Livestock Metabolome Database: Showing metabocard for LysoPC(17:0) (LMDB00571)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:47 UTC

Update Date

2021-04-30 20:57:43 UTC

Lmdb

LMDB00571

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(17:0)

Description

LysoPC(17:0) 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(17:0), in particular, consists of one chain of margaric acid at the C-1 position. The margaric acid moiety is derived from butter, milk and fat of ruminants. 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-Heptadecanoyl-glycero-3-phosphocholine	ChEBI
1-Margaroyl-GPC	ChEBI
1-Margaroyl-GPC (17:0)	ChEBI
GPC(17:0)	ChEBI
LPC (17:0/0:0)	ChEBI
LPC 17:0/0:0	ChEBI
LPC(17:0/0:0)	ChEBI
LysoPC 17:0/0:0	ChEBI
Lysophosphatidylcholine(17:0)	ChEBI
Lysophosphatidylcholine(17:0/0:0)	ChEBI
PC 17:0/0:0	ChEBI
PC(17:0/0:0)	ChEBI
LPC(17:0)	HMDB
LyPC(17:0)	HMDB
LyPC(17:0/0:0)	HMDB
LysoPC a C17:0	HMDB
1-Margaroyl-glycero-3-phosphocholine	HMDB
LysoPC(17:0)	HMDB
1-Heptadecanoyl-2-hydroxy-sn-glycero-3-phosphocholine	HMDB
1-Heptadecanoylglycerophosphocholine	HMDB
Lysophosphatidylcholine (C17:0)	HMDB
1-Margaroylglycerophosphocholine	HMDB
1-Margaroyl-lysophosphatidylcholine	HMDB
1-Margaroyl-sn-glycero-3-phosphocholine	HMDB
GPC(17:0/0:0)	HMDB
LysoPC(17:0/0:0)	Lipid Annotator, ChEBI

Chemical Formula

C₂₅H₅₂NO₇P

Average Molecular Weight

509.6566

Monoisotopic Molecular Weight

509.348139535

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C25H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-25(28)31-22-24(27)23-33-34(29,30)32-21-20-26(2,3)4/h24,27H,5-23H2,1-4H3/t24-/m1/s1

InChI Key

SRRQPVVYXBTRQK-XMMPIXPASA-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 17:0 (CHEBI:74340 )
Monoacylglycerophosphocholines (LMGP01050024 )

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	2.18	ALOGPS
logP	1.64	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	146.87 m³·mol⁻¹	ChemAxon
Polarizability	60.02 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	splash10-00g0-9311000000-93a0b5b9e5f537c618dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900000000-5f02fa0f1176a59f106e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000090000-94d9e2275cda76286a6c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0200090000-34355ed9a9a5b146b7cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000190000-d912ebcc582e7e7ebf68	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014l-0090070000-1ba0f9762e33fbcce22b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0090020000-08553871ff6c127650b2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000190000-fd17df396eea86beaebc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0001960000-25105e7a20be144cd00d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fdk-1609710000-6761294dff05eef577b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0030090000-b1470a5e8c1f72620b13	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0090010000-9b7a3651bf4a9dca6929	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-0090000000-f25c5da4f67ced9e0d09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0100690000-8067aca90102c943040e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01q9-0900150000-710bcf758d5d5c216653	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f8c-0910300000-fb1151d78a4fed481d67	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000190000-4a106fa491faee412eb8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0b90-0002990000-99899b56168cb2071f72	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ke9-0309400000-2332b4fc27fe465cb173	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	Bovine	24630653	details
Plasma	Detected but not Quantified	Not Applicable	Not Available	Porcine	24624922	details
Serum	Detected and Quantified	2.9404 +/- 1.26 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.1057 +/- 1.336 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3169 +/- 1.0497 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5295 +/- 2.0251 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.8236 +/- 1.1386 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.0954 +/- 0.7084 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3152 +/- 1.5737 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.211 +/- 1.3747 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	5.88 +/- 2.81 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details
Serum	Detected and Quantified	3.3358 +/- 1.7887 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.238 +/- 1.1673 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2681 +/- 1.0895 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	2.9277 +/- 0.75 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0012108

FooDB ID

FDB028772

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

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for LysoPC(17:0) (LMDB00571)

Structure for LMDB00571 (LysoPC(17:0))