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Identification
YMDB IDYMDB01184
NamePC(16:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLysoPC(16:1(9Z)) 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(16:1(9Z)), in particular, consists of one chain of palmitoleic acid at the C-1 position. 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
Thumb
Synonyms
  • 1-(9Z-octadecenoyl)-sn-glycero-3-phosphocholine
  • 1-acyl-2-lyso-phosphatidylcholine
  • 1-Acyl-sn-glycero-3-phosphocholine
  • 1-acyl-sn-glycero-3-phosphocholines
  • 1-Acyl-sn-glycerol-3-phosphocholine
  • 1-Acylglycerophosphocholine
  • 1-Oleoyl-sn-glycero-3-phosphocholine
  • 1-Oleoylglycerophosphocholine
  • 1-palmitoleoyl-glycero-3-phosphocholine
  • 2-Lysolecithin
  • 2-Lysophosphatidylcholine
  • 3-Oleoyl-rac-glycerol-1-phosphorylcholine
  • alpha-Acylglycerophosphocholine
  • Choline phosphate (ester) 3-ester with 1-monoolein
  • Choline phosphate 3-ester with 1-monoolein
  • GPCho(18:1(9Z)/0:0)[rac]
  • LPC
  • LPC(16:1)
  • LPC(16:1/0:0)
  • LPC(16:1n7/0:0)
  • LPC(16:1w7/0:0)
  • LyPC(16:1)
  • LyPC(16:1/0:0)
  • LyPC(16:1n7/0:0)
  • LyPC(16:1w7/0:0)
  • LysoPC(16:1)
  • LysoPC(16:1/0:0)
  • LysoPC(16:1n7/0:0)
  • LysoPC(16:1w7/0:0)
  • LysoPC(18:1)
  • Lysophosphatidylcholine(16:1)
  • Lysophosphatidylcholine(16:1/0:0)
  • Lysophosphatidylcholine(16:1n7/0:0)
  • Lysophosphatidylcholine(16:1w7/0:0)
  • Lysophosphatidylcholine(18:1)
  • Lysophosphatidylcholine(18:1/0:0)
  • Lysophosphatidylcholine(18:1n9/0:0)
  • Lysophosphatidylcholine(18:1w9/0:0)
  • LysoPIC(18:1/0:0)
  • Olein-1-mono-3-phosphate ester with choline
  • Oleoyl lysolecithin
  • Oleoyl lysophosphatidylcholine
  • 1-(9Z-Hexadecenoyl)-sn-glycero-3-phosphocholine
  • 1-Palmitoleoyl-glycerophosphocholine
  • 1-Palmitoleoyl-GPC
  • GPC(16:1(9Z))
  • GPC(16:1)
  • LPC 16:1(9Z)/0:0
  • LPC(16:1(9Z)/0:0)
  • LysoPC 16:1(9Z)/0:0
  • LysoPC(16:1(9Z)/0:0)
  • Lysophosphatidylcholine(16:1(9Z)/0:0)
  • PC 16:1(9Z)/0:0
  • PC(16:1(9Z)/0:0)
  • LysoPC a C16:1
  • LysoPC(16:1(9Z))
  • 1-(9Z-hexadecenoyl)-glycero-3-phosphocholine
CAS numberNot Available
WeightAverage: 493.6142
Monoisotopic: 493.316839407
InChI KeyLFUDDCMNKWEORN-ZXEGGCGDSA-N
InChIInChI=1S/C24H48NO7P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-24(27)30-21-23(26)22-32-33(28,29)31-20-19-25(2,3)4/h10-11,23,26H,5-9,12-22H2,1-4H3/b11-10-/t23-/m1/s1
IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Traditional IUPAC Name(2-{[(2R)-3-[(9Z)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphonato]oxy}ethyl)trimethylazanium
Chemical FormulaC24H48NO7P
SMILESCCCCCC\C=C/CCCCCCCC(=O)OC[C@@]([H])(O)COP([O-])(=O)OCC[N+](C)(C)C
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct Parent1-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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.00043 g/LALOGPS
logP1.72ALOGPS
logP0.83ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)1.86ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area105.12 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity143.39 m³·mol⁻¹ChemAxon
Polarizability56.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic reticulum
  • Mitochondria
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ER PC(16:1(9Z)/16:1(9Z))PW002785 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(16:1(9Z)/16:1(9Z))PW002793 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
PC(16:1(9Z)/0:0) + waterGlycerophosphocholine + a carboxylate
PC(16:1(9Z)/0:0)PC(16:1(9Z)/16:1(9Z))
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
0.443 ± 0.02215 µM YEB media with 0.5 mM glucoseaerobicBrewer's yeastExperimentally Determined
Not Available
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
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:
ResourceLink
CHEBI ID73851
HMDB IDHMDB0010383
Pubchem Compound ID24779461
Kegg IDC04230
ChemSpider ID24766525
FOODB IDFDB027534
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in metabolic process
Specific function:
Intracellular phospholipase B that catalyzes the double deacylation of phosphatidylcholine (PC) to glycerophosphocholine (GroPCho). Plays an important role in membrane lipid homeostasis. Responsible for the rapid PC turnover in response to inositol, elevated temperatures, or when choline is present in the growth medium
Gene Name:
NTE1
Uniprot ID:
Q04958
Molecular weight:
187131.0
Reactions
2-lysophosphatidylcholine + H(2)O → glycerophosphocholine + a carboxylate.