Livestock Metabolome Database: Showing metabocard for LysoPC(18:1(11Z)) (LMDB00529)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:53 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00529

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(18:1(11Z))

Description

LysoPC(18:1(11Z)) 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(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. 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-Vaccenoyl-glycero-3-phosphocholine	ChEBI
LPC(18:1)	ChEBI
LysoPC(18:1(11Z))	ChEBI
LysoPC(18:1)	ChEBI
Lysophosphatidylcholine(18:1)	ChEBI
PC 18:1(11Z)/0:0	ChEBI
PC(18:1(11Z)/0:0)	ChEBI
LPC(18:1/0:0)	HMDB
LPC(18:1n7/0:0)	HMDB
LPC(18:1W7/0:0)	HMDB
LyPC(18:1)	HMDB
LyPC(18:1/0:0)	HMDB
LyPC(18:1n7/0:0)	HMDB
LyPC(18:1W7/0:0)	HMDB
LysoPC a C18:1	HMDB
LysoPC(18:1/0:0)	HMDB
LysoPC(18:1n7/0:0)	HMDB
LysoPC(18:1W7/0:0)	HMDB
Lysophosphatidylcholine(18:1/0:0)	HMDB
Lysophosphatidylcholine(18:1n7/0:0)	HMDB
Lysophosphatidylcholine(18:1W7/0:0)	HMDB
1-(11Z-Octadecenoyl)-glycero-3-phosphocholine	HMDB
1-Vaccenoylglycerophosphocholine	HMDB

Chemical Formula

C₂₆H₅₂NO₇P

Average Molecular Weight

521.6673

Monoisotopic Molecular Weight

521.348139535

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C26H52NO7P/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/h10-11,25,28H,5-9,12-24H2,1-4H3/b11-10-/t25-/m1/s1

InChI Key

PZRFVAHZNWPPAC-VBKSFVIKSA-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:86255 )
lysophosphatidylcholine 18:1 (CHEBI:86255 )

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	2.38	ALOGPS
logP	1.72	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	25	ChemAxon
Refractivity	152.59 m³·mol⁻¹	ChemAxon
Polarizability	60.46 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	splash10-007t-5950100000-d2d627f1bf5f98609109	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-024u-9431010000-e487b14464af3dc739a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9162130000-aa9b8b51c78b1b8d1753	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-8393000000-14b298ea6483402da89f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9140000000-fbca67ff1ab00ebfc5bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01x0-0090030000-706190fb31fd956d11ed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0090100000-6d76540b1efe6814b7b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01si-5190000000-95de222a575d1763b1f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000190000-37dcc74901c1425d0392	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0190-0002990000-c8110d0a5e4476020596	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0frj-0309400000-cd464845573077fb0e9f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0030090000-c08a294df5c170ac8b76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1090010000-3f3fbc869926a73a5b72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090000000-1894b105723e28dacec8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000090000-f6a072a97b578a3bd0b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-0090070000-f56fc89aebf13639f1ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090020000-be75beb7bf742731dc1e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000190000-ed1ce66db5beed8bfab7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0001960000-b2d5105862a37356da93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gw0-1609710000-4adbedbb1f89568d7285	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0000090000-382efaabb1329b98f1ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-0900060000-7d4d5ee776e7a08537ae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0910040000-b15364334c9b09b73db5	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Bile acid
Brain cortex
Jejunum
Liver
Pancreas
Plasma
Proximal colon
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Brain cortex	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Jejunum	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Liver	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Pancreas	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	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	23805856	details
Proximal colon	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.04 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	18.14 +/- 3.7604 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.6219 +/- 7.473 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	20.1844 +/- 5.2701 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details
Serum	Detected and Quantified	20.1525 +/- 6.1983 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.0394 +/- 5.6334 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.0492 +/- 5.9961 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.1895 +/- 10.7443 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	21.6015 +/- 7.4224 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.501 +/- 5.7893 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.2946 +/- 6.8847 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	20.3455 +/- 5.0023 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	19.8607 +/- 5.2048 uM	Normal	Ovine	Goldansaz et al.,...	details