PC(18:1(11Z)/14:0) (YMDB01907)

Identification

YMDB ID

YMDB01907

Name

PC(18:1(11Z)/14:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:1(11Z)/14:0) 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)/14:0), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of myristic acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, while the myristic acid moiety is derived from nutmeg and butter. 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-myristoyl-sn-glycero-3-phosphocholine
GPCho(18:1/14:0)
GPCho(18:1n7/14:0)
GPCho(32:1)
Lecithin
PC(18:1/14:0)
PC(18:1n7/14:0)
PC(18:1w7/14:0)
PC(32:1)
Phosphatidylcholine(18:1/14:0)
Phosphatidylcholine(18:1n7/14:0)
Phosphatidylcholine(18:1w7/14:0)
Phosphatidylcholine(32:1)
GPCho(18:1w7/14:0)
Phosphatidylcholine(18:1/14:0)
GPCho(18:1/14:0)
Lecithin
GPCho(32:1)
PC(18:1/14:0)
Phosphatidylcholine(32:1)
PC(32:1)
PC(18:1(11Z)/14:0)
1-(11Z-octadecenoyl)-2-tetradecanoyl-sn-glycero-3-phosphocholine
1-vaccenoyl-2-myristoyl-sn-glycero-3-phosphocholine

CAS number

Not Available

Weight

Average: 732.023
Monoisotopic: 731.546504989

InChI Key

ZBQGASWGCNJQQT-KXQOOQHDSA-N

InChI

InChI=1S/C40H78NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-24-26-28-30-32-39(42)46-36-38(37-48-50(44,45)47-35-34-41(3,4)5)49-40(43)33-31-29-27-25-22-17-15-13-11-9-7-2/h16,18,38H,6-15,17,19-37H2,1-5H3/t38-/m1/s1

IUPAC Name

trimethyl(2-{[(2R)-3-[(11Z)-octadec-11-enoyloxy]-2-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional IUPAC Name

lecithin

Chemical Formula

C₄₀H₇₈NO₈P

SMILES

CCCCCCCCCCCCCC(=O)O[C@H](COC(=O)CCCCCCCCCC=CCCCCCC)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 (LMGP01012145 )

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	2.6e-05 g/L	ALOGPS
logP	5.25	ALOGPS
logP	7.75	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	39	ChemAxon
Refractivity	216.98 m³·mol⁻¹	ChemAxon
Polarizability	89.59 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
0.098 ± 0.0049 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	splash10-01q0-8190141300-62f25feb96b984e5003b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-02u9-4491020100-e82ef04c569ba8a1ec85	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0019-9363022000-969051b183068c5f4146	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000200-a9ddf5ccdf06e5201ff9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0090001000-1386a80f6c12c4b14b4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-3190000000-b48f67df0030613cfe45	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0000000900-692892d313dcd3995c61	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0000001900-d2164a22b9f090f20896	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0101491100-b42d46f73ce97f6a5ae8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-8dbe5f937df1e45f5cec	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0081043900-11a124169cbf03f23110	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-003r-3290400000-1b89f4affacbcbfb7122	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-6ea32ad4dc08edccb04b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-909418a92ec1ce82912b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ff0-1900231200-027f616f3f576c3277a6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-72e4b10a8d04de492e21	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0000001900-6d29a9c4f6d92278bb69	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00dk-0600491100-1cf4d4ff35ffc6a2d9ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-27ef027a037d0c8fadfd	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0030000900-62ce39d263a778534931	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ai-0090000400-bc1655a81dd28d38491f	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	HMDB08064
Pubchem Compound ID	53478711
Kegg ID	C00157
ChemSpider ID	24766728
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xad43bedc>