Livestock Metabolome Database: Showing metabocard for PC(22:1(13Z)/16:0) (LMDB00516)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:36 UTC

Update Date

2016-07-20 20:43:55 UTC

Lmdb

LMDB00516

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(22:1(13Z)/16:0)

Description

PC(22:1(13Z)/16:0) 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(22:1(13Z)/16:0), in particular, consists of one chain of erucic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The erucic acid moiety is derived from seed oils and avocados, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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-palmitoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
Phosphatidylcholine(22:1/16:0)	Lipid Annotator, HMDB
PC(22:1/16:0)	Lipid Annotator, HMDB
Lecithin	Lipid Annotator, HMDB
GPCho(22:1/16:0)	Lipid Annotator, HMDB
PC(22:1(13Z)/16:0)	Lipid Annotator
PC(38:1)	Lipid Annotator, HMDB
GPCho(38:1)	Lipid Annotator, HMDB
1-(13Z-docosenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine	Lipid Annotator, HMDB
Phosphatidylcholine(38:1)	Lipid Annotator, HMDB

Chemical Formula

C₄₆H₉₀NO₈P

Average Molecular Weight

816.1825

Monoisotopic Molecular Weight

815.640405373

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C46H90NO8P/c1-6-8-10-12-14-16-18-20-21-22-23-24-25-27-28-30-32-34-36-38-45(48)52-42-44(43-54-56(50,51)53-41-40-47(3,4)5)55-46(49)39-37-35-33-31-29-26-19-17-15-13-11-9-7-2/h20-21,44H,6-19,22-43H2,1-5H3/b21-20-/t44-/m1/s1

InChI Key

QZSYHJOHCCQKPM-UIJSWADASA-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

Not Available

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	6.18	ALOGPS
logP	10.42	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	45	ChemAxon
Refractivity	244.59 m³·mol⁻¹	ChemAxon
Polarizability	102.34 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-0000000090-123a70ac94952e1ecf8c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0600000090-354614840e8050114b6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900221210-4a706d1eb0fd11405832	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000090-d17cc9f2e04c40271d4b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0159-0600000090-4e0af8ace5b38c15a423	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900221210-8f7c09b7b1e1332d6497	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000090-fafea064891dca62fe05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0011000090-be153c32daef08448139	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-14ii-0099000090-ab1e9e10633b6cedb557	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000090-eed84c7b3afaefc0b329	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000000190-56c345257178e7d94fc0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4k-0700159110-c7ee017481abe7f5480a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-af4de0e45bb454a25d41	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08fr-0045004390-eaa3b54c94ca6c8df6d5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052r-6269700000-036de9179acd3f868ae0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-b3f387669b68246e1b40	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000000190-ea998b7ccb9534535add	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-0200498220-2b647c6cb861e89f801b	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 but not Quantified	Not Applicable	Not Available	Bovine	24630653	details
Ruminal Fluid	Detected and Quantified	0.091 +/- 0.003 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	0.34 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.41 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.32 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	0.48 uM	Not Available	Porcine	Barbara U. Metzle...	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0008561

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

Not Available

ChEBI ID

Not Available

PubChem Compound ID

53479171

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)/16:0) (LMDB00516)

Structure for LMDB00516 (PC(22:1(13Z)/16:0))