ChemFOnt: Showing chemical card for PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)) (CFc000262360)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 02:56:32 UTC

Chemfont ID

CFc000262360

Molecule Identification

Common Name

PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z))

Definition

PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)) is an oxidized phosphatidylserine (PS). Oxidized phosphatidylserines are glycerophospholipids in which a phosphorylserine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylserines 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, phosphatidylserines 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. PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)), in particular, consists of one chain of one Lipoxin A5 at the C-1 position and one chain of 5Z,8Z,11Z,14Z,17Z-eicosapentaenoyl 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 PSs can be synthesized via three different routes. In one route, the oxidized PS is synthetized de novo following the same mechanisms as for PSs but incorporating oxidized acyl chains (PMID: 33329396 ). An alternative is the transacylation of one of the non-oxidized acyl chains with an oxidized acylCoA (PMID: 33329396 ). The third pathway results from the oxidation of the acyl chain while still attached to the PS backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₆H₇₀NO₁₃P

Average Molecular Weight

876.034

Monoisotopic Molecular Weight

875.458478316

IUPAC Name

(2S)-2-amino-3-({hydroxy[(2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-{[(5S,6S,7Z,9Z,11E,13E,15R,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy]phosphoryl}oxy)propanoic acid

Traditional Name

(2S)-2-amino-3-{[hydroxy((2R)-2-[(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyloxy]-3-{[(5S,6S,7Z,9Z,11E,13E,15R,17Z)-5,6,15-trihydroxyicosa-7,9,11,13,17-pentaenoyl]oxy}propoxy)phosphoryl]oxy}propanoic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCC[C@H](O)[C@@H](O)\C=C/C=C\C=C\C=C\[C@H](O)C\C=C/CC)(COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC

InChI Identifier

InChI=1S/C46H70NO13P/c1-3-5-7-8-9-10-11-12-13-14-15-16-17-18-19-24-28-34-45(52)60-40(37-58-61(55,56)59-38-41(47)46(53)54)36-57-44(51)35-29-33-43(50)42(49)32-27-23-21-20-22-26-31-39(48)30-25-6-4-2/h5-7,9-10,12-13,15-16,18-23,25-27,31-32,39-43,48-50H,3-4,8,11,14,17,24,28-30,33-38,47H2,1-2H3,(H,53,54)(H,55,56)/b7-5-,10-9-,13-12-,16-15-,19-18-,22-20+,23-21-,25-6-,31-26+,32-27-/t39-,40-,41+,42+,43+/m1/s1

InChI Key

OBNWVWUSXKIDKW-BRZHZYNBSA-N

Chemical Taxonomy

Classification

Not classified

Functional Ontology

Not Available

All cells and tissues (HMDB: HMDB0282844)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0282844)

Golgi apparatus membrane (HMDB: HMDB0282844)
Cell membrane (HMDB: HMDB0282844)

Source

Endogenous

Endogenous (HMDB: HMDB0282844)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylserine biosynthesis (HMDB: HMDB0282844)

Role

Biological role

Nutrient (PMID: 15979148)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00086 g/L	ALOGPS
logP	2.83	ALOGPS
logP	5.89	ChemAxon
logS	-6	ALOGPS
pKa (Strongest Acidic)	1.47	ChemAxon
pKa (Strongest Basic)	9.38	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	232.37 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	249.2 m³·mol⁻¹	ChemAxon
Polarizability	96.16 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

HMDB0282844

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 PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)) (CFc000262360)

MOL for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

3D MOL for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

3D SDF for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

3D-SDF for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

PDB for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

3D PDB for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

SMILES for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

INCHI for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

Structure for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))

3D Structure for CFc000262360 (PS(20:5(7Z,9Z,11E,13E,17Z)-3OH(5,6,15)/20:5(5Z,8Z,11Z,14Z,17Z)))