LysoPC(18:1(11Z)) (YMDB02211)

Identification

YMDB ID

YMDB02211

Name

LysoPC(18:1(11Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

LysoPC(18:1(11Z)) is a lysophospholipid (LyP). It is a monoglycerophospholipid in which a phosphorylcholine moiety occupies a glycerol substitution site. Lysophosphatidylcholines can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) position. Fatty acids containing 16, 18 and 20 carbons are the most common. LysoPC(18:1(11Z)), in particular, consists of one chain of vaccenic acid at the C-1 position. The vaccenic acid moiety is derived from butter fat and animal fat. Lysophosphatidylcholine is found in small amounts in most tissues. It is formed by hydrolysis of phosphatidylcholine by the enzyme phospholipase A2, as part of the de-acylation/re-acylation cycle that controls its overall molecular species composition. It can also be formed inadvertently during extraction of lipids from tissues if the phospholipase is activated by careless handling.

Structure

MOL SDF PDB SMILES InChI

Synonyms

1-vaccenoyl-glycero-3-phosphocholine
LPC(18:1)
LPC(18:1/0:0)
LPC(18:1n7/0:0)
LPC(18:1w7/0:0)
LyPC(18:1)
LyPC(18:1/0:0)
LyPC(18:1n7/0:0)
LyPC(18:1w7/0:0)
LysoPC(18:1)
LysoPC(18:1/0:0)
LysoPC(18:1n7/0:0)
LysoPC(18:1w7/0:0)
Lysophosphatidylcholine(18:1)
Lysophosphatidylcholine(18:1n7/0:0)
Lysophosphatidylcholine(18:1w7/0:0)
Lysophosphatidylcholine(18:1/0:0)
1-Vaccenoyl-glycero-3-phosphocholine
LPC(18:1)
LysoPC(18:1(11Z))
LysoPC(18:1)
Lysophosphatidylcholine(18:1)
PC 18:1(11Z)/0:0
PC(18:1(11Z)/0:0)
LPC(18:1/0:0)
LPC(18:1n7/0:0)
LPC(18:1W7/0:0)
LyPC(18:1)
LyPC(18:1/0:0)
LyPC(18:1n7/0:0)
LyPC(18:1W7/0:0)
LysoPC a C18:1
LysoPC(18:1/0:0)
LysoPC(18:1n7/0:0)
LysoPC(18:1W7/0:0)
Lysophosphatidylcholine(18:1n7/0:0)
Lysophosphatidylcholine(18:1W7/0:0)
1-(11Z-Octadecenoyl)-glycero-3-phosphocholine
1-Vaccenoylglycerophosphocholine

CAS number

Not Available

Weight

Average: 521.6673
Monoisotopic: 521.348139535

InChI Key

PZRFVAHZNWPPAC-RUZDIDTESA-N

InChI

InChI=1S/C26H52NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-26(29)32-23-25(28)24-34-35(30,31)33-22-21-27(2,3)4/h10-11,25,28H,5-9,12-24H2,1-4H3/t25-/m1/s1

IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Traditional IUPAC Name

(2-{[(2R)-2-hydroxy-3-[(11Z)-octadec-11-enoyloxy]propyl phosphono]oxy}ethyl)trimethylazanium

Chemical Formula

C₂₆H₅₂NO₇P

SMILES

CCCCCCC=CCCCCCCCCCC(=O)OC[C@@H](O)COP([O-])(=O)OCC[N+](C)(C)C

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-acyl-sn-glycero-3-phosphocholines. These are glycerophosphocholines in which the glycerol is esterified with a fatty acid at O-1 position, and linked at position 3 to a phosphocholine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphocholines

Direct Parent

1-acyl-sn-glycero-3-phosphocholines

Alternative Parents

Substituents

1-acyl-sn-glycero-3-phosphocholine
Phosphocholine
Fatty acid ester
Dialkyl phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Tetraalkylammonium salt
Quaternary ammonium salt
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Organic oxygen compound
Organopnictogen compound
Carbonyl group
Organic salt
Amine
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-O-acyl-sn-glycero-3-phosphocholine (CHEBI:86255 )
lysophosphatidylcholine 18:1 (CHEBI:86255 )

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	0.00028 g/L	ALOGPS
logP	2.38	ALOGPS
logP	1.72	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	1.86	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	105.12 Å²	ChemAxon
Rotatable Bond Count	25	ChemAxon
Refractivity	152.59 m³·mol⁻¹	ChemAxon
Polarizability	60.46 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
0.132 ± 0.0066 µM	YEB media with 0.5 mM glucose	aerobic	Brewer's yeast	Experimentally Determined Not Available
319250 ± 27975 umol/L	SD media with 2% raffinose	24 oC	BY4741	PMID: 19174513
3500 ± 650 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 GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-007t-5950100000-d2d627f1bf5f98609109	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-024u-9431010000-e487b14464af3dc739a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9162130000-aa9b8b51c78b1b8d1753	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kr-8393000000-14b298ea6483402da89f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-9140000000-fbca67ff1ab00ebfc5bc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01x0-0090030000-706190fb31fd956d11ed	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-0090100000-6d76540b1efe6814b7b0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01si-5190000000-95de222a575d1763b1f1	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0000190000-37dcc74901c1425d0392	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0190-0002990000-c8110d0a5e4476020596	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0frj-0309400000-cd464845573077fb0e9f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0030090000-c08a294df5c170ac8b76	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-1090010000-3f3fbc869926a73a5b72	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090000000-1894b105723e28dacec8	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000090000-f6a072a97b578a3bd0b0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-0090070000-f56fc89aebf13639f1ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-0090020000-be75beb7bf742731dc1e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000190000-ed1ce66db5beed8bfab7	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000l-0001960000-b2d5105862a37356da93	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gw0-1609710000-4adbedbb1f89568d7285	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0fk9-0000090000-382efaabb1329b98f1ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0089-0900060000-7d4d5ee776e7a08537ae	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ue9-0910040000-b15364334c9b09b73db5	JSpectraViewer

References

References:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	86255
HMDB ID	HMDB10385
Pubchem Compound ID	53480465
Kegg ID	C04230
ChemSpider ID	24766526
FOODB ID	FDB027536
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xaca2f984>