Showing Compound LysoPC(O-18:0) (FDB027924)

Record Information

Version

1.0

Creation date

2011-09-21 01:32:04 UTC

Update date

2015-07-21 06:59:16 UTC

Primary ID

FDB027924

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

LysoPC(O-18:0)

Description

1-Octadecyl-sn-glycero-3-phosphocholine is an intermediate in the ether lipid metabolism pathway. 1-Octadecyl-sn-glycero-3-phosphocholine is irreversibly produced from 2-acetyl-1-(9Z-octadecenyl)-sn-glycero-3-phosphocholine via the enzyme 1-alkyl-2-acetylglycerophosphocholine esterase (EC 3.1.1.47). 1-Octadecyl-sn-glycero-3-phosphocholine is an ether phospho-ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol are bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Plasmalogens are glycerol ether phospholipids. They are of two types, alkyl ether (-O-CH2-) and alkenyl ether (-O-CH=CH-). Dihydroxyacetone phosphate (DHAP) serves as the glycerol precursor for the synthesis of plasmalogens. Three major classes of plasmalogens have been identified: choline, ethanolamine and serine derivatives. Ethanolamine plasmalogen is prevalent in myelin. Choline plasmalogen is abundant in cardiac tissue. Usually, the highest proportion of the plasmalogen form is in the ethanolamine class with rather less in choline, and commonly little or none in other phospholipids such as phosphatidylinositol. In choline plasmalogens of most tissues, a higher proportion is often of the O-alkyl rather than the O-alkenyl form, but the reverse tends to be true in heart lipids. In animal tissues, the alkyl and alkenyl moieties in both non-polar and phospholipids tend to be rather simple in composition with 16:0, 18:0 and 18:1 (double bond in position 9) predominating. Ether analogues of triacylglycerols, i.e. 1-alkyldiacyl-sn-glycerols, are present at trace levels only if at all in most animal tissues, but they can be major components of some marine lipids. [HMDB]

CAS Number

Not Available

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
1-O-Octadecyl-sn-glycero-3-ocholine	ChEBI
1-O-Octadecyl-sn-glycero-3-phosphocholine	HMDB
1-O-Octadecyl-sn-glyceryl-3-phosphorylcholine	HMDB
1-O-Octadecylglycerol-3-atidylcholine	ChEBI
1-O-Octadecylglycerol-3-phosphatidylcholine	HMDB
1-Octadecyl-GPC	HMDB
1-Octadecyl-lysophosphatidylcholine	HMDB
1-Octadecyl-sn-glycero-3-ocholine	ChEBI
1-Octadecyl-sn-glycero-3-phosphocholine	HMDB
1-Octadecylglycero-3-phosphocholine	HMDB

Showing 1 to 10 of 37 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00027 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.46	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.05 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	151.72 m³·mol⁻¹	ChemAxon
Polarizability	62.7 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

Chemical Formula

C26H56NO6P

IUPAC name

(2-{[(2R)-2-hydroxy-3-(octadecyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

InChI Identifier

InChI=1S/C26H56NO6P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-22-31-24-26(28)25-33-34(29,30)32-23-21-27(2,3)4/h26,28H,5-25H2,1-4H3/t26-/m1/s1

InChI Key

XKBJVQHMEXMFDZ-AREMUKBSSA-N

Isomeric SMILES

[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

Average Molecular Weight

509.6997

Monoisotopic Molecular Weight

509.384525041

Classification

Description

Belongs to the class of organic compounds known as monoalkylglycerophosphocholines. Monoalkylglycerophosphocholines are compounds containing glycerophosphocholine moiety attached to an fatty acyl chain through an ether bond.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Monoalkylglycerophosphocholines

Alternative Parents

Substituents

Monoalkylglycerophosphocholine
Phosphocholine
Glycerol ether
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Quaternary ammonium salt
Tetraalkylammonium salt
Secondary alcohol
Ether
Dialkyl ether
Hydrocarbon derivative
Alcohol
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Organic salt
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

organic molecular entity (CHEBI:75216 )
1-alkyl-sn-glycero-3-phosphocholine (CHEBI:75216 )
Monoalkylglycerophosphocholines (LMGP01060014 )

Ontology

Physiological effect

Organoleptic effect:

Touch:

Smooth

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Blood

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	LysoPC(O-18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-5930000000-c002f9346ff27ec388a3	Spectrum
Predicted GC-MS	LysoPC(O-18:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9460000000-f8bf856a15fd2cd2fa22	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-9123230000-9e5018d60ea3b2b28b32	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ugr-9455200000-0c72dc03f55ca1a4599e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-9231000000-adbce76401a5b20f74d5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0010490000-78228db3f0e06f9d298c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ar0-2160920000-56a3704799b8868294e2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-9280000000-a127711d12f38e903413	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000090000-92389686f000bb55e113	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000090000-92389686f000bb55e113	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-0000930000-3fa7cb0f3d40c52c6b6a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000090000-0092c5cfc59f1e835b62	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0020290000-1cacf188cd006762529a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210100000-3e2f6987fc891e79e2c0	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000090000-ac3949a1bc7527be80e6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0110690000-b1a4faf5ff77d30fbafc	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-0110910000-2f268286db3bc04e9cec	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0il0-1900160000-4dc04f9d727b989bed34	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ik9-1710190000-87893f3898856e238ceb	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ik9-0710190000-487f87885e45a61ac64d	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB11149

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
60 kDa lysophospholipase	ASPG	Q86U10
Eosinophil lysophospholipase	CLC	Q05315
Lysophosphatidylcholine acyltransferase 2	LPCAT2	Q7L5N7
Lysophospholipid acyltransferase 5	LPCAT3	Q6P1A2
Platelet-activating factor acetylhydrolase	PLA2G7	Q13093
Platelet-activating factor acetylhydrolase 2, cytoplasmic	PAFAH2	Q99487
Platelet-activating factor acetylhydrolase IB subunit beta	PAFAH1B2	P68402
Platelet-activating factor acetylhydrolase IB subunit gamma	PAFAH1B3	Q15102