PC(14:0/18:0) (YMDB01812)

Identification

YMDB ID

YMDB01812

Name

PC(14:0/18:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PC(14:0/18:0) 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(14:0/18:0), in particular, consists of one tetradecanoyl 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

GPCho(14:0/18:0)
GPCho(32:0)
Lecithin
PC(14:0/18:0)
PC(32:0)
Phosphatidylcholine(14:0/18:0)
Phosphatidylcholine(32:0)
1-myristoyl-2-stearoyl-sn-glycero-3-phosphocholine
1-Tetradecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
GPCho(14:0/18:0)
Phosphatidylcholine(14:0/18:0)
1-Myristoyl-2-stearoylphosphatidylcholine
1m-2S-PC
GPCho(32:0)
Lecithin
Phosphatidylcholine(32:0)
PC(32:0)
PC(14:0/18:0)

CAS number

Not Available

Weight

Average: 734.0389
Monoisotopic: 733.562155053

InChI Key

TYAQXZHDAGZOEO-KXQOOQHDSA-N

InChI

InChI=1S/C40H80NO8P/c1-6-8-10-12-14-16-18-19-20-21-23-25-27-29-31-33-40(43)49-38(37-48-50(44,45)47-35-34-41(3,4)5)36-46-39(42)32-30-28-26-24-22-17-15-13-11-9-7-2/h38H,6-37H2,1-5H3/t38-/m1/s1

IUPAC Name

trimethyl(2-{[(2R)-2-(octadecanoyloxy)-3-(tetradecanoyloxy)propyl phosphonato]oxy}ethyl)azanium

Traditional IUPAC Name

lecithin

Chemical Formula

C₄₀H₈₀NO₈P

SMILES

[H][C@@](COC(=O)CCCCCCCCCCCCC)(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 32:0 (CHEBI:86090 )
Diacylglycerophosphocholines (LMGP01010488 )

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	2.4e-05 g/L	ALOGPS
logP	5.3	ALOGPS
logP	8.11	ChemAxon
logS	-7.5	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	40	ChemAxon
Refractivity	215.87 m³·mol⁻¹	ChemAxon
Polarizability	91.3 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

Phosphatidylcholine biosynthesis PC(14:0/18:0)

PW002911

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
0.067 ± 0.00335 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	splash10-10t9-0000695200-03cf9384d9642c1b2326	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0560-0090000200-7ad75eecb893ceb9e068	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0190001000-d0b1f2221d88b3ff8b87	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-4190000000-3515708f7006ee6b7464	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000900-5e10f1a30c4d50bef4d5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-0090012600-4f6d43bf878bf7cee89a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-2192000000-ff9b00f4b28c18855ded	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0000000900-6e9649493c42be4c2576	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0000001900-5df0d0c4d9ec6f9682a0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-0600491100-d83e52f26583665011df	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000900-e5d71c7fe9aceaf67e2c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0600000900-72d36726311f0fc83bdc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-1900231200-6f7a6f77a74dcb2a15dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-cd7e68f0df8f8474d7ce	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014i-0030000900-282a21f4f66799410334	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ai-0090000400-fb7d403fec7aacc820de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000900-37dbd3a8158d1e1870de	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000001900-c7043b2875ba9f704d15	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a59-0101491100-3ad75f057db8913ec1ad	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:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	86090
HMDB ID	HMDB07871
Pubchem Compound ID	131150
Kegg ID	C00157
ChemSpider ID	115945
FOODB ID	FDB025063
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xa4a96f74>