PC(16:0/18:1(9Z)) (YMDB01183)

Identification

YMDB ID

YMDB01183

Name

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

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(16:0/18:1(9Z)) is a phosphatidylchloline (PC). It is a glycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylcholines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PC(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl to the C-2 atom. In E. coli, PCs can be found in the integral component of the cell outer membrane. They are hydrolyzed by Phospholipases to a 2-acylglycerophosphocholine and a carboxylate.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine
1,2-Diacyl-sn-glycero-3-phosphocholine
3-O-sn-Phosphatidyl-L-serine
3-sn-Phosphatidylcholine
Choline phosphatide
GPCho(16:0/18:1)
GPCho(16:0/18:1n9)
GPCho(16:0/18:1w9)
GPCho(34:1)
Lecithin
Lecithins
O3-Phosphatidyl-L-serine
PC(16:0/18:1)
PC(16:0/18:1n9)
PC(16:0/18:1w9)
PC(34:1)
Phosphatidyl-L-serine
phosphatidyl-L-serines
Phosphatidyl-N-trimethylethanolamine
Phosphatidylcholine
Phosphatidylcholine(16:0/18:1)
Phosphatidylcholine(16:0/18:1n9)
Phosphatidylcholine(16:0/18:1w9)
Phosphatidylcholine(34:1)
1-16:0-2-18:1-Phosphatidylcholine
1-Hexadecanoyl-2-oleoyl-sn-glycero-3-phosphocholine
1-Palmitoyl-2-oleoyl-GPC
1-Palmitoyl-2-oleoyl-GPC (16:0/18:1)
1-Palmitoyl-2-oleoyl-lecithin
1-Palmitoyl-2-oleoylphosphatidylcholine
1-Palmotoyl-2-oleoylglycero-3-phosphocholine
1-POPC
16:0-18:1-PC
GPC(16:0/18:1)
GPCho(16:0/18:1omega9)
Palmitoyloleoylphosphatidylcholine
PC(16:0/18:1omega9)
Phosphatidylcholine(16:0/18:1omega9)
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphatidylcholine
alpha-Phosphatidylcholine-beta-oleoyl-gamma-palmitoyl
1-Palmitoyl-2-oleoyl-phosphatidylcholine
1-Palmitoyl-2-oleoylphosphatidylcholine, (R)-(Z)-isomer
POPC Lipid
beta-Oleoyl-gamma-palmitoyl-L-alpha-phosphatidylcholine
1-hexadecanoyl-2-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
PC(16:0/18:1(9Z))
1-Palmitoyl-2-oleoyl-3-sn-phosphatidylcholine
1-Palmitoyl-2-oleoyl-L-alpha-lecithin
1-Palmitoyl-2-oleoyl-L-alpha-phosphatidylcholine
1-Palmitoyl-2-oleoyl-L-α-lecithin
1-Palmitoyl-2-oleoyl-L-α-phosphatidylcholine
1-Palmitoyl-2-oleoyl-sn-3-phosphocholine
1-Palmitoyl-2-oleoyl-sn-glycero-3-phosphorylcholine
1-Palmitoyl-2-oleoyl-sn-glycero-phosphatidylcholine
1-Palmitoyl-2-oleoyl-sn-glycero-phosphocholine
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphatidylcholine
1-Palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine
1-Palmitoyl-2-oleoyl-sn-glyceryl-3-phosphorylcholine
1-Palmitoyl-2-oleoyllecithin
1-Palmitoyl-2-oleyl-3-sn-phosphatidylcholine
2-Oleo-1-palmitin phosphate choline ester
2-Oleoyl-1-palmitoyl-sn-glycero-3-phosphocholine
2-Oleoyl-1-palmitoyllecithin
GPC(16:0/18:1(9Z))
GPC(16:0/18:1n9)
GPC(16:0/18:1w9)
GPC(34:1)
GPCho(16:0/18:1(9Z))
L-1-Palmitoyl-2-oleoylphosphatidylcholine
L-Palmitoyloleoylphosphatidylcholine
L-alpha-1-Palmitoyl-2-oleoylphosphatidylcholine
L-α-1-Palmitoyl-2-oleoylphosphatidylcholine
POPC
Phosphatidylcholine(16:0/18:1(9Z))
β-Oleoyl-γ-palmitoyl-L-α-phosphatidylcholine

