Livestock Metabolome Database: Showing metabocard for PC(16:0/18:2(9Z,12Z)) (LMDB00490)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:51:00 UTC

Update Date

2016-07-20 21:01:35 UTC

Lmdb

LMDB00490

Secondary Accession Numbers

None

Metabolite Identification

Common Name

PC(16:0/18:2(9Z,12Z))

Description

PC(16:0/18:2(9Z,12Z)) 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(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. 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-Palmitoyl-2-linoleoyl-GPC	ChEBI
1-Palmitoyl-2-linoleoyl-GPC (16:0/18:2)	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphocholine	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-phosphatidylcholine	ChEBI
1-Palmitoyl-2-linoleoyl-sn-glycerophosphatidylcholine	ChEBI
1-Palmitoyl-2-linoleoylphosphatidylcholine	ChEBI
GPC(16:0/18:2)	ChEBI
GPCho 16:0/18:2(9Z,12Z)	ChEBI
GPCho(16:0/18:2(9Z,12Z))	ChEBI
GPCho(16:0/18:2)	ChEBI
GPCho(16:0/18:2omega6)	ChEBI
Lecithin	ChEBI
PC 16:0/18:2(9Z,12Z)	ChEBI
PC(16:0/18:2)	ChEBI
PC(16:0/18:2omega6)	ChEBI
PC(34:2)	ChEBI
Phosphatidylcholine 16:0/18:2(9Z,12Z)	ChEBI
Phosphatidylcholine(16:0/18:2(9Z,12Z))	ChEBI
Phosphatidylcholine(16:0/18:2)	ChEBI
Phosphatidylcholine(16:0/18:2omega6)	ChEBI
Gpcho(34:2)	HMDB
Phosphatidylcholine(34:2)	HMDB
2-Linoleoyl-1-palmitoyl-sn-phosphatidylcholine	HMDB
Palmitoyl-linoleoatephosphatidylcholine	HMDB
PLPC	HMDB
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine	HMDB
1-Palmitoyl-2-linoleoyl-3-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-3-sn-glycerophosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-3-sn-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphatidylcholine	HMDB
1-Palmitoyl-2-linoleoyllecithin	HMDB
GPC(16:0/18:2(9Z,12Z))	HMDB
GPC(16:0/18:2n6)	HMDB
GPC(16:0/18:2W6)	HMDB
GPC(34:2)	HMDB
GPCho(16:0/18:2n6)	HMDB
GPCho(16:0/18:2W6)	HMDB
L-alpha-1-Palmitoyl-2-linoleoylphosphatidylcholine	HMDB
L-Α-1-palmitoyl-2-linoleoylphosphatidylcholine	HMDB
PC(16:0/18:2n6)	HMDB
PC(16:0/18:2W6)	HMDB
Phosphatidylcholine(16:0/18:2n6)	HMDB
Phosphatidylcholine(16:0/18:2W6)	HMDB
PC(16:0/18:2(9Z,12Z))	Lipid Annotator, ChEBI

Chemical Formula

C₄₂H₈₀NO₈P

Average Molecular Weight

758.0603

Monoisotopic Molecular Weight

757.562155053

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C42H80NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h14,16,20-21,40H,6-13,15,17-19,22-39H2,1-5H3/b16-14-,21-20-/t40-/m1/s1

InChI Key

JLPULHDHAOZNQI-ZTIMHPMXSA-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

phosphatidylcholine 34:2 (CHEBI:73002 )
Diacylglycerophosphocholines (LMGP01010594 )

Ontology

Status

Detected but not 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	5.48	ALOGPS
logP	8.28	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	40	ChemAxon
Refractivity	227.3 m³·mol⁻¹	ChemAxon
Polarizability	92.66 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
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0udl-0000000490-b7304b809294dbb2ea74	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-0006-0000000940-6acae25b185d1a864052	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0006-0030000910-537e946aca08f069e72b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-002f-0090000700-ecca901df00a9bff124c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-004i-0090000200-fa34aef5028ed4787c4c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-004i-0090000000-d9440bc0e6a9f6cdaf65	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, negative	splash10-004i-0090000000-a5231d807bde53ae849a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 90V, negative	splash10-056r-0090000000-23038428933dc1fcc66d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, negative	splash10-056r-0090000000-ccce70356f7c7b18cbbf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, negative	splash10-056r-1090000000-32df8fc00b6e170aa02a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 157V, negative	splash10-004i-7190000000-811ed3f1fe9d51baf806	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 193V, negative	splash10-004i-9000000000-4bd8d3812cfdbafe42c7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, negative	splash10-0006-0000000900-aed1ee56f1886685cef5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-0006-0000000900-f70fecaaa4c193d6952d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-0006-0000000900-40ddf52a50eed646c5c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-0006-0000000900-79413b6bfab2c2699ebb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 40V, negative	splash10-0006-0020000900-30d6507c6252bceda2ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 46V, negative	splash10-002f-0090000800-e35e5d8e6ef65358f1d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, negative	splash10-004i-0090000200-d82c61ca09093ce2f75a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 59V, negative	splash10-004i-0090000000-a788f61f6153073cc513	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 71V, negative	splash10-056r-0090000000-5242b45696e3aa936e70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 89V, negative	splash10-056r-0090000000-23038428933dc1fcc66d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-73b8731f1bdde398585f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-37c5a628d36a084e1386	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-003r-1900231200-522c9f77a95c208b08bc	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	24451218	details

External Links

DrugBank ID

DB02306

HMDB ID

HMDB0007973

FooDB ID

FDB030253

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

CPL

Wikipedia Link

Not Available

Chemspider ID

Not Available

ChEBI ID

73002

PubChem Compound ID

5287971

Kegg Compound ID

Not Available

YMDB ID

YMDB01845

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for PC(16:0/18:2(9Z,12Z)) (LMDB00490)

Structure for LMDB00490 (PC(16:0/18:2(9Z,12Z)))