PC(18:0/16:1(9Z)) (YMDB01889)

Identification

YMDB ID

YMDB01889

Name

PC(18:0/16:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(18:0/16:1(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(18:0/16:1(9Z)), in particular, consists of one chain of stearic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. The stearic acid moiety is derived from animal fats, coco butter and sesame oil, 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-stearoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
GPCho(18:0/16:1)
GPCho(18:0/16:1n7)
GPCho(18:0/16:1w7)
Lecithin
PC(18:0/16:1)
PC(18:0/16:1n7)
PC(18:0/16:1w7)
PC(34:1)
Phosphatidylcholine(18:0/16:1)
Phosphatidylcholine(18:0/16:1n7)
Phosphatidylcholine(18:0/16:1w7)
Phosphatidylcholine(34:1)
GPCho(34:1)
1-Stearoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
GPCho(18:0/16:1)
GPCho(18:0/16:1n7)
GPCho(18:0/16:1W7)
PC(18:0/16:1)
PC(18:0/16:1n7)
PC(18:0/16:1W7)
Phosphatidylcholine(18:0/16:1)
Phosphatidylcholine(18:0/16:1n7)
Phosphatidylcholine(18:0/16:1W7)
PC(34:1)
Phosphatidylcholine(34:1)
Lecithin
1-Octadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
PC(18:0/16:1(9Z))

CAS number

Not Available

Weight

Average: 760.0761
Monoisotopic: 759.577805117

InChI Key

QRSPNOMDLRZDPG-RRHRGVEJSA-N

InChI

InChI=1S/C42H82NO8P/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/h17,19,40H,6-16,18,20-39H2,1-5H3/t40-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

lecithin

Chemical Formula

C₄₂H₈₂NO₈P

SMILES

CCCCCCCCCCCCCCCCCC(=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

phosphatidylcholine 34:1 (CHEBI:86097 )
Diacylglycerophosphocholines (LMGP01010744 )

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	5.59	ALOGPS
logP	8.64	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	41	ChemAxon
Refractivity	226.18 m³·mol⁻¹	ChemAxon
Polarizability	93.15 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
1 ± 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-7090141300-542ab84f8c3b3e9a5d2e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00n0-3191020000-abf8d2b0306613394d45	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-8193021000-ceb70c94ab612ef42b78	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0kur-0090000200-0669954e10e681e8447b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-0090001000-bb8d5210832bdd5c7795	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kx9-3090000000-5f609a4f6bdd3cbd2e32	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000000900-5c2654109ac5e1768f70	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090032800-de90cd6f95f8e67a6d26	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1090000000-5ede1d32cbb5c488aeed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000900-c437fa62968cd6370d11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014i-0000000900-5d47ab6a1cc6748bc9e4	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0100390200-486972aab32bb882057b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-fc5ea85eb3704fac1e2a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-91dd06610a8a97fa32c6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900230300-85b09124d42ea56a35ca	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0000000900-b3c6e728ecd1d8ae0cd1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0030000900-da2711afa09de91feb17	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uf6-0090000400-15a15f3d3a4ccc0fbf56	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-122890d5f0b74a98dbf8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000900-03d1b99daac1f51a0754	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0500390200-f4006fcdb68b00a06a6a	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	86097
HMDB ID	HMDB08035
Pubchem Compound ID	24778811
Kegg ID	C00157
ChemSpider ID	24766702
FOODB ID	FDB025226
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xadb1670c>