Livestock Metabolome Database: Showing metabocard for LysoPC(18:2(9Z,12Z)) (LMDB00530)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:54 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00530

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(18:2(9Z,12Z))

Description

LysoPC(18:2(9Z,12Z)) 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(18:2(9Z,12Z)), in particular, consists of one chain of linoleic acid at the C-1 position. The linoleic acid moiety is derived from seed oils. 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
1-(9Z,12Z)-Octadecadienoyl-sn-glycero-3-phosphocholine	ChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphocholine	ChEBI
1-(9Z,12Z-Octadecadienoyl)-sn-glycero-3-phosphocholine	ChEBI
1-18:2-LysoPC	ChEBI
1-Linoleoyl-glycero-3-phosphocholine	ChEBI
1-Linoleoyl-GPC	ChEBI
1-Linoleoyl-GPC (18:2)	ChEBI
1-Linoleoylglycerophosphocholine	ChEBI
GPC(18:2)	ChEBI
GPC(18:2/0:0)	ChEBI
LPC 18:2(9Z,12Z)/0:0	ChEBI
LPC(18:2)	ChEBI
LPC(18:2/0:0)	ChEBI
LPC(18:2n6/0:0)	ChEBI
LPC(18:2Omega6/0:0)	ChEBI
LyPC(18:2)	ChEBI
LyPC(18:2n6/0:0)	ChEBI
LyPC(18:2omega6/0:0)	ChEBI
LysoPC 18:2(9Z,12Z)/0:0	ChEBI
LysoPC(18:2)	ChEBI
LysoPC(18:2/0:0)	ChEBI
LysoPC(18:2n6/0:0)	ChEBI
LysoPC(18:2omega6/0:0)	ChEBI
Lysophosphatidylcholine(18:2(9Z,12Z)/0:0)	ChEBI
Lysophosphatidylcholine(18:2)	ChEBI
Lysophosphatidylcholine(18:2/0:0)	ChEBI
Lysophosphatidylcholine(18:2n6/0:0)	ChEBI
Lysophosphatidylcholine(18:2omega6/0:0)	ChEBI
PC 18:2(9Z,12Z)/0:0	ChEBI
PC(18:2(9Z,12Z)/0:0)	ChEBI
LyPC(18:2/0:0)	HMDB
LysoPC(18:2(9Z,12Z))	HMDB
1-Linoleoyl lysolecithin	HMDB
1-Linoleoyl-sn-glycero-3-phosphorylcholine	HMDB
1-Linoleoylglycerol-3-phosphorylcholine	HMDB
1-Linoleoylphosphatidylcholine	HMDB
Linoleoyllysolecithin	HMDB
Linoleyl lysophosphatidylcholine	HMDB
Lysophosphatidylcholine 18:2	HMDB
1-Linoleoyl-lysophosphatidylcholine	HMDB
1-Linoleoyl-sn-glycero-3-phosphocholine	HMDB
GPC(18:2(9Z,12Z))	HMDB
GPC(18:2(9Z,12Z)/0:0)	HMDB
GPC(18:2n6)	HMDB
GPC(18:2n6/0:0)	HMDB
GPC(18:2W6)	HMDB
GPC(18:2W6/0:0)	HMDB
LPC(18:2(9Z,12Z))	HMDB
LPC(18:2(9Z,12Z)/0:0)	HMDB
LPC(18:2n6)	HMDB
LPC(18:2W6)	HMDB
LPC(18:2W6/0:0)	HMDB
LysoPC(18:2n6)	HMDB
LysoPC(18:2W6)	HMDB
LysoPC(18:2W6/0:0)	HMDB
Lysophosphatidylcholine(18:2(9Z,12Z))	HMDB
Lysophosphatidylcholine(18:2n6)	HMDB
Lysophosphatidylcholine(18:2W6)	HMDB
Lysophosphatidylcholine(18:2W6/0:0)	HMDB
LysoPC(18:2(9Z,12Z)/0:0)	ChEBI

Chemical Formula

C₂₆H₅₀NO₇P

Average Molecular Weight

519.6515

Monoisotopic Molecular Weight

519.332489471

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C26H50NO7P/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/h9-10,12-13,25,28H,5-8,11,14-24H2,1-4H3/b10-9-,13-12-/t25-/m1/s1

InChI Key

SPJFYYJXNPEZDW-FTJOPAKQSA-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:28733 )
lysophosphatidylcholine 18:2 (CHEBI:28733 )
Monoacylglycerophosphocholines (LMGP01050035 )

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	2.22	ALOGPS
logP	1.36	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	105.12 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	153.71 m³·mol⁻¹	ChemAxon
Polarizability	58.75 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	splash10-03kl-9431010000-c20360afbdedc9d9232f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000190000-3c86eb832bb0e5b457ff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0190-0002990000-61bb2de3bf360b7c5784	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0frl-0309400000-703f583c1dec34d85363	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0000090000-971f1431e3c2228b9f5d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-0900060000-dd4dca9634d21e863fe4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0910040000-75b3d9cd99357a630043	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0030090000-9b4f9f161f1e634d70b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-1090010000-2378656ce1b1501e42df	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-1090000000-ed0e0c463537d6bd8f93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000190000-85bff21ad2f9c91a7447	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0001960000-38c8f8d665d29a310286	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pcr-1609710000-e08a75389116b197e774	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000090000-7d81a037787f63d95855	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0090070000-6e0343e152dc3c713a98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0090020000-20568d21d5462d55a6c0	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	Bovine	20647382	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	25913299	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected and Quantified	13.2 +/- 2.46 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	4.31 +/- 2.3 uM	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.08 +/- 0.02 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	13.5179 +/- 4.7448 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.1609 +/- 7.2675 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	17.7431 +/- 5.0615 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.877 +/- 6.4777 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.2537 +/- 6.967 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details
Serum	Detected and Quantified	17.99 +/- 6.4984 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.458 +/- 10.9227 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.1947 +/- 8.0135 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	18.39 +/- 9.03 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	16.0937 +/- 4.8211 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.7666 +/- 6.1074 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	16.7463 +/- 5.445 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	17.7019 +/- 4.679 uM	Normal	Ovine	Goldansaz et al.,...	details