Showing chemical card for PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)) (CFc000264534)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:00:57 UTC

Chemfont ID

CFc000264534

Molecule Identification

Common Name

PE(DiMe(9,3)/18:1(12Z)-O(9S,10R))

Definition

PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)) is an oxidized phosphatidylethanolamine (PE). Oxidized phosphatidylethanolamines are glycerophospholipids in which a phosphorylethanolamine moiety occupies a glycerol substitution site and at least one of the fatty acyl chains has undergone oxidation. As all oxidized lipids, oxidized phosphatidylethanolamines 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, phosphatidylethanolamines 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. PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)), in particular, consists of one chain of one 10,13-epoxy-11-methylhexadeca-10,12-dienoyl at the C-1 position and one chain of 9,10-epoxy-octadecenoyl 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 PEs can be synthesized via three different routes. In one route, the oxidized PE is synthetized de novo following the same mechanisms as for PEs 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 PE backbone, mainly through the action of LOX (PMID: 33329396 ).

Structure

MOL SDF PDB SMILES InChI

SMILES for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

[H][C@@](COC(=O)CCCCCCCCC1=C(C)C(C)=C(CCC)O1)(COP(O)(=O)OCCN)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC

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INCHI for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

InChI=1S/C41H72NO10P/c1-5-7-8-9-13-19-25-38-39(52-38)26-20-15-12-17-22-28-41(44)50-35(32-49-53(45,46)48-30-29-42)31-47-40(43)27-21-16-11-10-14-18-24-37-34(4)33(3)36(51-37)23-6-2/h13,19,35,38-39H,5-12,14-18,20-32,42H2,1-4H3,(H,45,46)/b19-13-/t35-,38?,39?/m1/s1

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Structure for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

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3D Structure for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

Synonyms

Value	Source
(2-Aminoethoxy)[(2R)-3-{[9-(3,4-dimethyl-5-propylfuran-2-yl)nonanoyl]oxy}-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphinate	HMDB

Chemical Formula

C₄₁H₇₂NO₁₀P

Average Molecular Weight

769.998

Monoisotopic Molecular Weight

769.48938452

IUPAC Name

(2-aminoethoxy)[(2R)-3-{[9-(3,4-dimethyl-5-propylfuran-2-yl)nonanoyl]oxy}-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy]phosphinic acid

Traditional Name

2-aminoethoxy((2R)-3-{[9-(3,4-dimethyl-5-propylfuran-2-yl)nonanoyl]oxy}-2-[(8-{3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}octanoyl)oxy]propoxy)phosphinic acid

CAS Registry Number

Not Available

SMILES

[H][C@@](COC(=O)CCCCCCCCC1=C(C)C(C)=C(CCC)O1)(COP(O)(=O)OCCN)OC(=O)CCCCCCCC1OC1C\C=C/CCCCC

InChI Identifier

InChI=1S/C41H72NO10P/c1-5-7-8-9-13-19-25-38-39(52-38)26-20-15-12-17-22-28-41(44)50-35(32-49-53(45,46)48-30-29-42)31-47-40(43)27-21-16-11-10-14-18-24-37-34(4)33(3)36(51-37)23-6-2/h13,19,35,38-39H,5-12,14-18,20-32,42H2,1-4H3,(H,45,46)/b19-13-/t35-,38?,39?/m1/s1

InChI Key

MYRQXCSIFOAOHW-YKVJBCIRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phosphatidylethanolamines. These are glycerophosphoetahnolamines in which two fatty acids are bonded to the glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoethanolamines

Direct Parent

Phosphatidylethanolamines

Alternative Parents

Furanoid fatty acids
Phosphoethanolamines
Fatty acid esters
Dialkyl phosphates
Dicarboxylic acids and derivatives
Heteroaromatic compounds
Furans
Carboxylic acid esters
Amino acids and derivatives
Oxacyclic compounds
Epoxides
Dialkyl ethers
Organopnictogen compounds
Organic oxides
Monoalkylamines
Hydrocarbon derivatives
Carbonyl compounds

Substituents

Diacylglycero-3-phosphoethanolamine
Furanoid fatty acid
Phosphoethanolamine
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Heteroaromatic compound
Furan
Carboxylic acid ester
Amino acid or derivatives
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Carbonyl group
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Endocrine system disorder

Diabetes mellitus type 2 (PMID: 30402908)

Digestive system disorder

Hepatobiliary disorder

Hepatic disorder

Non-alcoholic fatty liver disease (PMID: 26811286)

Nervous system disorder

Central nervous system disorder

Alzheimer's Disease (PMID: 26811286)
Parkinson's disease (PMID: 26811286)

Disposition

Biological location

Cell

All cells and tissues (HMDB: HMDB0285018)

Cellular substructure

Organelle

Endoplasmic reticulum (HMDB: HMDB0285018)

Golgi apparatus membrane (HMDB: HMDB0285018)
Cell membrane (HMDB: HMDB0285018)

Source

Endogenous

Endogenous (HMDB: HMDB0285018)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Phosphatidylethanolamine Biosynthesis (HMDB: HMDB0285018)

Biochemical process

Lipid transport (PMID: 26811286)

Cellular process

Autophagy (PMID: 26811286)

Role

Biological role

Nutrient (PMID: 26811286)

Industrial application

Pharmaceutical industry

Biomarker

Diabetes mellitus type 2 ()
Parkinson's disease ()

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0032 g/L	ALOGPS
logP	7	ALOGPS
logP	9.24	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	1.87	ChemAxon
pKa (Strongest Basic)	10	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	160.05 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	210.23 m³·mol⁻¹	ChemAxon
Polarizability	92.2 Å³	ChemAxon
Number of Rings	2	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

HMDB0285018

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

156988370

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)) (CFc000264534)

MOL for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

3D MOL for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

3D SDF for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

3D-SDF for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

PDB for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

3D PDB for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

SMILES for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

INCHI for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

Structure for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))

3D Structure for CFc000264534 (PE(DiMe(9,3)/18:1(12Z)-O(9S,10R)))