Livestock Metabolome Database: Showing metabocard for LysoPC(16:0) (LMDB00526)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:49 UTC

Update Date

2021-04-30 20:57:43 UTC

Lmdb

LMDB00526

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(16:0)

Description

LysoPC(16:0) 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(16:0), in particular, consists of one chain of palmitic acid at the C-1 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphate	ChEBI
1-16:0-LysoPC	ChEBI
1-16:0-Lysophosphatidylcholine	ChEBI
1-Hexadecanoyl-2-lysophosphatidylcholine	ChEBI
1-Palmitoyl-2-hydroxy-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoyl-2-lysophosphatidylcholine	ChEBI
1-Palmitoyl-GPC	ChEBI
1-Palmitoyl-GPC (16:0)	ChEBI
1-Palmitoyl-phosphatidylcholine	ChEBI
1-Palmitoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoylphosphatidylcholine	ChEBI
16:0 LYSO-PC	ChEBI
GPC(16:0)	ChEBI
GPC(16:0/0:0)	ChEBI
GPCho 16:0/0:0	ChEBI
GPCho(16:0/0:0)	ChEBI
LPC 16:0/0:0	ChEBI
LPC(16:0)	ChEBI
LPC(16:0/0:0)	ChEBI
LyPC(16:0)	ChEBI
LyPC(16:0/0:0)	ChEBI
LysoPC 16:0/0:0	ChEBI
LysoPC(16:0)	ChEBI
Lysophosphatidylcholine(16:0)	ChEBI
Lysophosphatidylcholine(16:0/0:0)	ChEBI
PC(16:0/0:0)	ChEBI
(2R)-2-Hydroxy-3-(hexadecanoyloxy)propyl 2-(trimethylazaniumyl)ethyl phosphoric acid	Generator
1-Palmitoyl-glycero-3-phosphocholine	HMDB
1-Palmitoyl-lysophosphatidylcholine	HMDB
LysoPC a C16:0	HMDB
1-Pam-2-lysoptdcho	HMDB
1-Hexadecanoyl-glycero-3-phosphocholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Palmitoylglycerol-3-phosphorylcholine	HMDB
Hydroxide inner salt(S)-isomer OF we 201	HMDB
1-O-Hexadecylpropanediol 3-phosphorylcholine	HMDB
1-Palmitoyllysophosphatidylcholine	HMDB
LYSO-PC	HMDB
Hydroxide inner salt(R)-isomer OF we 201	HMDB
Hydroxide inner salt(+-)-isomer OF we 201	HMDB
Palmitoyl lysophosphatidylcholine	HMDB
1-Hexadecanoylglycerophosphocholine	HMDB
1-Palmitoylglycerophosphocholine	HMDB
1-Hexadecanoyl-sn-glycero-3-phosphocholine	HMDB
1-Hexadecanoyl-sn-glycerol-3-phosphorylcholine	HMDB
1-Hexadecanoyllysolecithin	HMDB
1-Hexadecyl-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-sn-glycero-3-phosphocholine	HMDB
1-O-Palmitoyl-sn-glyceryl-3-phosphorylcholine	HMDB
1-Palmitoyl-2-lyso-sn-glycero-3-phosphocholine	HMDB
1-Palmitoyl-L-alpha-lysophosphatidylcholine	HMDB
1-Palmitoyl-L-α-lysophosphatidylcholine	HMDB
1-Palmitoyl-sn-glycero-3-phosphorylcholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphatidylcholine	HMDB
1-Palmitoyl-sn-glycerol-3-phosphocholine	HMDB
1-Palmitoyllecithin	HMDB
C(16)-Lysophosphatidylcholine	HMDB
L-Palmitoyllysolecithin	HMDB
L-alpha-Lysopalmitoylphosphatidylcholine	HMDB
L-alpha-Palmitoyllysophosphatidylcholine	HMDB
L-Α-lysopalmitoylphosphatidylcholine	HMDB
L-Α-palmitoyllysophosphatidylcholine	HMDB
Lysophosphatidylcholine C16:0	HMDB
MPPC	HMDB
Palmitoyl L-alpha-lysolecithin	HMDB
Palmitoyl L-alpha-lysophosphatidylcholine	HMDB
Palmitoyl L-lysophosphatidylcholine	HMDB
Palmitoyl L-α-lysolecithin	HMDB
Palmitoyl L-α-lysophosphatidylcholine	HMDB
gamma-Palmitoyl-L-alpha-lysophosphatidylcholine	HMDB
Γ-palmitoyl-L-α-lysophosphatidylcholine	HMDB
1-Hexadecanoyl-3-glycerophosphorylcholine	HMDB
1-Palmitoyl-3-glycerylphosphorylcholine	HMDB
1-Palmitoyllysolecithin	HMDB
Palmitoyllysolecithin	HMDB
Palmitoyllysophosphatidyl choline	HMDB
LysoPC(16:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₄H₅₀NO₇P