CAS number

8002-43-5

Weight

Average: 760.0761
Monoisotopic: 759.577805117

InChI Key

WTJKGGKOPKCXLL-VYOBOKEXSA-N

InChI

InChI=1S/C42H82NO8P/c1-6-8-10-12-14-16-18-20-21-23-25-27-29-31-33-35-42(45)51-40(39-50-52(46,47)49-37-36-43(3,4)5)38-48-41(44)34-32-30-28-26-24-22-19-17-15-13-11-9-7-2/h20-21,40H,6-19,22-39H2,1-5H3/b21-20-/t40-/m1/s1

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-[(9Z)-octadec-9-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Chemical Formula

C₄₂H₈₂NO₈P

SMILES

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

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:73001 )
Diacylglycerophosphocholines (LMGP01010005 )

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	94 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

Glycerophospholipid metabolism	PW002493
Phosphatidylcholine biosynthesis PC(16:0/18:1(9Z))	PW002914

KEGG Pathways

Arachidonic acid metabolism	ec00590
Glycerophospholipid metabolism	ec00564
Linoleic acid metabolism	ec00591
alpha-Linolenic acid metabolism	ec00592

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
346750 ± 32150 umol/L	SD media with 2% raffinose	24 oC	BY4741	PMID: 19174513
1557500 ± 4475 umol/L	SD media with 2% raffinose	37 oC	BY4741	PMID: 19174513
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
LC-MS/MS	LC-MS/MS Spectrum - QqQ 1V, negative	splash10-000t-0090200800-c8db3c4042d858672ebd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - IT 40V, negative	splash10-0006-0020000900-603012fb0ce5ff46f1ea	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, negative	splash10-0udi-0000000190-afc4cd2ac0e64fa39623	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0udl-0000000490-09171592a6955e57e163	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-0f6x-0000000940-3b9edba3cc0cdfff4945	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0006-0030000910-e80b4b8f6690eea16c9d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-000x-0090000700-527aadfe756a5f2ad9a5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-053r-0090000200-e27632edecd3a83538a4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-053r-0090000000-875a5d38cc2b636df4a1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 72V, negative	splash10-053r-0090000000-6bdad7ea857755dad8df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, negative	splash10-053r-0090000000-a0160ca0a20b8ca408de	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, negative	splash10-053r-0090000000-d2bc446076d9d86bbadf	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 133V, negative	splash10-053r-1090000000-a94d8052959d35d3d25e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 157V, negative	splash10-057i-5190000000-12de950663c450d5ad7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 194V, negative	splash10-004i-9000000000-906a0ebc0dd0220ac288	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, negative	splash10-0006-0000000900-0bfd0ce87b7b119d82fb	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 22V, negative	splash10-0006-0000000900-88f30608c9fd0df934c2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-0006-0000000900-fb159b53855796db7d35	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 34V, negative	splash10-0006-0000000900-084480cec1d6930fa834	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 41V, negative	splash10-0006-0020000900-103adeac53f876868122	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 47V, negative	splash10-000x-0090000800-a9198efdf2f4fe5ec5da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 53V, negative	splash10-053r-0090000200-9df170809bae304c6bc1	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000000900-64875131a83d4fda43e6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03e9-0600000900-dfb450caf9537c97446e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fai-1900230300-31ec54e207b217422a2e	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	18303
HMDB ID	HMDB07972
Pubchem Compound ID	6323481
Kegg ID	C00157
ChemSpider ID	4593686
FOODB ID	FDB030200
Wikipedia	Lecithin
BioCyc ID	PHOSPHATIDYLCHOLINE

Structure for #<Compound:0xaef08288>