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LPA(16:0/0:0) (YMDB00259)

Identification
YMDB IDYMDB00259
NameLPA(16:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLPA(16:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(16:0/0:0), in particular, consists of one hexadecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-hexadecanoyl-phosphatidic acid
  • 1-Palmitoyl lysophosphatidate
  • 1-Palmitoyl lysophosphatidic acid
  • 1-palmitoyl-glycero-3-phosphate
  • 1-Palmitoylglycerol 3-phosphate
  • 1-Palmitoyllysophosphatidate
  • 1-Palmitoyllysophosphatidic acid
  • 1,2-Diacyl-sn-glycerol 3-phosphate
  • 2-hydroxy-3-(phosphonooxy)propyl ester Hexadecanoate
  • 2-hydroxy-3-(phosphonooxy)propyl ester Hexadecanoic acid
  • 3-sn-Phosphatidate
  • LPA(16:0)
  • LPA(16:0/0:0)
  • LysoPA(16:0/0:0)
  • Lysophosphatidic acid(16:0)
  • Lysophosphatidic acid(16:0/0:0)
  • Phosphatidate
  • Phosphatidic acid
  • phosphatidic acids
  • 1-Hexadecanoyl-sn-glycero-3-phosphate
  • 1-Hexadecanoyl-sn-glycero-3-phosphoric acid
  • 1-Palmitoylglycerol 3-phosphoric acid
  • 1-Palmitoyl-sn-glycerol 3-phosphate
  • PLPA
  • 1-Palmitoyl-lysophosphatidic acid
  • 1-Palmitoyl-lysophosphatidic acid, (R)-isomer
  • 1-Palmitoyl-rac-glycerol 3-phosphate
  • 1-Palmitoyl-lysophosphatidic acid, sodium salt, (R)-isomer
  • 1-Hexadecanoyl-glycero-3-phosphate
CAS numberNot Available
WeightAverage: 410.4825
Monoisotopic: 410.243340114
InChI KeyYNDYKPRNFWPPFU-UHFFFAOYSA-N
InChIInChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)
IUPAC Name[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC NamePLPA
Chemical FormulaC19H39O7P
SMILESCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • 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 Solubility0.0024 g/LALOGPS
logP3.87ALOGPS
logP4.96ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.98 m³·mol⁻¹ChemAxon
Polarizability47.18 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin BiosynthesisPW002431 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/28:0)PW003484 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/10:0/30:0)PW003501 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/26:0)PW003502 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(10:0/10:0/12:0/28:0)PW003503 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerolipid metabolismec00561 Map00561
Glycerophospholipid metabolismec00564 Map00564
SMPDB ReactionsNot Available
KEGG Reactions
acyl-CoA + PA(18:1(9Z)/0:0) ↔ hydron + LPA(16:0/0:0) + Coenzyme A
LPA(16:0/0:0) + hydron + Cytidine triphosphate ↔ Pyrophosphate + CDP-diacylglycerol
LPA(16:0/0:0) + water ↔ DG(16:0/16:0/0:0) + phosphate + hydron
water + 1,2-diacylglycerol 3-diphosphate → LPA(16:0/0:0) + phosphate + hydron
phosphatidylcholine + water → LPA(16:0/0:0) + Choline
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
32500 ± 8700 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
52750 ± 1900 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02n9-5940100000-a5ca92d33fddeb085287JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - NA , positivesplash10-03di-0549600000-25838221a69792238ab5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-2986700000-f3b30f5c39843042fd11JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-3942000000-0e96d3c410d5f67cbc44JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-6930000000-8e619c799b8a218b3a05JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-4190300000-bb83e3f01055cbe6102fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-de299cedb3cf89da4492JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f3fc94f808e80bf00353JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000900000-97431642e54a4a707394JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000900000-97431642e54a4a707394JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2951500000-d6189b2a977487b10d88JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000900000-61bb60154e9d7308c06dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0000900000-61bb60154e9d7308c06dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-0955100000-a47b051136d1c4973480JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • 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 ID15799
HMDB IDHMDB07853
Pubchem Compound ID89565
Kegg IDC00416
ChemSpider ID4925335
FOODB IDFDB030254
WikipediaLecithin
BioCyc IDL-PHOSPHATIDATE

Enzymes

Protein Details
1. NADPH-dependent 1-acyldihydroxyacetone phosphate reductase
General function:
Involved in oxidoreductase activity
Specific function:
Can convert acyl and alkyl dihydroxyacetone-phosphate (DHAP) into glycerolipids and ether lipids, respectively. Required for the biosynthesis of phosphatidic acid via the DHAP pathway, where it reduces 1-acyl DHAP to lysophosphatidic acid (LPA). Required for spore germination
Gene Name:
AYR1
Uniprot ID:
P40471
Molecular weight:
32813.60156
Reactions
1-palmitoylglycerol 3-phosphate + NADP(+) → palmitoylglycerone phosphate + NADPH.