Showing chemical card for PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)) (CFc000269131)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:09:16 UTC

Chemfont ID

CFc000269131

Molecule Identification

Common Name

PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17))

Definition

PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)) 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(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)), in particular, consists of one chain of one 1Z-octadecenyl at the C-1 position and one chain of 16,17-epoxy-docosapentaenoyl 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 CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

[H][C@@](CO\C=C\CCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/CC1OC1C\C=C/CC

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INCHI for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

InChI=1S/C48H84NO8P/c1-6-8-10-11-12-13-14-15-16-17-20-23-26-29-32-36-41-53-43-45(44-55-58(51,52)54-42-40-49(3,4)5)56-48(50)39-35-31-28-25-22-19-18-21-24-27-30-34-38-47-46(57-47)37-33-9-7-2/h9,19,21-22,24,28,30-31,33-34,36,41,45-47H,6-8,10-18,20,23,25-27,29,32,35,37-40,42-44H2,1-5H3/b22-19-,24-21-,31-28-,33-9-,34-30-,41-36+/t45-,46?,47?/m1/s1

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Structure for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

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3D Structure for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

Synonyms

Not Available

Chemical Formula

C₄₈H₈₄NO₈P

Average Molecular Weight

834.173

Monoisotopic Molecular Weight

833.593455667

IUPAC Name

trimethyl(2-{[(2R)-3-[(1E)-octadec-1-en-1-yloxy]-2-{[(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)azanium

Traditional Name

trimethyl(2-{[(2R)-3-[(1E)-octadec-1-en-1-yloxy]-2-{[(4Z,7Z,10Z,13Z)-15-{3-[(2Z)-pent-2-en-1-yl]oxiran-2-yl}pentadeca-4,7,10,13-tetraenoyl]oxy}propyl phosphono]oxy}ethyl)azanium

CAS Registry Number

Not Available

SMILES

[H][C@@](CO\C=C\CCCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/CC1OC1C\C=C/CC

InChI Identifier

InChI=1S/C48H84NO8P/c1-6-8-10-11-12-13-14-15-16-17-20-23-26-29-32-36-41-53-43-45(44-55-58(51,52)54-42-40-49(3,4)5)56-48(50)39-35-31-28-25-22-19-18-21-24-27-30-34-38-47-46(57-47)37-33-9-7-2/h9,19,21-22,24,28,30-31,33-34,36,41,45-47H,6-8,10-18,20,23,25-27,29,32,35,37-40,42-44H2,1-5H3/b22-19-,24-21-,31-28-,33-9-,34-30-,41-36+/t45-,46?,47?/m1/s1

InChI Key

ZWKHVNAACOLZRP-LTMGBUQYSA-N

Chemical Taxonomy

Classification

Not classified

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: HMDB0289615)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0289615)

Golgi apparatus membrane (HMDB: HMDB0289615)
Cell membrane (HMDB: HMDB0289615)

Source

Endogenous

Endogenous (HMDB: HMDB0289615)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylcholine Biosynthesis (HMDB: HMDB0289615)

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	3.7e-05 g/L	ALOGPS
logP	6.32	ALOGPS
logP	8.95	ChemAxon
logS	-7.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	106.65 Å²	ChemAxon
Rotatable Bond Count	41	ChemAxon
Refractivity	258.12 m³·mol⁻¹	ChemAxon
Polarizability	101.61 Å³	ChemAxon
Number of Rings	1	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

HMDB0289615

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)) (CFc000269131)

MOL for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

3D MOL for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

3D SDF for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

3D-SDF for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

PDB for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

3D PDB for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

SMILES for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

INCHI for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

Structure for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))

3D Structure for CFc000269131 (PC(P-18:0/22:5(4Z,7Z,10Z,13Z,19Z)-O(16,17)))