Livestock Metabolome Database: Showing metabocard for LysoPC(14:0) (LMDB00525)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:48 UTC

Update Date

2021-04-30 20:57:43 UTC

Lmdb

LMDB00525

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(14:0)

Description

LysoPC(14:0) 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(14:0), in particular, consists of one chain of myristic acid at the C-1 position. The myristic acid moiety is derived from nutmeg and butter. 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-C14:0-Lysophosphatidylcholine betaine	ChEBI
1-Myristoyl-glycero-3-phosphocholine	ChEBI
1-Myristoyl-sn-glycero-3-phosphocholine betaine	ChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine	ChEBI
1-Tetradecanoyl-sn-glycero-3-phosphocholine betaine	ChEBI
LPC(14:0)	ChEBI
LPC(14:0/0:0)	ChEBI
LyPC(14:0)	ChEBI
LyPC(14:0/0:0)	ChEBI
Lysophosphatidylcholine(14:0/0:0)	ChEBI
PC(14:0/0:0)	ChEBI
LysoPC(14:0/0:0)	Lipid Annotator, ChEBI
Lysophosphatidylcholine(14:0)	Lipid Annotator, HMDB
1-tetradecanoyl-glycero-3-phosphocholine	Lipid Annotator, HMDB
LysoPC(14:0)	Lipid Annotator, HMDB
1-Myristoylglycerophosphocholine	HMDB
1-Tetradecanoylglycerophosphocholine	HMDB
1-Myristoyl-GPC	HMDB
1-Myristoyl-lysophosphatidylcholine	HMDB
1-Myristoyl-sn-glycero-3-phosphocholine	HMDB
GPC(14:0)	HMDB
GPC(14:0/0:0)	HMDB

Chemical Formula

C₂₂H₄₆NO₇P

Average Molecular Weight

467.5769

Monoisotopic Molecular Weight

467.301189343

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C22H46NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-22(25)28-19-21(24)20-30-31(26,27)29-18-17-23(2,3)4/h21,24H,5-20H2,1-4H3/t21-/m1/s1

InChI Key

VXUOFDJKYGDUJI-OAQYLSRUSA-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:64489 )
lysophosphatidylcholine 14:0 (CHEBI:64489 )
Monoacylglycerophosphocholines (LMGP01050012 )

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	1.1	ALOGPS
logP	0.3	ChemAxon
logS	-5.8	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	22	ChemAxon
Refractivity	133.07 m³·mol⁻¹	ChemAxon
Polarizability	53.74 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	splash10-0230-9411000000-7a6b8e8fd1e0609b417e	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	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	splash10-0006-0000900000-c557e23aa67a6a68e471	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0000900000-89cc0e21e01554e310d6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pcr-1617900000-231c7760e10f0c81e04b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000390000-b1814b140293d64c3417	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0090160000-48fcbf8694eed693a211	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0090110000-c40c1368f5389cd115f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gb9-0000900000-534f405ea851fa87d3e5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00lr-0900600000-9a2a86225de12cddb6bd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0910400000-63d03888aa82a44da515	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0030900000-648928c7aa526a1c5514	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0090100000-6eecefd72f10fda6c57a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0090000000-aaa1334bcdf77ff34dd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000900000-56c0d0685c46c9ba6fe3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01i0-0010900000-50babd7089582cb56ec8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0frl-0390400000-26a01ba41c58e985ad7c	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
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	Sergio Polakof, D...	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Plasma	Detected and Quantified	3.51 +/- 2.72 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	5.62 +/- 0.39 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	2.80 +/- 0.43 uM	Not Available	Bovine	24630653	details
Plasma	Detected and Quantified	5.59 +/- 0.52 uM	Not Available	Bovine	24630653	details
Serum	Detected and Quantified	1.2477 +/- 0.4011 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.4753 +/- 0.326 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	1.1674 +/- 0.3601 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.2388 +/- 0.2776 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.4453 +/- 0.2893 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.2659 +/- 0.5337 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.3773 +/- 0.3302 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.07 +/- 0.83 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	1.2601 +/- 0.4242 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.453 +/- 0.3845 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.3589 +/- 0.35 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.2968 +/- 0.2337 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.0561 +/- 0.3631 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0010379

FooDB ID

FDB027530

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

405289

ChEBI ID

64489

PubChem Compound ID

460604

Kegg Compound ID

Not Available

YMDB ID

YMDB01175

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for LysoPC(14:0) (LMDB00525)

Structure for LMDB00525 (LysoPC(14:0))