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Identification
YMDB IDYMDB13273
NameLPA(14:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionLPA(14:0/0:0) 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(14:0/0:0), in particular, consists of one tetradecanoyl 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
SynonymsNot Available
CAS numberNot Available
WeightAverage: 382.434
Monoisotopic: 382.212040465
InChI KeyFAZBDRGXCKPVJU-UHFFFAOYSA-N
InChIInChI=1S/C17H35O7P/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/h16,18H,2-15H2,1H3,(H2,20,21,22)
IUPAC Name[2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name2-hydroxy-3-(tetradecanoyloxy)propoxyphosphonic acid
Chemical FormulaC17H35O7P
SMILESCCCCCCCCCCCCCC(=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 Solubility0.015 g/LALOGPS
logP3.11ALOGPS
logP4.07ChemAxon
logS-4.4ALOGPS
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 Count18ChemAxon
Refractivity95.78 m³·mol⁻¹ChemAxon
Polarizability42.94 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(14:0/14:0/14:0)PW007615 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:0/14:0/14:1(9Z))PW007625 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:0/14:0/15:0)PW007634 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:0/14:0/15:1(9Z))PW007640 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(14:0/14:0/16:0)PW007653 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
SpectraNot Available
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 ID89565
Kegg IDNot Available
ChemSpider ID80835
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available