: Q07560
Molecular weight:: 32019.30078

Reactions

2 Phosphatidylglycerol → diphosphatidylglycerol + glycerol.

Structure for #<Compound:0xa0c6c26c>

Enzymes

Reactions