Livestock Metabolome Database: Showing metabocard for PC(22:1(13Z)/18:1(11Z)) (LMDB00543)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:52:11 UTC

Update Date

2021-04-30 20:57:48 UTC

Lmdb

LMDB00543

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(22:1(13Z)/18:1(11Z))

Description

PC(22:1(13Z)/18:1(11Z)) 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(22:1(13Z)/18:1(11Z)), in particular, consists of one chain of erucic acid at the C-1 position and one chain of vaccenic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the vaccenic acid moiety is derived from butter fat and animal fat. 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
1-Erucoyl-2-vaccenoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(22:1/18:1)	HMDB
Gpcho(22:1n9/18:1n7)	HMDB
Gpcho(22:1W9/18:1W7)	HMDB
Gpcho(40:2)	HMDB
Lecithin	HMDB
PC Aa C40:2	HMDB
PC(22:1/18:1)	HMDB
PC(22:1n9/18:1n7)	HMDB
PC(22:1W9/18:1W7)	HMDB
PC(40:2)	HMDB
Phosphatidylcholine(22:1/18:1)	HMDB
Phosphatidylcholine(22:1n9/18:1n7)	HMDB
Phosphatidylcholine(22:1W9/18:1W7)	HMDB
Phosphatidylcholine(40:2)	HMDB
1-(13Z-Docosenoyl)-2-(11Z-octadecenoyl)-sn-glycero-3-phosphocholine	HMDB
PC(22:1(13Z)/18:1(11Z))	Lipid Annotator

Chemical Formula

C₄₈H₉₂NO₈P

Average Molecular Weight

842.2197

Monoisotopic Molecular Weight

841.656055437

IUPAC Name

(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-[(13Z)-docos-13-enoyloxy]-2-[(11Z)-octadec-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C48H92NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-27-28-30-32-34-36-38-40-47(50)54-44-46(45-56-58(52,53)55-43-42-49(3,4)5)57-48(51)41-39-37-35-33-31-29-26-21-19-17-15-13-11-9-7-2/h17,19-20,22,46H,6-16,18,21,23-45H2,1-5H3/b19-17-,22-20-/t46-/m1/s1

InChI Key

VMYYPARBVHMEFG-WQZYGQBESA-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 (LMGP01012220 )

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	6.36	ALOGPS
logP	10.95	ChemAxon
logS	-7.6	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	254.91 m³·mol⁻¹	ChemAxon
Polarizability	104.88 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000090-d5d4a7344dd9b429532c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-0600000090-12f1e6ed1f67b0bf6f7a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041120-164ee5a9f5e28fa42d82	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000090-334ce021df69056ff46b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000090-b86490a18567af168853	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001j-0700159020-f0a7d7d0e10531ded0b4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0000000090-7798f4de22a79938254a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0011000090-69d774e968327e33ee65	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006i-0099000090-560a493d4d309bd5114e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000090-4b489c53edd2019c68bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-0063004390-9a4f7ad60905bd08207b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-2049200000-b4d528205a4356ef6558	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000090-22c680cb0cae12530752	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-0600000090-2ed5ce7d2651aa92b053	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900041120-a77806ba9056772b030c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000090-22004a077e65cf532e85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000190-063b8600b5379c7321f0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-014i-0100197110-e110a7ee942e5c37c5a2	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
Serum	Detected and Quantified	0.2428 +/- 0.0806 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2236 +/- 0.0684 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.33 +/- 0.15 uM	Not Available	Ovine	Candidate serum m...	details
Serum	Detected and Quantified	0.2369 +/- 0.0614 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2118 +/- 0.0344 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	24888604	details
Serum	Detected and Quantified	0.21 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.23 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.13 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.22 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.2337 +/- 0.0513 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.221 +/- 0.0875 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.225 +/- 0.0517 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2321 +/- 0.0523 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2249 +/- 0.0549 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2303 +/- 0.052 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2962 +/- 0.1772 uM	Normal	Ovine	Goldansaz et al.,...	details
Serum	Detected and Quantified	0.2534 +/- 0.0984 uM	Normal	Ovine	Goldansaz et al.,...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0011202

FooDB ID

FDB027957

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

24767224

ChEBI ID

Not Available

PubChem Compound ID

53480677

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 PC(22:1(13Z)/18:1(11Z)) (LMDB00543)

Structure for LMDB00543 (PC(22:1(13Z)/18:1(11Z)))