Livestock Metabolome Database: Showing metabocard for LysoPC(0:0/18:0) (LMDB00540)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:07 UTC

Update Date

2016-07-20 21:01:55 UTC

Lmdb

LMDB00540

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(0:0/18:0)

Description

LysoPC(0:0/18:0) or LPC(0:0/18:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. 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. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling. There is also a phospholipase A1, which is able to cleave the sn-1 ester bond. Lysophosphatidylcholine has pro-inflammatory properties in vitro and it is known to be a pathological component of oxidized lipoproteins (LDL) in plasma and of atherosclerotic lesions. Recently, it has been found to have some functions in cell signalling, and specific receptors (coupled to G proteins) have been identified. It activates the specific phospholipase C that releases diacylglycerols and inositol triphosphate with resultant increases in intracellular Ca2+ and activation of protein kinase C. It also activates the mitogen-activated protein kinase in certain cell types.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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	HMDB
2-Octadecanoyl-sn-glycero-3-phosphocholine	HMDB
2-Stearoyllysophosphatidylcholine	HMDB
LPC (18:0)	HMDB
PC(0:0/18:0)	HMDB
Stearoyl lysophosphatidylcholine	HMDB
(2R)-3-Hydroxy-2-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	HMDB
1-Hydroxy-2-octadecanoyl-sn-glycero-3-phosphocholine	HMDB
1-Hydroxy-2-stearoyl-sn-glycero-3-phosphocholine	HMDB
Lysophosphatidylcholine	HMDB
2-Stearoyl-glycero-3-phosphocholine	HMDB
LysoPC(18:0)	HMDB
LPC(0:0/18:0)	HMDB
Lysophosphatidylcholine(0:0/18:0)	HMDB
LyPC(0:0/18:0)	HMDB
Lysophosphatidylcholine(18:0)	HMDB
LPC(18:0)	HMDB
LyPC(18:0)	HMDB
2-Octadecanoyl-glycero-3-phosphocholine	HMDB
2-Octadecanoylglycerophosphocholine	HMDB
2-Stearoylglycerophosphocholine	HMDB
LysoPC(0:0/18:0)	Lipid Annotator

Chemical Formula

C₂₆H₅₄NO₇P

Average Molecular Weight

523.6832

Monoisotopic Molecular Weight

523.363789599

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

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

Chemical Taxonomy

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

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fek-9550100000-80d62412107a36847bc7	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-008a-9721020000-9b41f1bf1e3d5e7cf26c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0fc0-0900060000-e99379bc4ac53cc77147	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ul0-0900050000-23f28f5f047f20928b27	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0ul0-0900050000-bfd773fc6fa74017c0dc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9071130000-2c3354f59d1c3ced0f44	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n3-8292010000-d0e88a09c384d49429af	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-9130000000-de498d2cd72d4ce9e8ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00e9-0070290000-bdddd2700d06c482f6d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-2370920000-8d3fcd824e1c0856f606	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00o0-6290000000-dabf6a0ad90d8af67ae6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-1100090000-3808cd3b9510a0dec128	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-2910020000-6397418d2fe7e18b74e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dr-6900000000-b110314336110b417795	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000090000-c3d13afe335d8b212b66	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0089-0090160000-c2b2361f52a0743ec66a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-8290200000-f73f39a5b22cf648489f	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Milk
Plasma

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	11913692	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011128

FooDB ID

FDB027907

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

24766523

ChEBI ID

76076

PubChem Compound ID

24779491

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for LysoPC(0:0/18:0) (LMDB00540)

Structure for LMDB00540 (LysoPC(0:0/18:0))