PA(12:0/16:1(9Z)) (YMDB01156)

Identification
YMDB IDYMDB01156
NamePA(12:0/16:1(9Z))
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionPA(12:0/16:1(9Z)) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(12:0/16:1(9Z)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl to the C-2 atom. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-dodecanoyl-2-(9Z-hexadecenoyl)-sn-phosphatidic acid
  • 1-dodecanoyl-2-palmitoleoyl-sn-glycero-3-phosphate
  • PA(12:0/16:1)
  • PA(12:0/16:1n7)
  • PA(12:0/16:1w7)
  • PA(28:1)
  • Phosphatidic Acid(12:0/16:1)
  • Phosphatidic Acid(12:0/16:1n7)
  • Phosphatidic Acid(12:0/16:1w7)
  • Phosphatidic Acid(28:1)
CAS numberNot Available
WeightAverage: 590.7691
Monoisotopic: 590.394755376
InChI KeyUARCTMUVJALMHM-FOIMXDHRSA-N
InChIInChI=1S/C31H59O8P/c1-3-5-7-9-11-13-14-15-16-18-20-22-24-26-31(33)39-29(28-38-40(34,35)36)27-37-30(32)25-23-21-19-17-12-10-8-6-4-2/h13-14,29H,3-12,15-28H2,1-2H3,(H2,34,35,36)/b14-13-/t29-/m1/s1
IUPAC Name[(2R)-3-(dodecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name(2R)-3-(dodecanoyloxy)-2-[(9Z)-hexadec-9-enoyloxy]propoxyphosphonic acid
Chemical FormulaC31H59O8P
SMILESCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • 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 Solubility0.00022 g/LALOGPS
logP7.59ALOGPS
logP9.74ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count31ChemAxon
Refractivity161.28 m³·mol⁻¹ChemAxon
Polarizability70.7 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Mitochondrion membrane
Organoleptic PropertiesNot Available
SMPDB Pathways
Cardiolipin Biosynthesis CL(12:0/16:1(9Z)/16:1(11Z)/16:1(11Z))PW007403 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:1(9Z)/16:1(11Z)/16:1(9Z))PW007404 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:1(9Z)/16:1(11Z)/18:0)PW007405 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:1(9Z)/16:1(11Z)/18:1(11Z))PW007406 ThumbThumb?image type=greyscaleThumb?image type=simple
Cardiolipin Biosynthesis CL(12:0/16:1(9Z)/16:1(11Z)/18:1(9Z))PW007407 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
143500 ± 16150 umol/L SD media with 2% raffinose24 oCBY4741PMID: 19174513
36000 ± 900 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 (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0020-0009900000-d28ff98fc0813bb4c9e8JSpectraViewer
References
References:
  • 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 IDNot Available
HMDB IDNot Available
Pubchem Compound ID52928640
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available