1-Lyso-2-arachidonoyl-phosphatidate (CHEM040924)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-27 01:04:57 UTC
Update Date2016-11-09 01:22:21 UTC
Accession NumberCHEM040924
Identification
Common Name1-Lyso-2-arachidonoyl-phosphatidate
ClassSmall Molecule
DescriptionLPA(0:0/20:4n6) 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. 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. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells.LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Lyso-2-arachidonoyl-phosphatidic acidGenerator
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphateHMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphate(2-)HMDB
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoric acidHMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoric acid(2-)HMDB
1-Lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-phosphatidic acidHMDB
2-all-cis-5,8,11,14-Eicosatetraenoyl-lysophosphatidic acidHMDB
2-Arachidonoyl-lysophosphatidic acidHMDB
2-Arachidonoyl-sn-glycero-3-phosphateHMDB
L-beta-Arachidonoyl-alpha-lysophosphatidic acidHMDB
[3-Hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonateHMDB
Chemical FormulaC23H37O7P
Average Molecular Mass456.509 g/mol
Monoisotopic Mass456.228 g/mol
CAS Registry NumberNot Available
IUPAC Name[3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonic acid
Traditional Name3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxyphosphonic acid
SMILESCCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O
InChI IdentifierInChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1
InChI KeyBDCFJMBXZCIVRH-NZRYSPDRSA-L
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent2-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 2-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0037 g/LALOGPS
logP4.97ALOGPS
logP5.29ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity127.85 m³·mol⁻¹ChemAxon
Polarizability49.14 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4000900000-819e2d5b9aaa86be40d0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9100000000-6307eb82a131f0391d31Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-7e1087b9c9e914081e89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-0229500000-aa32372cdeaa104ea519Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dr-2398000000-0d4ebdc1c1453eec2997Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-003v-9321000000-9e9c620862b97b08242cSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0012496
FooDB IDFDB029101
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider IDNot Available
ChEBI ID78209
PubChem Compound ID76043735
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18.
2. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89.
3. Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10.
4. Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3.
5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78.
6. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
7. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.
8. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.
9. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
10. Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15.
11. Phospholipids Handbook
12. The lipid handbook with CD-ROM