PC(14:1(9Z)/16:1(9Z)) (YMDB01178)

Identification

YMDB ID

YMDB01178

Name

PC(14:1(9Z)/16:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(14:1(9Z)/16:1(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(14:1(9Z)/16:1(9Z)), in particular, consists of one 9Z-tetradecenoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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-myristoleoyl-2-palmitoleoyl-sn-glycero-3-phosphocholine
1,2-Diacyl-sn-glycero-3-phosphocholine
3-O-sn-Phosphatidyl-L-serine
3-sn-Phosphatidylcholine
Choline phosphatide
GPCho(14:1/16:1)
GPCho(14:1n5/16:1n7)
GPCho(14:1w5/16:1w7)
GPCho(30:2)
Lecithin
Lecithins
O3-Phosphatidyl-L-serine
PC(14:1/16:1)
PC(14:1n5/16:1n7)
PC(14:1w5/16:1w7)
PC(30:2)
Phosphatidyl-L-serine
phosphatidyl-L-serines
Phosphatidyl-N-trimethylethanolamine
Phosphatidylcholine
Phosphatidylcholine(14:1/16:1)
Phosphatidylcholine(14:1n5/16:1n7)
Phosphatidylcholine(14:1w5/16:1w7)
Phosphatidylcholine(30:2)
1-(9Z-Tetradecenoyl)-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphocholine
PC(14:1(9Z)/16:1(9Z))

CAS number

8002-43-5

Weight

Average: 701.9539
Monoisotopic: 701.499554797

InChI Key

RUTXZOOOUKHIRR-KQGJYXFZSA-N

InChI

InChI=1S/C38H72NO8P/c1-6-8-10-12-14-16-18-19-21-23-25-27-29-31-38(41)47-36(35-46-48(42,43)45-33-32-39(3,4)5)34-44-37(40)30-28-26-24-22-20-17-15-13-11-9-7-2/h13,15-16,18,36H,6-12,14,17,19-35H2,1-5H3/b15-13-,18-16-/t36-/m1/s1

IUPAC Name

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

Traditional IUPAC Name

lecithin

Chemical Formula

C₃₈H₇₂NO₈P

SMILES

CCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(COC(=O)CCCCCCC\C=C/CCCC)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 (LMGP01011385 )

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	3.4e-05 g/L	ALOGPS
logP	4.76	ALOGPS
logP	6.5	ChemAxon
logS	-7.4	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	36	ChemAxon
Refractivity	208.9 m³·mol⁻¹	ChemAxon
Polarizability	83.63 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(14:1(9Z)/16:1(9Z))	PW002847

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
0.018 ± 0.0009 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
175250 ± 1475 umol/L	SD media with 2% raffinose	24 oC	BY4741	PMID: 19174513
22500 ± 425 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00kf-0000915000-70cc220ef0e06e106fa6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zi0-0090000200-a647583b7468aca22802	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-0190000000-4a412e5f8d73402c5ed6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-4290000000-03989d55493c73536a31	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0000000900-5e86fac3277edd257bad	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-0000001900-d689ed047e4811394499	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-0700691100-b1b962c108a0c0b79340	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0000000900-015b7563f35058194e4b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0030000900-fd2ae918b9bd28bf4ae8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uii-0090000400-cd9d490ca073d32c9e59	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-c0264bc5a3658a84089e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000001900-f99701a4c0dc029e939b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fis-0101791100-07091dabbadf7fa8ebb0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000000900-c0783fc627a546653f44	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090042700-0c9a81041296cc2790ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fb9-3394000000-397dae97836f53018b88	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000000900-1fd7bbea2430b811e0ce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-0600000900-4b1c66063a5797985307	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-1900412100-d5b06fcc3b23dd902711	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	HMDB07903
Pubchem Compound ID	6323481
Kegg ID	C00157
ChemSpider ID	24766579
FOODB ID	Not Available
Wikipedia	Lecithin
BioCyc ID	PHOSPHATIDYLCHOLINE

Structure for #<Compound:0xa1f2ac28>