LPA(14:1(9Z)/0:0) (YMDB13276)

Identification
YMDB IDYMDB13276
NameLPA(14:1(9Z)/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLPA(14:1(9Z)/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(14:1(9Z)/0:0), in particular, consists of one 9Z-tetradecenoyl 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 380.418
Monoisotopic: 380.196390401
InChI KeyIQSHJASKBUVXAG-WAYWQWQTSA-N
InChIInChI=1S/C17H33O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(19)23-14-16(18)15-24-25(20,21)22/h5-6,16,18H,2-4,7-15H2,1H3,(H2,20,21,22)/b6-5-
IUPAC Name{2-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propoxy}phosphonic acid
Traditional IUPAC Name2-hydroxy-3-[(9Z)-tetradec-9-enoyloxy]propoxyphosphonic acid
Chemical FormulaC17H33O7P
SMILESCCCC\C=C/CCCCCCCC(=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 DescriptorsNot Available
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.042 g/LALOGPS
logP3.15ALOGPS
logP3.71ChemAxon
logS-4ALOGPS
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 Count17ChemAxon
Refractivity96.9 m³·mol⁻¹ChemAxon
Polarizability41.51 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolism TG(14:1(9Z)/15:0/15:1(9Z))PW007676 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:1(9Z)/15:0/16:0)PW007690 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:1(9Z)/15:0/16:1(9Z))PW007695 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:1(9Z)/15:1(9Z)/16:0)PW007696 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:1(9Z)/15:1(9Z)/16:1(9Z))PW007698 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot AvailableJSpectraViewer
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 ID87980420
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available