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Identification
YMDB IDYMDB13347
NameLyso-PI(0:0/14:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLyso-PI(0:0/14:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PI(0:0/14:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylinositol is an endogenous lysophospholipid and endocannabinoid neurotransmitter.
Structure
Thumb
SynonymsNot Available
CAS numberNot Available
WeightAverage: 544.575
Monoisotopic: 544.264863887
InChI KeyKJKJVATVGMLDCK-UHFFFAOYSA-N
InChIInChI=1S/C23H45O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(25)34-16(14-24)15-33-36(31,32)35-23-21(29)19(27)18(26)20(28)22(23)30/h16,18-24,26-30H,2-15H2,1H3,(H,31,32)
IUPAC Name[3-hydroxy-2-(tetradecanoyloxy)propoxy][(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid
Traditional IUPAC Name3-hydroxy-2-(tetradecanoyloxy)propoxy((2,3,4,5,6-pentahydroxycyclohexyl)oxy)phosphinic acid
Chemical FormulaC23H45O12P
SMILESCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(=O)OC1C(O)C(O)C(O)C(O)C1O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acyl-sn-glycerol-3-phosphoinositols. These are glycerophosphoinositols where the glycerol is acylated only at position O-2 with a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct Parent2-acyl-sn-glycerol-3-phosphoinositols
Alternative Parents
Substituents
  • 2-acyl-sn-glycerol-3-phosphoinositol
  • Inositol phosphate
  • Cyclohexanol
  • Fatty acid ester
  • Dialkyl phosphate
  • Cyclitol or derivatives
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.11 g/LALOGPS
logP1.59ALOGPS
logP1.18ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity127.77 m³·mol⁻¹ChemAxon
Polarizability57.9 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Lysolipid incorporation into ERPW002532 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(14:0/14:0)PW002783 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into MitochondriaPW002531 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into Mitochondria PC(14:0/14:0)PW002792 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB Reactions
Adenosine triphosphate + water + Lyso-PI(0:0/14:0)ADP + phosphate + Lyso-PI(0:0/14:0)
Adenosine triphosphate + water + Lyso-PI(0:0/14:0)ADP + phosphate + Lyso-PI(0:0/14:0)
Lyso-PI(0:0/14:0)PI(14:0/14:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03fs-1596060000-87d3929ca160d2387da2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0400-3493010000-a591be4d92a91b2385beJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fv-7920000000-0a250f808c2b5d950a24JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-0096080000-d7a7dfe1d82244005e58JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-056r-7393020000-e86de1ed700eee1cc27fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9130000000-08ef190933a01f1df00aJSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Transporters

General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids. Required for protein transport from Golgi to vacuoles
Gene Name:
DNF2
Uniprot ID:
Q12675
Molecular weight:
182617.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).
General function:
Involved in nucleotide binding
Specific function:
This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids (Potential)
Gene Name:
DNF1
Uniprot ID:
P32660
Molecular weight:
177796.0
Reactions
ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).