Livestock Metabolome Database: Showing metabocard for LysoPC(20:4(8Z,11Z,14Z,17Z)) (LMDB00936)

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

Record Information

Version

1.0

Creation Date

2016-08-01 22:02:39 UTC

Update Date

2021-04-30 20:58:25 UTC

Lmdb

LMDB00936

Secondary Accession Numbers

None

Metabolite Identification

Common Name

LysoPC(20:4(8Z,11Z,14Z,17Z))

Description

LysoPC(20:4(8Z,11Z,14Z,17Z)/0:0) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. LysoPC(20:4(8Z,11Z,14Z,17Z)/0:0), in particular, consists of one 8Z,11Z,14Z,17Z-eicosapentaenoyl chain. 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.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Eicsoatetraenoyl-glycero-3-phosphocholine	ChEBI
LPC(20:4/0:0)	ChEBI
LysoPC(20:4(8Z,11Z,14Z,17Z))	ChEBI
LysoPC(20:4/0:0)	ChEBI
Lysophosphatidylcholine(20:4/0:0)	ChEBI
1-Eicsoate	HMDB
1-Eicsoic acid	HMDB
LPC(20:4)	HMDB
LPC(20:4n3/0:0)	HMDB
LPC(20:4W3/0:0)	HMDB
LyPC(20:4)	HMDB
LyPC(20:4/0:0)	HMDB
LyPC(20:4n3/0:0)	HMDB
LyPC(20:4W3/0:0)	HMDB
LysoPC a C20:4	HMDB
LysoPC(20:4)	HMDB
LysoPC(20:4n3/0:0)	HMDB
LysoPC(20:4W3/0:0)	HMDB
Lysophosphatidylcholine(20:4)	HMDB
Lysophosphatidylcholine(20:4n3/0:0)	HMDB
Lysophosphatidylcholine(20:4W3/0:0)	HMDB
1-(8Z,11Z,14Z,17Z-Eicosapentaenoyl)-glycero-3-phosphocholine	HMDB
1-Eicsoatetraenoylglycerophosphocholine	HMDB

Chemical Formula

C₂₈H₅₀NO₇P

Average Molecular Weight

543.6729

Monoisotopic Molecular Weight

543.332489471

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-2-hydroxy-3-[(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C28H50NO7P/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/h6-7,9-10,12-13,15-16,27,30H,5,8,11,14,17-26H2,1-4H3/b7-6-,10-9-,13-12-,16-15-/t27-/m1/s1

InChI Key

GOMVPVRDBLLHQC-VEJNOCSESA-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:86259 )
lysophosphatidylcholine 20:4 (CHEBI:86259 )

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	2.41	ALOGPS
logP	1.52	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	24	ChemAxon
Refractivity	165.14 m³·mol⁻¹	ChemAxon
Polarizability	61.24 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	splash10-05a2-4950200000-5f3ea1281b366fbf0bf0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0h2u-9631002000-548020bf93f9ae06ef9b	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("LysoPC(20:4(8Z,11Z,14Z,17Z)/0:0),1TMS,#1" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9153130000-d52f673521111b5098b8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-9383010000-e6c78f8dd918cdfd3908	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052r-9041000000-8835fa70061dabb71b87	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udu-0079170000-3ec998bd7f23091d2628	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0059200000-8a262b7e1a3a9274ec32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0ug0-9288000000-824a302e9a9fcf612010	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000190000-77ea54490e84a8b3b537	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udo-0002990000-bf882252024772103db4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0j4l-0309400000-b3d902f7c0961b2949cb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000090000-3472f30822b8e8601036	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0aor-0000090000-36674ea865affe2dc312	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pcr-1609090000-dfdd3aa00d18d17c8130	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000090000-0fde8b52b527d51cb487	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-0009070000-40ae7eb8536816f65fef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0039030000-a665ab26fc9f4e63275e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0003090000-6ea8042d7f2a61358243	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1029010000-b64d2c578dde5bd000a1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-1009000000-235bb8cd3066c2669bea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0000090000-b4c66c94aa69a4a40271	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001l-0900060000-53fafe765bf1daa88e60	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-0910040000-d12a6e3ffba0751a322d	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected and Quantified	3.8534 +/- 0.9951 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.3257 +/- 1.2805 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5813 +/- 0.8733 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.7131 +/- 1.0789 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.0815 +/- 0.8821 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.639 +/- 1.0678 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	4.0264 +/- 2.6336 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4468 +/- 1.3989 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5689 +/- 1.1102 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.4938 +/- 1.125 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.5246 +/- 0.888 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	3.2693 +/- 0.6831 uM	Normal	Ovine	Goldansaz et al.,...	details