PC(18:1(11Z)/16:1(9Z)) (YMDB01909)

Identification

YMDB ID

YMDB01909

Name

PC(18:1(11Z)/16:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:1(11Z)/16:1(9Z)) 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)/16:1(9Z)), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the palmitoleic acid moiety is derived from animal fats and vegetable 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

1-vaccenoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
GPCho(18:1/16:1)
GPCho(18:1n7/16:1n7)
GPCho(18:1w7/16:1w7)
GPCho(34:2)
Lecithin
PC(18:1/16:1)
PC(18:1n7/16:1n7)
PC(18:1w7/16:1w7)
Phosphatidylcholine(18:1/16:1)
Phosphatidylcholine(18:1n7/16:1n7)
Phosphatidylcholine(18:1w7/16:1w7)
Phosphatidylcholine(34:2)
PC(34:2)
1-Vaccenoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
Gpcho(18:1/16:1)
Gpcho(18:1n7/16:1n7)
Gpcho(18:1W7/16:1W7)
Gpcho(34:2)
Lecithin
PC Aa C34:2
PC(18:1/16:1)
PC(18:1n7/16:1n7)
PC(18:1W7/16:1W7)
Phosphatidylcholine(18:1/16:1)
Phosphatidylcholine(18:1n7/16:1n7)
Phosphatidylcholine(18:1W7/16:1W7)
Phosphatidylcholine(34:2)
1-(11Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
PC(18:1(11Z)/16:1(9Z))

CAS number

Not Available

Weight

Average: 758.0603
Monoisotopic: 757.562155053

InChI Key

FDBAKEKHEMZAPT-RRHRGVEJSA-N

InChI

InChI=1S/C42H80NO8P/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/h16-19,40H,6-15,20-39H2,1-5H3/t40-/m1/s1

IUPAC Name

(2-{[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(11Z)-octadec-11-enoyloxy]propyl phosphonato]oxy}ethyl)trimethylazanium

Traditional IUPAC Name

lecithin

Chemical Formula

C₄₂H₈₀NO₈P

SMILES

CCCCCCC=CCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCC

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 (LMGP01012147 )

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	2.5e-05 g/L	ALOGPS
logP	5.44	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	91.54 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
3 ± 0 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, Positive	splash10-000i-7090141300-a987835ba159c5539e43	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-3291010000-511abfa268c8523fc750	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-8093032000-fce3622382522495b990	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0lz9-0090000200-e5444ac1f827f91c4bd4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0090001000-c45f4a0a6c392bb005e9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0m1r-3090000000-1aa2f0258b245f5008a3	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-4f45d46462d3badb869e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090032800-13cef569779d0f23eb5f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1090100000-774f20bcf9b43bf30e63	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-02ab676d31620f046e54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000000900-80f99b213a3cb752bf9c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100390200-652b5161d9c2cb1b0984	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-b382b9772ae071121f32	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a59-0600000900-e509931f6dd2f1ba96fd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900231200-c69772b3d60645bd7fa7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-8ecd56b42b9f6b271e5d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-ab98c2d6a7f897263cd4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500390200-462303c5fc844785f467	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-e3f5d1861df776418aef	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-80e8e19a84edd518095b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uf6-0090000400-79f4ee6d8252a51c2b49	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	89678
HMDB ID	HMDB08068
Pubchem Compound ID	53478719
Kegg ID	C00157
ChemSpider ID	24766732
FOODB ID	FDB025259
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xb064d13c>