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Identification
YMDB IDYMDB13365
NameLyso-PS(0:0/14:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLyso-PS(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-PS(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. Lysophosphatidylserines (LPSs) enhance glucose transport, lowering blood glucose levels while leaving secretion of insulin unaffected. LPSs have been known as a signaling phospholipid in mast cell biology. They enhance stimulated histamine release and eicosanoid production. LPSs also play a roles in the promotion of phagocytosis of apoptotic cells and resolution of inflammation.
Structure
Thumb
SynonymsNot Available
CAS numberNot Available
WeightAverage: 468.504
Monoisotopic: 468.236792418
InChI KeyTZPRMIGZGQOWBD-UHFFFAOYSA-M
InChIInChI=1S/C20H40NO9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-19(23)30-17(14-22)15-28-31(26,27)29-16-18(21)20(24)25/h17-18,22H,2-16,21H2,1H3,(H,24,25)(H,26,27)/p-1
IUPAC Name2-azaniumyl-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate
Traditional IUPAC Name2-ammonio-3-{[3-hydroxy-2-(tetradecanoyloxy)propyl phosphono]oxy}propanoate
Chemical FormulaC20H39NO9P
SMILESCCCCCCCCCCCCCC(=O)OC(CO)COP([O-])(=O)OCC([NH3+])C([O-])=O
Chemical Taxonomy
Physical Properties
StateSolid
Charge-1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0061 g/LALOGPS
logP2.7ALOGPS
logP1.68ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)9.38ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area172.89 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity135.05 m³·mol⁻¹ChemAxon
Polarizability50.64 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
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
Lyso-PS(0:0/14:0) + Adenosine triphosphate + waterLyso-PS(0:0/14:0) + ADP + phosphate
Lyso-PS(0:0/14:0) + Adenosine triphosphate + waterLyso-PS(0:0/14:0) + ADP + phosphate
Lyso-PS(0:0/14:0)PS(14:0/14:0)
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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).