PC(16:0/18:0) (YMDB01182)

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Identification

YMDB ID

YMDB01182

Name

PC(16:0/18:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(16:0/18:0) 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(16:0/18:0), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one octadecanoyl 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-stearoyl-sn-glycero-3-phosphocholine
1,2-Diacyl-sn-glycero-3-phosphocholine
3-O-sn-Phosphatidyl-L-serine
3-sn-Phosphatidylcholine
Choline phosphatide
GPCho(16:0/18:0)
GPCho(34:0)
Lecithin
Lecithins
O3-Phosphatidyl-L-serine
PC(16:0/18:0)
PC(34:0)
Phosphatidyl-L-serine
phosphatidyl-L-serines
Phosphatidyl-N-trimethylethanolamine
Phosphatidylcholine
Phosphatidylcholine(16:0/18:0)
Phosphatidylcholine(34:0)
(2R)-3-(Palmitoyloxy)-2-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphate
1-Palmitoyl-2-stearoyl-GPC
1-Palmitoyl-2-stearoyl-GPC (16:0/18:0)
1-Palmitoyl-2-stearoyl-sn-glycero-3-phosphorylcholine
1-Palmitoyl-2-stearoylphosphatidylcholine
GPC(16:0/18:0)
(2R)-3-(Palmitoyloxy)-2-(stearoyloxy)propyl 2-(trimethylammonio)ethyl phosphoric acid
1-Hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
1-Palmitoyl-2-stearoyl-sn-glycero-phosphatidylcholine
GPC(34:0)
PSPC

CAS number

8002-43-5

Weight

Average: 762.092
Monoisotopic: 761.593455181

InChI Key

PZNPLUBHRSSFHT-RRHRGVEJSA-N

InChI

InChI=1S/C42H84NO8P/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/h40H,6-39H2,1-5H3/t40-/m1/s1

IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Traditional IUPAC Name

(2-{[(2R)-3-(hexadecanoyloxy)-2-(octadecanoyloxy)propyl phosphono]oxy}ethyl)trimethylazanium

Chemical Formula

C₄₂H₈₄NO₈P

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC

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 34:0 (CHEBI:73000 )
Diacylglycerophosphocholines (LMGP01010573 )

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	2.2e-05 g/L	ALOGPS
logP	5.62	ALOGPS
logP	9	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	42	ChemAxon
Refractivity	225.07 m³·mol⁻¹	ChemAxon
Polarizability	95.56 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(16:0/18:0)	PW002932

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

Not Available

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
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 30V, negative	splash10-0a4i-0000000490-d88f2a12c72c6e16b54c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 36V, negative	splash10-052b-0000000950-8d9dfe7e55c52dab1c77	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 42V, negative	splash10-0002-0020000910-01911c1e0f87c8e49b15	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 48V, negative	splash10-000t-0090000800-80590273ac2914fa2bac	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 54V, negative	splash10-053r-0090000200-9b2292a7f9bcea1dc8c9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 60V, negative	splash10-053r-0090000100-330d9a7ac1ed8c7dddf5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 73V, negative	splash10-053r-0090000000-ee0d4df936e8eb46d224	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 91V, negative	splash10-053r-0090000000-4130545053cd0c87703f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 109V, negative	splash10-053r-0090000000-375f7f0bcf027901b6ab	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 134V, negative	splash10-053r-0090000000-1061c43309feed382466	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 158V, negative	splash10-057i-5090000000-e95f748355aa842e15db	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 196V, negative	splash10-004i-9000000000-1a84ff016029161234df	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, negative	splash10-0002-0000000900-6e195caba9da71e7c374	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-03di-0500000900-95b01663df695379be1f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, positive	splash10-001i-0300000900-62c4e365b0fafe8efec9	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, positive	splash10-03dl-0008900000-be1d0d6b38f1002d172b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, positive	splash10-01ox-0109500000-392db28d858abd8bb315	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 53V, positive	splash10-054k-0000970100-8d9eb2bbec5f813ae4a7	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0kkb-0000690700-eaeb1022d870966c8373	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0bu9-0090000200-7f7015fd1f2dab155708	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0090001000-0fb9ba9bcef10544408b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5i-3090000000-a3206c8150970740995d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000900-9125bd0d43e31222ebc9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0030000900-a6c60e32bbd2feacba2d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a62-0090000400-36b22ac20ecd43e2bd0e	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	HMDB07970
Pubchem Compound ID	6323481
Kegg ID	C00157
ChemSpider ID	24766643
FOODB ID	FDB025161
Wikipedia	Lecithin
BioCyc ID	PHOSPHATIDYLCHOLINE

Structure for #<Compound:0xa525006c>