Livestock Metabolome Database: Showing metabocard for LysoPC(18:0) (LMDB00528)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:52 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00528

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(18:0)

Description

LysoPC(18:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:0), in particular, consists of one chain of stearic acid at the C-1 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil. 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. In blood plasma significant amounts of lysophosphatidylcholine are formed by a specific enzyme system, lecithin:cholesterol acyltransferase (LCAT), which is secreted from the liver. The enzyme catalyzes the transfer of the fatty acids of position sn-2 of phosphatidylcholine to the free cholesterol in plasma, with formation of cholesterol esters and lysophosphatidylcholine. Lysophospholipids have a role in lipid signaling by acting on lysophospholipid receptors (LPL-R). LPL-R's are members of the G protein-coupled receptor family of integral membrane proteins.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
1-O-Stearoyl-sn-glycero-3-phosphocholine	ChEBI
1-Octadecanoyl-sn-glycero-3-phosphocholine	ChEBI
1-Stearoyl-glycero-3-phosphocholine	ChEBI
1-Stearoylglycerophosphocholine (18:0)	ChEBI
1-Stearoylglycerophosphocholine(18:0)	ChEBI
18:0 LYSO-PC	ChEBI
GPCho 18:0/0:0	ChEBI
GPCho(18:0/0:0)	ChEBI
LPC 18:0/0:0	ChEBI
LPC(18:0)	ChEBI
LPC(18:0/0:0)	ChEBI
LysoPC 18:0/0:0	ChEBI
LysoPC(18:0)	ChEBI
Lysophosphatidylcholine (18:0/0:0)	ChEBI
Lysophosphatidylcholine(18:0)	ChEBI
Lysophosphatidylcholine(18:0/0:0)	ChEBI
PC 18:0/0:0	ChEBI
PC(18:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(stearoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
LyPC(18:0)	HMDB
LyPC(18:0/0:0)	HMDB
LysoPC a C18:0	HMDB
Stearoyl alpha-lysolecithin	HMDB
Stearoyllysophosphatidylcholine	HMDB
1-Octadecyl-glycero-3-phosphocholine	HMDB
1-Stearoyl-sn-glycero-3-phosphorylcholine	HMDB
Stearoyl L-alpha-lysolecithin	HMDB
1-Stearoyl-2-hydroxy-sn-glycero-3-phosphocholine	HMDB
Stearoyl alpha-lysolecithin, (+-)-isomer	HMDB
Stearoyl alpha-lysolecithin, (R)-isomer	HMDB
1-Octadecanoyl-glycero-3-phosphocholine	HMDB
1-Octadecanoylglycerophosphocholine	HMDB
1-Octadecylglycerophosphocholine	HMDB
1-Stearoylglycerophosphocholine	HMDB
1-O-Stearoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-Octadecanoyl-3-glycerophosphorylcholine	HMDB
1-Octadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Octadecanoyllysolecithin	HMDB
1-Stearoyl-2-lysophosphatidylcholine	HMDB
1-Stearoyl-3-glycerylphosphorylcholine	HMDB
1-Stearoyl-GPC	HMDB
1-Stearoyl-lysophosphatidylcholine	HMDB
1-Stearoyl-sn-glycero-3-phosphocholine	HMDB
1-Stearoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Stearoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Stearoylglycero-3-phosphorylcholine	HMDB
1-Stearoyllysophosphatidylcholine	HMDB
GPC(18:0)	HMDB
GPC(18:0/0:0)	HMDB
Lysophosphatidylcholine C18:0	HMDB
Stearoyl L-α-lysolecithin	HMDB
Stearoyl lysolecithin	HMDB
Stearoyl lysophosphatidylcholine	HMDB
LysoPC(18:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₆H₅₄NO₇P

Average Molecular Weight

523.6832

Monoisotopic Molecular Weight

523.363789599

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

IHNKQIMGVNPMTC-RUZDIDTESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 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

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-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
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:73858 )
lysophosphatidylcholine 18:0 (CHEBI:73858 )
Monoacylglycerophosphocholines (LMGP01050026 )

Ontology

Status

Detected and 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	2.53	ALOGPS
logP	2.08	ChemAxon
logS	-6.4	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	105.12 Å²	ChemAxon
Rotatable Bond Count	26	ChemAxon
Refractivity	151.48 m³·mol⁻¹	ChemAxon
Polarizability	61.71 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 (1 TMS) - 70eV, Positive	splash10-024u-9321010000-7c4db1d8f50345253e5e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900000000-4587eca1f40127997f9a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000090000-8c56fcd29df2d9fc9c2b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0200090000-3a51011c95929ab98d63	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000190000-41c73cffe2f1aaf160f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000j-0001960000-94fcb8b8814d186b45b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gw0-1609710000-ae76bfe8f474291dc445	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0030090000-f659985c9cbbaf332a78	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090010000-01d93fd13edb0afa2e7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090000000-ca0fc5a9d32fa941ad45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000090000-3069bae6fba637487e2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-0090070000-1397c10d116d343edd9e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090020000-274c1e62706a1695b7b9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fr-0000090000-0d83963fc8d256300785	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-0900060000-23beae7a997640f05765	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kai-0910040000-b24aadea134c86d41382	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000190000-db2c4daf832d5e722111	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00f0-0002990000-f2b5b69d9cc9121b1dc6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fdp-0309400000-f08bc6aa7b631fbc521e	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24477039	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected and Quantified	13.08 +/- 1.38-13.68+/-1.38 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	13.6348 +/- 1.2911-16.5439+/-1.2911 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	14.43 +/- 1.31-20.27+/-1.31 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	15.0459 +/- 1.1981-21.0933+/-1.1981 uM	Not Available	Porcine	22492530	details
Ruminal Fluid	Detected and Quantified	0.11 +/- 0.02 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	24.2115 +/- 8.1569 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	26.5964 +/- 12.0474 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	Pengcheng Zhou, J...	details
Serum	Detected and Quantified	25.8481 +/- 7.7376 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	29.5154 +/- 15.4399 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	23.954 +/- 8.8417 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	25.5941 +/- 6.9085 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	27.9319 +/- 13.1641 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	26.7219 +/- 10.9777 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.51 +/- 17.67 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	27.3614 +/- 14.0323 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	24.5202 +/- 8.9406 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	25.9446 +/- 7.7631 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	24.0429 +/- 5.5333 uM	Normal	Ovine	Goldansaz et al.,...	details