Showing chemical card for PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)) (CFc000267535)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:06:13 UTC

Chemfont ID

CFc000267535

Molecule Identification

Common Name

PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15))

Definition

PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)) is an oxidized phosphatidylcholine (PC or GPCho). Oxidized phosphatidylcholines are glycerophospholipids in which a phosphorylcholine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylcholines belong to a group of biomolecules that have a role as signaling molecules. The biosynthesis of oxidized lipids is mediated by several enzymatic families, including cyclooxygenases (COX), lipoxygenases (LOX) and cytochrome P450s (CYP). Non-enzymatically oxidized lipids are produced by uncontrolled oxidation through free radicals and are considered harmful to human health (PMID: 33329396 ). As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths, saturation and degrees of oxidation attached at the C-1 and C-2 positions. PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)), in particular, consists of one chain of one 13Z,16Z-docosadienoyl at the C-1 position and one chain of 15-oxo-eicosatetraenoyl at the C-2 position. Phospholipids are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling. Similarly to what occurs with phospholipids, the fatty acid distribution at the C-1 and C-2 positions of glycerol within oxidized phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Oxidized PCs can be synthesized via three different routes. In one route, the oxidized PC is synthetized de novo following the same mechanisms as for PCs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidated acyl chains with an oxidated acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PC backbone, mainely through the action of LOX (PMID: 33329396 ).

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

[H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCCC

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INCHI for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

InChI=1S/C50H86NO9P/c1-6-8-10-11-12-13-14-15-16-17-18-19-20-21-24-27-30-33-37-41-49(53)57-45-48(46-59-61(55,56)58-44-43-51(3,4)5)60-50(54)42-38-34-31-28-25-22-23-26-29-32-36-40-47(52)39-35-9-7-2/h12-13,15-16,22-23,28-29,31-32,36,40,48H,6-11,14,17-21,24-27,30,33-35,37-39,41-46H2,1-5H3/b13-12-,16-15-,23-22-,31-28-,32-29-,40-36+/t48-/m1/s1

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Structure for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

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3D Structure for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

Synonyms

Not Available

Chemical Formula

C₅₀H₈₆NO₉P

Average Molecular Weight

876.21

Monoisotopic Molecular Weight

875.604020351

IUPAC Name

(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-{[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(13Z,16Z)-docosa-13,16-dienoyloxy]-2-{[(5Z,8Z,11Z,13E)-15-oxoicosa-5,8,11,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCCCC\C=C/C\C=C/CCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C=C/C(=O)CCCCC

InChI Identifier

InChI=1S/C50H86NO9P/c1-6-8-10-11-12-13-14-15-16-17-18-19-20-21-24-27-30-33-37-41-49(53)57-45-48(46-59-61(55,56)58-44-43-51(3,4)5)60-50(54)42-38-34-31-28-25-22-23-26-29-32-36-40-47(52)39-35-9-7-2/h12-13,15-16,22-23,28-29,31-32,36,40,48H,6-11,14,17-21,24-27,30,33-35,37-39,41-46H2,1-5H3/b13-12-,16-15-,23-22-,31-28-,32-29-,40-36+/t48-/m1/s1

InChI Key

JZUVORUCWUIINN-LPHJASCZSA-N

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

Phosphocholines
Fatty acid esters
Dialkyl phosphates
Dicarboxylic acids and derivatives
Tetraalkylammonium salts
Enones
Acryloyl compounds
Ketones
Carboxylic acid esters
Organopnictogen compounds
Organic salts
Organic oxides
Hydrocarbon derivatives
Amines

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Circulatory system disorder

Vascular disorder

Atherosclerosis (PMID: 21475195)

Endocrine system disorder

Breast disorder

Breast cancer (PMID: 9468591)

Digestive system disorder

Gastrointestinal disorder

Lower gastrointestinal disorder

Ulcerative colitis (PMID: 33440385)

Cancer

Cervical cancer (PMID: 26566624)

Disposition

Biological location

Cell

All cells and tissues (HMDB: HMDB0288019)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0288019)

Golgi apparatus membrane (HMDB: HMDB0288019)
Cell membrane (HMDB: HMDB0288019)

Source

Endogenous

Endogenous (HMDB: HMDB0288019)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylcholine Biosynthesis (HMDB: HMDB0288019)

Cellular process

Apoptosis (PMID: 23350810)
Cell proliferation (PMID: 23350810)

Biochemical process

Lipid transport (PMID: 21979151)

Role

Biological role

Nutrient (PMID: 28411170)

Industrial application

Pharmaceutical industry

Biomarker

Breast cancer ()
Ulcerative colitis ()
Cervical cancer ()
Atherosclerosis ()

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.6e-05 g/L	ALOGPS
logP	5.78	ALOGPS
logP	9.57	ChemAxon
logS	-7.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	128.26 Å²	ChemAxon
Rotatable Bond Count	44	ChemAxon
Refractivity	269.19 m³·mol⁻¹	ChemAxon
Polarizability	105.47 Å³	ChemAxon
Number of Rings	0	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

HMDB0288019

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

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

156993798

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)) (CFc000267535)

MOL for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

3D MOL for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

3D SDF for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

3D-SDF for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

PDB for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

3D PDB for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

SMILES for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

INCHI for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

Structure for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))

3D Structure for CFc000267535 (PC(22:2(13Z,16Z)/20:4(5Z,8Z,11Z,13E)+=O(15)))