Record Information
Version1.0
Creation Date2016-09-30 23:45:48 UTC
Update Date2020-05-11 19:24:56 UTC
BMDB IDBMDB0007855
Secondary Accession Numbers
  • BMDB07855
Metabolite Identification
Common NameLPA(18:1(9Z)/0:0)
DescriptionPA(18:1(9Z)/0:0)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(18:1(9Z)/0:0), in particular, consists of two 9Z-octadecenoyl chain at positions C-1 and C2. 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
Synonyms
ValueSource
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphateChEBI
1-O-Oleoyl-sn-glycerol 3-phosphateChEBI
1-O-Oleyl-sn-glycerol 3-phosphateChEBI
1-Oleoyl lysophosphatidic acidChEBI
1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidic acidChEBI
1-Oleoyl-sn-glycero-3-phosphateChEBI
1-Oleoylglycerol 3-phosphateChEBI
1-Oleyl-2-lyso-sn-glycerol 3-phosphatidic acidChEBI
1-Oleyl-sn-glycerol 3-phosphateChEBI
1-Oleylglycerol 3-phosphateChEBI
1-Oleyllysophosphatidic acidChEBI
18:1 LPAChEBI
LPA 18:1ChEBI
LPA(18:1(9Z)/0:0)ChEBI
LPA(18:1)ChEBI
LPA(18:1/0:0)ChEBI
LPA(18:1n9/0:0)ChEBI
LPA(18:1W9/0:0)ChEBI
LysoPA(18:1(9Z)/0:0)ChEBI
LysoPA(18:1)ChEBI
LysoPA(18:1W9/0:0)ChEBI
Lysophosphatidic acid(18:1)ChEBI
Lysophosphatidic acid(18:1/0:0)ChEBI
Lysophosphatidic acid(18:1n9/0:0)ChEBI
Lysophosphatidic acid(18:1W9/0:0)ChEBI
Monooleylphosphatidic acidChEBI
PA(18:1/0:0)ChEBI
1-(9Z-Octadecenoyl)-sn-glycero-3-phosphoric acidGenerator
1-O-Oleoyl-sn-glycerol 3-phosphoric acidGenerator
1-O-Oleyl-sn-glycerol 3-phosphoric acidGenerator
1-Oleoyl lysophosphatidateGenerator
1-Oleoyl-2-lyso-sn-glycerol 3-phosphatidateGenerator
1-Oleoyl-sn-glycero-3-phosphoric acidGenerator
1-Oleoylglycerol 3-phosphoric acidGenerator
1-Oleyl-2-lyso-sn-glycerol 3-phosphatidateGenerator
1-Oleyl-sn-glycerol 3-phosphoric acidGenerator
1-Oleylglycerol 3-phosphoric acidGenerator
1-OleyllysophosphatidateGenerator
Lysophosphatidate(18:1)Generator
Lysophosphatidate(18:1/0:0)Generator
Lysophosphatidate(18:1n9/0:0)Generator
Lysophosphatidate(18:1W9/0:0)Generator
MonooleylphosphatidateGenerator
1-O-Oleyllysophosphatidic acidMeSH
9-Octadecenoic acid (9Z)-, 2-hydroxy-3-(phosphonooxy)propyl esterMeSH
1-Oleoyl-lyso-phosphatidic acidMeSH
Monooleylphosphatidic acid, sodium salt, (R)-isomerMeSH
1-Oleoyl-lysophosphatidic acidMeSH
LPA (lysophosphatidic acid)MeSH
Lysophosphatidic acidMeSH
Monooleylphosphatidic acid, (R)-isomerMeSH
MOPAMeSH
Chemical FormulaC21H41O7P
Average Molecular Weight436.5198
Monoisotopic Molecular Weight436.258990178
IUPAC Name[(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name1-oleoyl lysophosphatidic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@](O)([H])COP(O)(=O)O
InChI Identifier
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
InChI KeyWRGQSWVCFNIUNZ-GDCKJWNLSA-N
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
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.69ALOGPS
logP5.49ChemAxon
logS-5.4ALOGPS
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 Count21ChemAxon
Refractivity115.3 m³·mol⁻¹ChemAxon
Polarizability49.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-05n0-1664900000-148c650ac3bceb4b152cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ap0-3962100000-1a33e6ed4c6ff2881be4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0avr-7790000000-f51fa6e6693ad7c3d713View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01s9-4190400000-e613f5b69c617ba039f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-939e9b478cb01e4cdf3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5a4a918141c40ba8ca5dView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5311263
PDB IDNot Available
ChEBI ID62837
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in alkylglycerophosphoethanolamine phosphodies
Specific function:
Hydrolyzes lysophospholipids to produce the signaling molecule lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine (PubMed:12119361). Also can act on sphingosylphosphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor (By similarity). Required for LPA production in activated platelets, cleaves the sn-1 lysophospholipids to generate sn-1 lysophosphatidic acids containing predominantly 18:2 and 20:4 fatty acids (By similarity). Shows a preference for the sn-1 to the sn-2 isomer of 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) (By similarity).
Gene Name:
ENPP2
Uniprot ID:
A1A4K5
Molecular weight:
101717.0
General function:
Involved in G-protein coupled receptor protein signalin
Specific function:
Receptor for lysophosphatidic acid (LPA). Plays a role in the reorganization of the actin cytoskeleton, cell migration, differentiation and proliferation, and thereby contributes to the responses to tissue damage and infectious agents. Activates downstream signaling cascades via the G(i)/G(o), G(12)/G(13), and G(q) families of heteromeric G proteins. Signaling inhibits adenylyl cyclase activity and decreases cellular cAMP levels. Signaling triggers an increase of cytoplasmic Ca(2+) levels. Activates RALA; this leads to the activation of phospholipase C (PLC) and the formation of inositol 1,4,5-trisphosphate. Signaling mediates activation of down-stream MAP kinases. Contributes to the regulation of cell shape. Promotes Rho-dependent reorganization of the actin cytoskeleton in neuronal cells and neurite retraction. Promotes the activation of Rho and the formation of actin stress fibers. Promotes formation of lamellipodia at the leading edge of migrating cells via activation of RAC1. Through its function as lysophosphatidic acid receptor, plays a role in chemotaxis and cell migration, including responses to injury and wounding. Plays a role in triggering inflammation in response to bacterial lipopolysaccharide (LPS) via its interaction with CD14. Promotes cell proliferation in response to lysophosphatidic acid. Required for normal skeleton development. May play a role in osteoblast differentiation. Required for normal brain development. Required for normal proliferation, survival and maturation of newly formed neurons in the adult dentate gyrus. Plays a role in pain perception and in the initiation of neuropathic pain.
Gene Name:
LPAR1
Uniprot ID:
Q28031
Molecular weight:
41070.0
General function:
Involved in purinergic nucleotide receptor activity, G-
Specific function:
Receptor for lysophosphatidic acid (LPA), a mediator of diverse cellular activities.
Gene Name:
LPAR5
Uniprot ID:
Q3ZC80
Molecular weight:
40639.0