Livestock Metabolome Database: Showing metabocard for LysoPC(16:1(9Z)) (LMDB00527)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:50 UTC

Update Date

2021-04-30 20:57:43 UTC

Lmdb

LMDB00527

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(16:1(9Z))

Description

LysoPC(16:1(9Z)) 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(16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position. The palmitoleic acid moiety is derived from animal fats and vegetable 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-Hexadecenoyl)-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoleoyl-glycero-3-phosphocholine	ChEBI
1-Palmitoleoyl-glycerophosphocholine	ChEBI
1-Palmitoleoyl-GPC	ChEBI
GPC(16:1(9Z))	ChEBI
GPC(16:1)	ChEBI
LPC 16:1(9Z)/0:0	ChEBI
LPC(16:1(9Z)/0:0)	ChEBI
LysoPC 16:1(9Z)/0:0	ChEBI
Lysophosphatidylcholine(16:1(9Z)/0:0)	ChEBI
PC 16:1(9Z)/0:0	ChEBI
PC(16:1(9Z)/0:0)	ChEBI
LPC(16:1)	HMDB
LPC(16:1/0:0)	HMDB
LPC(16:1n7/0:0)	HMDB
LPC(16:1W7/0:0)	HMDB
LyPC(16:1)	HMDB
LyPC(16:1/0:0)	HMDB
LyPC(16:1n7/0:0)	HMDB
LyPC(16:1W7/0:0)	HMDB
LysoPC a C16:1	HMDB
LysoPC(16:1)	HMDB
LysoPC(16:1/0:0)	HMDB
LysoPC(16:1n7/0:0)	HMDB
LysoPC(16:1W7/0:0)	HMDB
Lysophosphatidylcholine(16:1)	HMDB
Lysophosphatidylcholine(16:1/0:0)	HMDB
Lysophosphatidylcholine(16:1n7/0:0)	HMDB
Lysophosphatidylcholine(16:1W7/0:0)	HMDB
LysoPC(16:1(9Z))	HMDB
1-(9Z-Hexadecenoyl)-glycero-3-phosphocholine	HMDB
1-Palmitoleoylglycerophosphocholine	HMDB
1-Palmitoleoyl-lysophosphatidylcholine	HMDB
1-Palmitoleoyl-sn-glycero-3-phosphocholine	HMDB
GPC(16:1(9Z)/0:0)	HMDB
GPC(16:1n7)	HMDB
GPC(16:1n7/0:0)	HMDB
GPC(16:1W7)	HMDB
GPC(16:1W7/0:0)	HMDB
LPC(16:1(9Z))	HMDB
LPC(16:1n7)	HMDB
LPC(16:1W7)	HMDB
LysoPC(16:1n7)	HMDB
LysoPC(16:1W7)	HMDB
Lysophosphatidylcholine(16:1(9Z))	HMDB
Lysophosphatidylcholine(16:1n7)	HMDB
Lysophosphatidylcholine(16:1W7)	HMDB
LysoPC(16:1(9Z)/0:0)	ChEBI

Chemical Formula

C₂₄H₄₈NO₇P

Average Molecular Weight

493.6142

Monoisotopic Molecular Weight

493.316839407

IUPAC Name

(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h10-11,23,26H,5-9,12-22H2,1-4H3/b11-10-/t23-/m1/s1

InChI Key

LFUDDCMNKWEORN-ZXEGGCGDSA-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:73851 )
lysophosphatidylcholine 16:1 (CHEBI:73851 )
Monoacylglycerophosphocholines (LMGP01050022 )

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	1.72	ALOGPS
logP	0.83	ChemAxon
logS	-6.1	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	23	ChemAxon
Refractivity	143.39 m³·mol⁻¹	ChemAxon
Polarizability	56.45 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	splash10-009i-9421000000-8369cf40512bb91f9a92	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000190000-3b2f823b3cd8feb26a69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udo-0002990000-7176cdf7186de27b5716	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0j4l-0309300000-27e1bde7aced3e495eaf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0000900000-20d8b47f384d6c6abc9d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0900600000-d81e90dde6012dc43928	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-0910400000-7b25c82c4a89b9527428	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0030900000-f418d5b39662ed44b8b0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1090100000-eb1b8f27f35b0db065ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1090000000-e8497356b3a95210d3f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000190000-d207603b0418f8cc497d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-0090070000-848973b728ef1ffc0d69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090020000-121fe6e93b0d8bcfe171	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000190000-fa3d2231e19f49a461ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-0001960000-6bdc0b97b839b55840ee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pcr-1609710000-c34b47c99b7f3709e023	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

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	Porcine	Sergio Polakof, D...	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 but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Plasma	Detected and Quantified	0.8792 +/- 0.1030-0.9604+/-0.1030 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	1.1179 +/- 0.0950-0.9821+/-0.0950 uM	Not Available	Porcine	22492530	details
Proximal colon	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Ruminal Fluid	Detected and Quantified	0.16 +/- 0.04 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	2.2058 +/- 0.8559 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.5071 +/- 0.9657 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.0679 +/- 0.6814 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.3073 +/- 0.5866 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.4355 +/- 0.7845 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.447 +/- 1.3102 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.5284 +/- 0.815 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.86 +/- 1.39 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	2.2528 +/- 0.7153 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.4516 +/- 0.9791 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.5177 +/- 0.8494 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.2703 +/- 0.7932 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.8362 +/- 0.6583 uM	Normal	Ovine	Goldansaz et al.,...	details