CDP-DG(14:1(11Z)/22:0) (YMDB12173)

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Identification

YMDB ID

YMDB12173

Name

CDP-DG(14:1(11Z)/22:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

CDP-DG(14:1(11Z)/22:0) 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)/22:0), 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)/22:0) 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: 1008.178
Monoisotopic: 1007.561243109

InChI Key

MNSNMJHGXRMGAU-HGSPZUAQSA-N

InChI

InChI=1S/C48H87N3O15P2/c1-3-5-7-9-11-13-15-16-17-18-19-20-21-22-24-26-28-30-32-34-44(53)64-40(37-61-43(52)33-31-29-27-25-23-14-12-10-8-6-4-2)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/h6,8,35-36,40-41,45-47,54-55H,3-5,7,9-34,37-39H2,1-2H3,(H,57,58)(H,59,60)(H2,49,50,56)/b8-6-/t40-,41-,45+,46?,47-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

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

Chemical Formula

C₄₈H₈₇N₃O₁₅P₂

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)CCCCCCCCCCCCCCCCCCCCC

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	0.0026 g/L	ALOGPS
logP	6.92	ALOGPS
logP	10.97	ChemAxon
logS	-5.6	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	45	ChemAxon
Refractivity	259.73 m³·mol⁻¹	ChemAxon
Polarizability	112.43 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(10:0/14:0/14:1(11Z)/22:0)	PW004029
Cardiolipin Biosynthesis CL(10:0/14:1(11Z)/14:1(11Z)/22:0)	PW004271
Cardiolipin Biosynthesis CL(10:0/14:1(9Z)/14:1(11Z)/22:0)	PW004512
Cardiolipin Biosynthesis CL(12:0/12:0/14:1(11Z)/22:0)	PW005900
Cardiolipin Biosynthesis CL(12:0/14:0/14:1(11Z)/22:0)	PW006138

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-0911001000-381e1bc2333bc610ff0f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1911001000-4b6421e1a7bc42cd55b3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-3921000000-c9c3165baaa98ffc5aad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1983002102-87703b43eac4f10866e1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06vi-6984210301-531401dd4e5a6ae05b28	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bvi-5911000000-e94349fc1ede02b29a6b	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. CDP-diacylglycerol--glycerol-3-phosphate 3-phosphatidyltransferase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Essential for the viability of mitochondrial petite mutant. Catalyzes the committed step to the synthesis of the acidic phospholipids
Gene Name:: PGS1
Uniprot ID:: P25578
Molecular weight:: 59369.69922

Reactions

CDP-diacylglycerol + sn-glycerol 3-phosphate → CMP + 3(3-sn-phosphatidyl)-sn-glycerol 1-phosphate.

Protein Details

2. Phosphatidate cytidylyltransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade
Gene Name:: CDS1
Uniprot ID:: P38221
Molecular weight:: 51822.39844

Reactions

CTP + phosphatidate → diphosphate + CDP-diacylglycerol.

Protein Details

3. 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.

Protein Details

4. Phosphatidate cytidylyltransferase, mitochondrial

General function:: CDP-diacylglycerol biosynthetic process
Specific function:: Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
Gene Name:: TAM41
Uniprot ID:: P53230
Molecular weight:: 44199.33

Reactions

Structure for #<Compound:0xab98b088>

Enzymes

Reactions

Reactions

Reactions

Reactions