Livestock Metabolome Database: Showing metabocard for PC(20:4(5Z,8Z,11Z,14Z)/22:0) (LMDB00512)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:30 UTC

Update Date

2016-07-19 23:32:06 UTC

Lmdb

LMDB00512

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(20:4(5Z,8Z,11Z,14Z)/22:0)

Description

PC(20:4(5Z,8Z,11Z,14Z)/22:0) is a phosphatidylcholine (PC or GPCho). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, glycerophosphocholines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PC(20:4(5Z,8Z,11Z,14Z)/22:0), in particular, consists of one chain of arachidonic acid at the C-1 position and one chain of behenic acid at the C-2 position. The arachidonic acid moiety is derived from animal fats and eggs, while the behenic acid moiety is derived from groundnut oil. Phospholipids, are ubiquitous in nature and are key components of the lipid bilayer of cells, as well as being involved in metabolism and signaling.While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. PCs can be synthesized via three different routes. In one route, choline is activated first by phosphorylation and then by coupling to CDP prior to attachment to phosphatidic acid. PCs can also synthesized by the addition of choline to CDP-activated 1,2-diacylglycerol. A third route to PC synthesis involves the conversion of either PS or PE to PC.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Phosphatidylcholine(42:4)	HMDB
PC(20:4/22:0)	HMDB
Phosphatidylcholine(20:4/22:0)	HMDB
1-Arachidonoyl-2-behenoyl-sn-glycero-3-phosphocholine	HMDB
Lecithin	HMDB
GPCho(20:4/22:0)	HMDB
PC(42:4)	HMDB
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-2-docosanoyl-sn-glycero-3-phosphocholine	HMDB
GPCho(42:4)	HMDB
PC(20:4(5Z,8Z,11Z,14Z)/22:0)	Lipid Annotator

Chemical Formula

C₅₀H₉₂NO₈P

Average Molecular Weight

866.2411

Monoisotopic Molecular Weight

865.656055437

IUPAC Name

(2-{[(2R)-2-(docosanoyloxy)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@]([H])(COC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC)COP([O-])(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C50H92NO8P/c1-6-8-10-12-14-16-18-20-22-24-25-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-26-23-21-19-17-15-13-11-9-7-2/h15,17,21,23,28,30,34,36,48H,6-14,16,18-20,22,24-27,29,31-33,35,37-47H2,1-5H3/b17-15-,23-21-,30-28-,36-34-/t48-/m1/s1

InChI Key

CVECNRQDBOYLEX-YUDFJFIPSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

Phosphatidylcholines

Alternative Parents

Substituents

Diacylglycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Dicarboxylic acid or derivatives
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Quaternary ammonium salt
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Amine
Organic salt
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphocholines (LMGP01011921 )

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	6.63	ALOGPS
logP	11.11	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	111.19 Å²	ChemAxon
Rotatable Bond Count	46	ChemAxon
Refractivity	266.34 m³·mol⁻¹	ChemAxon
Polarizability	106.74 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 (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000090-12c0468d22641f22e505	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0600000090-74413cab6d11bb33047b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041030-e29541dd44a6662e80e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0gw0-0049000040-19e3aaac370fd7b0a6b7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udr-0059000100-f9594bb27d6cbe4eeb7f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0f79-5059100000-4c808c3663364b0e6fc3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-c23bf4396560995f2075	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000090-7ff854621a9c368ce93b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-0100197030-d3a98160891623fbafa1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-885c0d2b6e3e4f892e2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000090-9125665aeeab92b4ca2b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052b-0900161930-b1ec07edb27e71323b93	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000009-1791f8bf865a0857471f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0003000009-1106ee3d4ff4b91b67d1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udr-0009000004-08262e03cf5ef2485552	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-8e865372fc15a66c7bf1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dr-0027003090-a7506553194d0ea7950b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pbi-5129300000-393487632e3c596f444f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000090-3aaaad39472490bbd6f5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0600000090-d0d848a19ec2a7607a12	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041030-5a238d4b4acc48a93de1	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Plasma
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Plasma	Detected and Quantified	0.1475 +/- 0.0166-0.0920+/-0.0166 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	0.1581 +/- 0.0145-0.0792+/-0.0145 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	0.1587 +/- 0.0153-0.1419+/-0.0153 uM	Not Available	Porcine	22492530	details
Plasma	Detected and Quantified	0.1669 +/- 0.0139-0.1451+/-0.0139 uM	Not Available	Porcine	22492530	details
Ruminal Fluid	Detected and Quantified	0.008 +/- 0.004 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	0.11 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.11 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.08 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.11 uM	Not Available	Porcine	Barbara U. Metzle...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0008446

FooDB ID

FDB025636

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

Not Available

ChEBI ID

88904

PubChem Compound ID

52923319

Kegg Compound ID

Not Available

YMDB ID

YMDB02129

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(20:4(5Z,8Z,11Z,14Z)/22:0) (LMDB00512)

Structure for LMDB00512 (PC(20:4(5Z,8Z,11Z,14Z)/22:0))