Showing metabocard for LPA(18:0e/0:0) (BMDB0011144)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:13:32 UTC
Update Date2020-04-22 15:42:54 UTC
BMDB IDBMDB0011144
Secondary Accession Numbers
  • BMDB11144
Metabolite Identification
Common NameLPA(18:0e/0:0)
DescriptionLpa(18:0E/0:0), also known as lysopa(18:0E), belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond. Lpa(18:0E/0:0) is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lpa(18:0E/0:0) can be converted into 1-alkyl-2-acylglycerol 3 phosphate(18:0/20:4); which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha. In cattle, lpa(18:0E/0:0) is involved in the metabolic pathway called plasmalogen synthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Octadecyl-sn-glycero-3-phosphateHMDB
LysoPA(18:0E)HMDB
LysoPA(O-18:0)HMDB
PA(O-18:0/0:0)HMDB
[(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen phosphateHMDB
LPA(18:0E/0:0)HMDB
Chemical FormulaC21H45O6P
Average Molecular Weight424.559
Monoisotopic Molecular Weight424.295376167
IUPAC Name[2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid
Traditional Name2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O
InChI Identifier
InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25)
InChI KeyHUUYDUFSUADEJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct ParentMonoalkylglycerophosphates
Alternative Parents
Substituents
  • Monoalkylglycerophosphate
  • Monoalkyl phosphate
  • Glycerol ether
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP5.43ALOGPS
logP6.23ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity114.43 m³·mol⁻¹ChemAxon
Polarizability51.93 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 (1 TMS) - 70eV, Positivesplash10-03di-9470000000-767f506dcd3b43c89de4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6110900000-8f719fedcd8fb1e4993cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-0ea6133aa158799eba68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8f8d66131a6962c70022View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0000900000-ff350a6e4e4ad403170cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000100000-2f4e56c32a15bea85646View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2135900000-7c0ef85e3ad7588d5753View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi1-9476200000-0b62a2b23bd2c2bd072fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-8891000000-f8c957954f4425e7e3c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4105900000-6c1e7cdab36e3a134666View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9414200000-cd77a5ab324c3617b32aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9100000000-586af9b8586d3135a523View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011144
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB027919
KNApSAcK IDNot Available
Chemspider ID16017852
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10432493
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Lysophosphatidic acid receptor 1
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
Enzyme Details
2. Lysophosphatidic acid receptor 5
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