PC(18:2(9Z,12Z)/24:0) (YMDB01974)

Identification

YMDB ID

YMDB01974

Name

PC(18:2(9Z,12Z)/24:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:2(9Z,12Z)/24:0) 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(18:2(9Z,12Z)/24:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the lignoceric 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

1-linoleoyl-2-lignoceroyl-sn-glycero-3-phosphocholine
GPCho(18:2/24:0)
GPCho(18:2n6/24:0)
GPCho(18:2w6/24:0)
GPCho(42:2)
Lecithin
PC(18:2/24:0)
PC(18:2n6/24:0)
PC(18:2w6/24:0)
PC(42:2)
Phosphatidylcholine(18:2/24:0)
Phosphatidylcholine(18:2w6/24:0)
Phosphatidylcholine(42:2)
Phosphatidylcholine(18:2n6/24:0)
Phosphatidylcholine(42:2)
1-Linoleoyl-2-lignoceroyl-sn-glycero-3-phosphocholine
Lecithin
GPCho(42:2)
Phosphatidylcholine(18:2/24:0)
PC(42:2)
GPCho(18:2/24:0)
1-(9Z,12Z-Octadecadienoyl)-2-tetracosanoyl-sn-glycero-3-phosphocholine
PC(18:2/24:0)
PC(18:2(9Z,12Z)/24:0)

CAS number

Not Available

Weight

Average: 870.2729
Monoisotopic: 869.687355565

InChI Key

INOAKRDQRDGXPN-QSCHNALKSA-N

InChI

InChI=1S/C50H96NO8P/c1-6-8-10-12-14-16-18-20-22-23-24-25-26-27-29-31-33-35-37-39-41-43-50(53)59-48(47-58-60(54,55)57-45-44-51(3,4)5)46-56-49(52)42-40-38-36-34-32-30-28-21-19-17-15-13-11-9-7-2/h15,17,21,28,48H,6-14,16,18-20,22-27,29-47H2,1-5H3/t48-/m1/s1

IUPAC Name

trimethyl(2-{[(2R)-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]-2-(tetracosanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional IUPAC Name

lecithin

Chemical Formula

C₅₀H₉₆NO₈P

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCC=CCC=CCCCCC)COP([O-])(=O)OCC[N+](C)(C)C

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 (LMGP01012173 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	2.1e-05 g/L	ALOGPS
logP	6.65	ALOGPS
logP	11.84	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	48	ChemAxon
Refractivity	264.11 m³·mol⁻¹	ChemAxon
Polarizability	108.7 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
0.01 ± 0.0005 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f79-9045041140-1a568ff1c845c0d9c5f0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w39-5259021110-d55078f76b1fff279476	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-8039001100-d3eb84c665b31feda7fb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02vi-0093000030-dc8c57290f0e77399103	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-0091000100-dcc3e17aa1831859dc38	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00or-6097100000-521ecd5c770a93a94f57	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000090-c336174e69b9e1796bba	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0034003090-6f8e4caac07ee264b3ed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00pi-8197700000-a3a078c65d77479ebd02	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000090-1a99a84a66e8fb9335dd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000090-3c6b6ad511895debb4a6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002g-0100179030-68695d9af8fc87ec3ee1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000009-7cbfab51475788a607c8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0011000009-0497d04d07d490e5d2cf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0vmi-0099000009-ff8b419ff6745334e95a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000090-e605ed621546773b38cf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000090-1f36656371040c902947	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4k-0900143930-4da2d5e495c1bacff5d6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-68ac673f23e394c3c146	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000090-d18782d551cf189f549c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900032030-0898d1aab73d432c75f8	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	89589
HMDB ID	HMDB08157
Pubchem Compound ID	53478795
Kegg ID	C00157
ChemSpider ID	24766819
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0x051ea3fc>