Livestock Metabolome Database: Showing metabocard for LysoPC(20:3(5Z,8Z,11Z)) (LMDB00533)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:58 UTC

Update Date

2021-04-30 20:57:44 UTC

Lmdb

LMDB00533

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(20:3(5Z,8Z,11Z))

Description

LysoPC(20:3(5Z,8Z,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(20:3(5Z,8Z,11Z)), in particular, consists of one chain of mead acid at the C-1 position. The mead acid moiety is derived from fish oils, liver and kidney. 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-Meadoyl-glycero-3-phosphocholine	ChEBI
LPC 20:3(5Z,8Z,11Z)/0:0	ChEBI
LPC(20:3(5Z,8Z,11Z)/0:0)	ChEBI
LysoPC 20:3(5Z,8Z,11Z)/0:0	ChEBI
LysoPC(20:3(5Z,8Z,11Z)/0:0)	ChEBI
Lysophosphatidylcholine(20:3(5Z,8Z,11Z)/0:0)	ChEBI
PC 20:3(5Z,8Z,11Z)/0:0	ChEBI
PC(20:3(5Z,8Z,11Z)/0:0)	ChEBI
LyPC(20:3/0:0)	Lipid Annotator, HMDB
LysoPC(20:3(5Z,8Z,11Z))	Lipid Annotator
LPC(20:3)	Lipid Annotator, HMDB
LPC(20:3/0:0)	Lipid Annotator, HMDB
LysoPC(20:3/0:0)	Lipid Annotator, HMDB
LyPC(20:3)	Lipid Annotator, HMDB
Lysophosphatidylcholine(20:3)	Lipid Annotator, HMDB
LysoPC(20:3)	Lipid Annotator, HMDB
1-(5Z,8Z,11Z-eicosatrienoyl)-glycero-3-phosphocholine	Lipid Annotator, HMDB
Lysophosphatidylcholine(20:3/0:0)	Lipid Annotator, HMDB
LPC(20:3n9/0:0)	HMDB
LPC(20:3W9/0:0)	HMDB
LyPC(20:3n9/0:0)	HMDB
LyPC(20:3W9/0:0)	HMDB
LysoPC a C20:3	HMDB
LysoPC(20:3n9/0:0)	HMDB
LysoPC(20:3W9/0:0)	HMDB
Lysophosphatidylcholine(20:3n9/0:0)	HMDB
Lysophosphatidylcholine(20:3W9/0:0)	HMDB
1-Meadoylglycerophosphocholine	HMDB
1-Meadoyl-GPC	HMDB
1-Meadoyl-lysophosphatidylcholine	HMDB
1-Meadoyl-sn-glycero-3-phosphocholine	HMDB
GPC(20:3(5Z,8Z,11Z))	HMDB
GPC(20:3(5Z,8Z,11Z)/0:0)	HMDB
GPC(20:3)	HMDB
GPC(20:3n9)	HMDB
GPC(20:3n9/0:0)	HMDB
GPC(20:3w9)	HMDB
GPC(20:3w9/0:0)	HMDB
LPC(20:3(5Z,8Z,11Z))	HMDB
LPC(20:3n9)	HMDB
LPC(20:3w9)	HMDB
LysoPC(20:3n9)	HMDB
LysoPC(20:3w9)	HMDB
Lysophosphatidylcholine(20:3(5Z,8Z,11Z))	HMDB
Lysophosphatidylcholine(20:3n9)	HMDB
Lysophosphatidylcholine(20:3w9)	HMDB

Chemical Formula

C₂₈H₅₂NO₇P

Average Molecular Weight

545.6887

Monoisotopic Molecular Weight

545.348139535

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(5Z,8Z,11Z)-icosa-5,8,11-trienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-28(31)34-25-27(30)26-36-37(32,33)35-24-23-29(2,3)4/h12-13,15-16,18-19,27,30H,5-11,14,17,20-26H2,1-4H3/b13-12-,16-15-,19-18-/t27-/m1/s1

InChI Key

YHGXYYIGHBPDMX-BUTFDPNWSA-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 20:3 (CHEBI:74343 )
1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:74343 )

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	2.71	ALOGPS
logP	1.89	ChemAxon
logS	-6.5	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	164.03 m³·mol⁻¹	ChemAxon
Polarizability	62.22 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	splash10-008a-5970300000-11203ac6a967082567ae	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0h3l-9441001000-b7be2402e57e21e62f0f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("LysoPC(20:3(5Z,8Z,11Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9153130000-18fae725515f180cca64	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01p9-8393010000-70817453771a0e8813c0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9041000000-5e5561ac131d525769b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4u-0079170000-c78131971d03e5de90c9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4r-0059200000-7b3a58f9bbf54cc35ddc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-8289000000-83a223e29de6ecf53064	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000190000-a0ae6730d99da9a4c0a5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udo-0002990000-8cd2eede2fa4ae6a1a81	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0j4l-0309400000-92edf5aa3d34b1285d04	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-0000090000-bf7fc3df698e870dec69	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001j-0900060000-e960f0563ba251b8e278	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-0910040000-a85b3fe6a7ba7ef759c7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0003090000-5f23f15b3d1cddc86c7c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1019010000-fffab587c2a32e4aa026	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0009000000-8c3173e7b9aa94759c92	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000090000-91dea8ecfdf79e4e7a22	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a59-0009070000-4ff84ef3f56eac796f10	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0039030000-159be9a74a8e1e30d620	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000090000-2fa9e2dacbd579d98321	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-0000090000-4e0d8983cb3993c06087	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9i-1609090000-d5aa77469dc8dbc46c34	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Bile acid
Liver
Plasma
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Bile acid	Detected but not Quantified	Not Applicable	Not Available	Porcine	23805856	details
Liver	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	23805856	details
Plasma	Detected and Quantified	0.4781 +/- 0.0931-0.7126+/-0.0931 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	0.7761 +/- 0.0856-0.8002+/-0.0856 uM	Not Available	Porcine	22492530	details
Serum	Detected and Quantified	3.2549 +/- 0.3996 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4572 +/- 0.8473 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4946 +/- 0.5274 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4708 +/- 0.5622 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4925 +/- 0.6446 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.6768 +/- 0.5995 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.9256 +/- 1.8472 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5792 +/- 0.864 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	1.91 +/- 0.94 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	3.5454 +/- 0.4888 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5567 +/- 0.8286 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.421 +/- 0.5236 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4142 +/- 0.4982 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0010393

FooDB ID

Not Available

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

24766531

ChEBI ID

74343

PubChem Compound ID

53480467

Kegg Compound ID

Not Available

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(20:3(5Z,8Z,11Z)) (LMDB00533)

Structure for LMDB00533 (LysoPC(20:3(5Z,8Z,11Z)))