PC(18:2(9Z,11Z)/18:2(9Z,11Z)) (YMDB15897)

Identification

YMDB ID

YMDB15897

Name

PC(18:2(9Z,11Z)/18:2(9Z,11Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:2(9Z,11Z)/18:2(9Z,11Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(18:2(9Z,11Z)/18:2(9Z,11Z)), in particular, consists of two 9Z,11Z-octadecadienoyl chains at positions C-1 and C-2. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 782.097
Monoisotopic: 781.562155538

InChI Key

FDJMFFOKIXCKTF-MMWMKIJTSA-N

InChI

InChI=1S/C44H80NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h16-23,42H,6-15,24-41H2,1-5H3/b18-16-,19-17-,22-20-,23-21-/t42-/m1/s1

IUPAC Name

(2-{[(2R)-2,3-bis[(9Z,11Z)-octadeca-9,11-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional IUPAC Name

(2-{[(2R)-2,3-bis[(9Z,11Z)-octadeca-9,11-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Chemical Formula

C₄₄H₈₀NO₈P

SMILES

[H][C@@](COC(=O)CCCCCCC\C=C/C=C\CCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C=C\CCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphocholines (LMGP01010930 )

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	3.1e-05 g/L	ALOGPS
logP	5.73	ALOGPS
logP	8.44	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	238.74 m³·mol⁻¹	ChemAxon
Polarizability	94.83 Å³	ChemAxon
Number of Rings	0	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

Endoplasmic reticulum
Mitochondria

Organoleptic Properties

Not Available

SMPDB Pathways

Lysolipid incorporation into ER PC(18:2(9Z,11Z)/18:2(9Z,11Z))	PW002789
Lysolipid incorporation into Mitochondria PC(18:2(9Z,11Z)/18:2(9Z,11Z))	PW002797

KEGG Pathways

Not Available

SMPDB Reactions

Citicoline + DG(14:0/14:0/0:0) → Cytidine monophosphate + hydron + PC(18:2(9Z,11Z)/18:2(9Z,11Z))

PC(14:0/0:0) → PC(18:2(9Z,11Z)/18:2(9Z,11Z))

PE-NMe2(18:2(9Z,11Z)/18:2(9Z,11Z)) + S-Adenosyl-L-methionine → S-Adenosylhomocysteine + hydron + PC(18:2(9Z,11Z)/18:2(9Z,11Z))

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
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	24778970
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Cholinephosphotransferase 1

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:: CPT1
Uniprot ID:: P17898
Molecular weight:: 44829.0

Reactions

CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.

Protein Details

2. Methylene-fatty-acyl-phospholipid synthase

General function:: Involved in N-methyltransferase activity
Specific function:: S-adenosyl-L-methionine + phospholipid olefinic fatty acid = S-adenosyl-L-homocysteine + phospholipid methylene fatty acid
Gene Name:: OPI3
Uniprot ID:: P05375
Molecular weight:: 23150.09961

Reactions

S-adenosyl-L-methionine + phospholipid olefinic fatty acid → S-adenosyl-L-homocysteine + phospholipid methylene fatty acid.

Structure for #<Compound:0xac512d0c>

Enzymes

Reactions

Reactions