PC(18:2(9Z,12Z)/18:0) (YMDB01958)

Identification

YMDB ID

YMDB01958

Name

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

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:2(9Z,12Z)/18:0) 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)/18:0), in particular, consists of one chain of linoleic acid at the C-1 position and one chain of stearic acid at the C-2 position. The linoleic acid moiety is derived from seed oils, while the stearic acid moiety is derived from animal fats, coco butter and sesame 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-stearoyl-sn-glycero-3-phosphocholine
GPCho(18:2/18:0)
GPCho(18:2n6/18:0)
GPCho(36:2)
Lecithin
PC(18:2/18:0)
PC(18:2n6/18:0)
PC(18:2w6/18:0)
PC(36:2)
Phosphatidylcholine(18:2/18:0)
Phosphatidylcholine(18:2n6/18:0)
Phosphatidylcholine(18:2w6/18:0)
Phosphatidylcholine(36:2)
GPCho(18:2w6/18:0)
1-Linoleoyl-2-stearoyl-sn-glycero-3-phosphocholine
GPCho(18:2/18:0)
GPCho(18:2n6/18:0)
PC(18:2/18:0)
PC(18:2n6/18:0)
PC(18:2W6/18:0)
Phosphatidylcholine(18:2/18:0)
Phosphatidylcholine(18:2n6/18:0)
Phosphatidylcholine(18:2W6/18:0)
PC(36:2)
Lecithin
Phosphatidylcholine(36:2)
PC(18:2(9Z,12Z)/18:0)
1-(9Z,12Z-octadecadienoyl)-2-octadecanoyl-sn-glycero-3-phosphocholine
GPCho(36:2)

CAS number

Not Available

Weight

Average: 786.1134
Monoisotopic: 785.593455181

InChI Key

DZPKSVTWWIZUMS-HUESYALOSA-N

InChI

InChI=1S/C44H84NO8P/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-43(46)50-40-42(41-52-54(48,49)51-39-38-45(3,4)5)53-44(47)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2/h14,16,20,22,42H,6-13,15,17-19,21,23-41H2,1-5H3/t42-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

lecithin

Chemical Formula

C₄₄H₈₄NO₈P

SMILES

CCCCCCCCCCCCCCCCCC(=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

phosphatidylcholine 36:2 (CHEBI:86112 )
Diacylglycerophosphocholines (LMGP01010935 )

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	2.2e-05 g/L	ALOGPS
logP	5.8	ALOGPS
logP	9.17	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	42	ChemAxon
Refractivity	236.5 m³·mol⁻¹	ChemAxon
Polarizability	95.83 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
0.755 ± 0.03775 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 LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090001800-b3a1972611ea3769fa43	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-1090103300-a72fcd04de0cb44cf0a2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00pi-3090100000-b54c6a4dd6b6fcfff840	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-23df8d3c4971511f3b91	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0081030900-336842a235f9ccd697d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-4090300000-0657ea1e487e8af6e0c7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-683d2aaf9f12a9d08614	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0030000090-ceb91fadb205f9c1b737	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ji-0090000040-f6fcdf71c4ae55cc490b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9061052400-679dfe0e14e38cdf9f16	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015i-5293022100-3c936433f50aedc64014	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9075021100-adfb6088014ebf04dee3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000090-53a8e01f33b2af13f226	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000000190-64f46bdfe255d6a5b5e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002b-0900369110-8282d7071a7afc84c25d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-64c382f846ba04194d31	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000900-6c06686879d9f7790e62	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0200498400-bfcef54bcce75991df2a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-e54f4b7d729e27672b37	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0019-0600000900-3a2440aaca7e87ec13a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900041300-d3ccf7461dac2d683004	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	86112
HMDB ID	HMDB08135
Pubchem Compound ID	Not Available
Kegg ID	C00157
ChemSpider ID	24766798
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xac306504>