ChemFOnt: Showing chemical card for PC(18:1(9Z)e/2:0) (CFc000006782)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:52:52 UTC

Chemfont ID

CFc000006782

Molecule Identification

Common Name

PC(18:1(9Z)e/2:0)

Definition

2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine is an intermediate in ether lipid metabolism. 2-Acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine is converted from 2-acetyl-1-octadecyl-sn-glycerol via diacylglycerol cholinephosphotransferase (EC: 2.7.8.2). This is an ether lipid with platelet-activating factor functions which has an acetyl group instead of an acyl chain at the second position (SN-2). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₈H₅₆NO₇P

Average Molecular Weight

549.7205

Monoisotopic Molecular Weight

549.379439663

IUPAC Name

(2-{[(2R)-2-(acetyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-(acetyloxy)-3-(octadec-9-en-1-yloxy)propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

None

SMILES

[H][C@@](COCCCCCCCCC=CCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(C)=O

InChI Identifier

InChI=1S/C28H56NO7P/c1-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-23-33-25-28(36-27(2)30)26-35-37(31,32)34-24-22-29(3,4)5/h13-14,28H,6-12,15-26H2,1-5H3/t28-/m1/s1

InChI Key

ZBOQHUSCQCEBGK-MUUNZHRXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-alkyl,2-acetylglycero-3-phosphocholines. These are glycerophosphocholines that carry exactly one acetyl chain attached to the glycerol moiety through an ester linkage at the O2-position, and one alkyl chain attached through an ether linkage at the O1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-alkyl,2-acetylglycero-3-phosphocholines

Alternative Parents

Substituents

1-alkyl,2-acetylglycero-3-phosphocholine
Phosphocholine
Glycerol ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011148)
Membrane (HMDB: HMDB0011148)

Source

Exogenous

Exogenous (HMDB: HMDB0011148)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0011148)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	3.14	ALOGPS
logP	2.54	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	94.12 Å²	ChemAxon
Rotatable Bond Count	27	ChemAxon
Refractivity	161.99 m³·mol⁻¹	ChemAxon
Polarizability	66.06 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB027923

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

57369896

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PC(18:1(9Z)e/2:0) (CFc000006782)

MOL for CFc000006782 (PC(18:1(9Z)e/2:0))

3D MOL for CFc000006782 (PC(18:1(9Z)e/2:0))

3D SDF for CFc000006782 (PC(18:1(9Z)e/2:0))

3D-SDF for CFc000006782 (PC(18:1(9Z)e/2:0))

PDB for CFc000006782 (PC(18:1(9Z)e/2:0))

3D PDB for CFc000006782 (PC(18:1(9Z)e/2:0))

SMILES for CFc000006782 (PC(18:1(9Z)e/2:0))

INCHI for CFc000006782 (PC(18:1(9Z)e/2:0))

Structure for CFc000006782 (PC(18:1(9Z)e/2:0))

3D Structure for CFc000006782 (PC(18:1(9Z)e/2:0))