PC(18:1(11Z)/24:0) (YMDB01926)

Identification

YMDB ID

YMDB01926

Name

PC(18:1(11Z)/24:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:1(11Z)/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(18:1(11Z)/24:0), in particular, consists of one chain of vaccenic acid at the C-1 position and one chain of lignoceric acid at the C-2 position. The vaccenic acid moiety is derived from butter fat and animal fat, 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-vaccenoyl-2-lignoceroyl-sn-glycero-3-phosphocholine
GPCho(18:1n7/24:0)
GPCho(18:1w7/24:0)
GPCho(42:1)
Lecithin
PC(18:1/24:0)
PC(18:1n7/24:0)
PC(18:1w7/24:0)
PC(42:1)
Phosphatidylcholine(18:1/24:0)
Phosphatidylcholine(18:1n7/24:0)
Phosphatidylcholine(18:1w7/24:0)
Phosphatidylcholine(42:1)
GPCho(18:1/24:0)
1-Vaccenoyl-2-lignoceroyl-sn-glycero-3-phosphocholine
Gpcho(18:1n7/24:0)
Gpcho(18:1W7/24:0)
Gpcho(42:1)
Lecithin
PC Aa C42:1
PC(18:1/24:0)
PC(18:1n7/24:0)
PC(18:1W7/24:0)
PC(42:1)
Phosphatidylcholine(18:1/24:0)
Phosphatidylcholine(18:1n7/24:0)
Phosphatidylcholine(18:1W7/24:0)
Phosphatidylcholine(42:1)
1-(11Z-Octadecenoyl)-2-tetracosanoyl-sn-glycero-3-phosphocholine
PC(18:1(11Z)/24:0)

CAS number

Not Available

Weight

Average: 872.2888
Monoisotopic: 871.703005629

InChI Key

FPXADVQYVJYLOJ-QSCHNALKSA-N

InChI

InChI=1S/C50H98NO8P/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/h17,19,48H,6-16,18,20-47H2,1-5H3/t48-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

lecithin

Chemical Formula

C₅₀H₉₈NO₈P

SMILES

CCCCCCCCCCCCCCCCCCCCCCCC(=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 (LMGP01012161 )

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	1.9e-05 g/L	ALOGPS
logP	6.61	ALOGPS
logP	12.2	ChemAxon
logS	-7.7	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	49	ChemAxon
Refractivity	262.99 m³·mol⁻¹	ChemAxon
Polarizability	111.14 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
0.032 ± 0.0016 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	splash10-0f79-9045041140-6a0dc938004815835c01	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0uyr-5259021110-130c5f0c9405a2edfd83	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-8029002110-ccc74c93feabde46b6ff	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-02h9-0093000030-08e712b8320c5c4c76cc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0091000100-6f763e63b8910e4a5919	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02cs-6097100000-90a56376848f9516b7ad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000090-fedb0c557e96d742004f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000090-f2c7c389d57105341225	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dj-0900143930-b254275417314e8751fa	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000009-aa7976ed120b850370e0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0011000009-40d0b001cfd7e276ca87	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0bai-0099000009-8e3290c0048925031a9f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000090-342307a5f81e24ba838b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00e9-0600000090-edd5a97757345b36a380	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900032030-856fb226bf6bd8f3823a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000000090-006e98cedb5140920851	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0000000090-35af76fdb6837b18196a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0100179030-0c92a51662d85275c0fe	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0000000090-f5a92f86761149fa229d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0034003090-2b3605de85a460923fac	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00lr-7197700000-0e780ff634df1d2fd402	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	89704
HMDB ID	HMDB08091
Pubchem Compound ID	53478753
Kegg ID	C00157
ChemSpider ID	24766755
FOODB ID	FDB025282
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xaee8a310>