Livestock Metabolome Database: Showing metabocard for PC(18:1(11Z)/16:0) (LMDB00501)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:16 UTC

Update Date

2016-07-20 20:43:39 UTC

Lmdb

LMDB00501

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(18:1(11Z)/16:0)

Description

PC(18:1(11Z)/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(18:1(11Z)/16:0), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, 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-Vaccenoyl-2-palmitoyl-sn-glycero-3-phosphocholine	HMDB
Gpcho(18:1/16:0)	HMDB
Gpcho(18:1n7/16:0)	HMDB
Gpcho(18:1W7/16:0)	HMDB
Gpcho(34:1)	HMDB
Lecithin	HMDB
PC Aa C34:1	HMDB
PC(18:1/16:0)	HMDB
PC(18:1n7/16:0)	HMDB
PC(18:1W7/16:0)	HMDB
PC(34:1)	HMDB
Phosphatidylcholine(18:1/16:0)	HMDB
Phosphatidylcholine(18:1n7/16:0)	HMDB
Phosphatidylcholine(18:1W7/16:0)	HMDB
Phosphatidylcholine(34:1)	HMDB
1-(11Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphocholine	HMDB
PC(18:1(11Z)/16:0)	Lipid Annotator

Chemical Formula

C₄₂H₈₂NO₈P

Average Molecular Weight

760.0761

Monoisotopic Molecular Weight

759.577805117

IUPAC Name

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

Traditional Name

lecithin

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-24-26-28-30-32-34-41(44)48-38-40(39-50-52(46,47)49-37-36-43(3,4)5)51-42(45)35-33-31-29-27-25-22-19-17-15-13-11-9-7-2/h16,18,40H,6-15,17,19-39H2,1-5H3/b18-16-/t40-/m1/s1

InChI Key

WPAONTMCEBPEAF-KWNHIAGJSA-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 (LMGP01012146 )

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	5.58	ALOGPS
logP	8.64	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	41	ChemAxon
Refractivity	226.18 m³·mol⁻¹	ChemAxon
Polarizability	93.84 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	splash10-03di-0000000900-64875131a83d4fda43e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-dfb450caf9537c97446e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-1900230300-31ec54e207b217422a2e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-fc5ea85eb3704fac1e2a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-91dd06610a8a97fa32c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900230300-10b8449ffe5fd02447c1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-5c2654109ac5e1768f70	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0081043900-aa90ffc4fd4732d8a5d8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053r-3190400000-011d7b4fad74221ea484	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-c437fa62968cd6370d11	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000000900-5d47ab6a1cc6748bc9e4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100390200-23190823d11b53855b76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-122890d5f0b74a98dbf8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-03d1b99daac1f51a0754	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500190100-8208b795ba85536babf4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-b3c6e728ecd1d8ae0cd1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-bf81a9b0f9d9baf1ad05	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a66-0090000400-374088f1c13fb1e9653d	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	0.027 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.03 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.034 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.3 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	0.14 +/- 0.145 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.227 +/- 0.120 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.231 +/- 0.165 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.312 +/- 0.284 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	0.312 +/- 0.284 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Serum	Detected and Quantified	76.9 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	83 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	53.7 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected and Quantified	75.6 uM	Not Available	Porcine	Barbara U. Metzle...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Caprine	24214495	details