Average Molecular Weight

495.6301

Monoisotopic Molecular Weight

495.332489471

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-hydroxypropyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C24H50NO7P/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/h23,26H,5-22H2,1-4H3/t23-/m1/s1

InChI Key

ASWBNKHCZGQVJV-HSZRJFAPSA-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

lysophosphatidylcholine 16:0 (CHEBI:72998 )
Monoacylglycerophosphocholines (LMGP01050018 )

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	1.83	ALOGPS
logP	1.19	ChemAxon
logS	-6.2	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	142.27 m³·mol⁻¹	ChemAxon
Polarizability	58.03 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	splash10-01y9-9311000000-9632c8a0304eb91f3751	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
LC-MS/MS	LC-MS/MS Spectrum - n/a 1V, negative	splash10-001i-0010960000-db67de4509c75d7797d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-014i-0100190000-466a257c45e674564cc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-014i-0300490000-fd86cfc8580fd230b8a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-1000-1900860000-1a2c5a54bd973898558d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0zfr-2901600000-7c35aada431d2e867652	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0udi-5901100000-be073d1065c18511ab41	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 1V, positive	splash10-0002-0300900000-849ef7d9847d865ee542	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 3V, positive	splash10-0002-0000900000-bd89b3b43b9782d3e5d0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 4V, positive	splash10-0002-0000900000-7c8338b951da28a32df8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 5V, positive	splash10-0002-0000900000-aa4c98d730731747150c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 7V, positive	splash10-0002-0000900000-2d0497b2b78955e2f373	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, positive	splash10-0002-0100900000-864a738c4e243f3650a8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-0002-0400900000-ce5450f53d5acc84a31e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, positive	splash10-000t-0700900000-4ea431cd2258d012bb04	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-0f8a-0900400000-584dbb5e4958e61bcab8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, positive	splash10-0f89-0900200000-2b522394881a967d30af	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, positive	splash10-0f89-0900100000-64234f354a55048175bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, positive	splash10-0f89-0900000000-5f827a15f6679c860460	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-0f89-1900000000-f09c6fb5cf772c643504	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, positive	splash10-0f89-1900000000-d5bef12c7df660f031a9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, positive	splash10-0f89-1900000000-f069c0af6b2eb74b9336	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, positive	splash10-0f89-3900000000-d43ab983a88913d21991	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, positive	splash10-0f8i-5900000000-2b2fa2819f5e2fce5fe4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 13V, positive	splash10-0002-0000900000-0b99348189a68c7f5592	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, positive	splash10-0002-0300900000-4249906ba39f9c0a48ea	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

Milk
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Milk	Detected but not Quantified	Not Applicable	Not Available	Bovine	1779072	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	22612070	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Serum	Detected and Quantified	34.4745 +/- 14.1395 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	34.6537 +/- 9.4709 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details
Serum	Detected and Quantified	37.106 +/- 18.3048 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.7593 +/- 10.0073 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.4895 +/- 8.1087 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.693 +/- 16.9546 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.2431 +/- 12.2896 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	54.91 +/- 27.42 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	35.6261 +/- 17.3817 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	34.4975 +/- 13.1181 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	35.1456 +/- 10.4328 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	32.7641 +/- 6.3431 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	31.7083 +/- 10.3863 uM	Normal	Ovine	Goldansaz et al.,...	details