Showing Compound LPC(0:0/18:0) (FDB027907)

Record Information

Version

1.0

Creation date

2011-09-21 01:31:47 UTC

Update date

2018-05-28 18:37:58 UTC

Primary ID

FDB027907

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

LPC(0:0/18:0)

Description

LysoPC(0:0/18:0) or LPC(0:0/18:0) is a lysophospholipid (LPL). LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. LysoPC(0:0/18:0) has been shown to be protective against lethal sepsis in experimental animals by various mechanisms, including stimulation of neutrophils to eliminate invading pathogens through a peroxide-dependent reaction. [HMDB]

CAS Number

4421-58-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl ate	ChEBI
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl ic acid	Generator
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	HMDB
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	HMDB
1-Hydroxy-2-octadecanoyl-sn-glycero-3-ocholine	HMDB
1-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphocholine	HMDB
1-Hydroxy-2-Octadecanoyl-sn-glycero-3-phosphocholine	hmdb
1-Hydroxy-2-stearoyl-sn-glycero-3-ocholine	HMDB
1-Hydroxy-2-stearoyl-sn-glycero-3-phosphocholine	HMDB
1-Stearoyllysophosphatidylcholine	manual

Showing 1 to 10 of 34 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.00022 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.08	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	151.48 m³·mol⁻¹	ChemAxon
Polarizability	62.33 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

C26H54NO7P

IUPAC name

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

InChI Identifier

InChI=1S/C26H54NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)34-25(23-28)24-33-35(30,31)32-22-21-27(2,3)4/h25,28H,5-24H2,1-4H3/t25-/m1/s1

InChI Key

IQGPMZRCLCCXAG-RUZDIDTESA-N

Isomeric SMILES

[H][C@@](CO)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC

Average Molecular Weight

523.6832

Monoisotopic Molecular Weight

523.363789599

Classification

Description

Belongs to the class of organic compounds known as 2-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-2 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

2-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

2-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Primary alcohol
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-acyl-sn-glycero-3-phosphocholine (CHEBI:76076 )
lysophosphatidylcholine 18:0 (CHEBI:76076 )
Monoacylglycerophosphocholines (LMGP01050076 )

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	LPC(0:0/18:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fek-9550100000-80d62412107a36847bc7	Spectrum
Predicted GC-MS	LPC(0:0/18:0), 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-008a-9721020000-9b41f1bf1e3d5e7cf26c	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fc0-0900060000-e99379bc4ac53cc77147	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ul0-0900050000-23f28f5f047f20928b27	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ul0-0900050000-bfd773fc6fa74017c0dc	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9071130000-2c3354f59d1c3ced0f44	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n3-8292010000-d0e88a09c384d49429af	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-9130000000-de498d2cd72d4ce9e8ba	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0070290000-bdddd2700d06c482f6d8	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-2370920000-8d3fcd824e1c0856f606	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o0-6290000000-dabf6a0ad90d8af67ae6	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1100090000-3808cd3b9510a0dec128	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2910020000-6397418d2fe7e18b74e4	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-b110314336110b417795	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000090000-c3d13afe335d8b212b66	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-0090160000-c2b2361f52a0743ec66a	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-8290200000-f73f39a5b22cf648489f	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

24766523

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

24779491

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB11128

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