Record Information
Version1.0
Creation date2011-09-21 01:32:00 UTC
Update date2015-07-21 06:59:16 UTC
Primary IDFDB027919
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLPA(18:0e/0:0)
Description1-Octadecyl-sn-glycero-3-phosphate is a lysophosphatidyl ether lipid. Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. The formation of the ether bond in mammals requires two enzymes, dihydoxyacetonephosphate acyltransferase (DHAPAT) and alkyldihydroxyacetonephosphate synthase (ADAPS), that reside in the peroxisome. [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
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
[(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen ateHMDB
[(2R)-2-hydroxy-3-octadecoxy-propyl] dihydrogen phosphatehmdb
1-Octadecyl-sn-glycero-3-ateHMDB
LysoPA(18:0e)hmdb
LysoPA(o-18:0)hmdb
PA(o-18:0/0:0)hmdb
Predicted Properties
PropertyValueSource
Water Solubility0.0024 g/LALOGPS
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
Polarizability51.55 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC21H45O6P
IUPAC name[(2R)-2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid
InChI IdentifierInChI=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)/t21-/m1/s1
InChI KeyHUUYDUFSUADEJQ-OAQYLSRUSA-N
Isomeric SMILES[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)COP(O)(O)=O
Average Molecular Weight424.5522
Monoisotopic Molecular Weight424.295375684
Classification
Description Belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphocholines
Direct ParentPhosphatidylcholines
Alternative Parents
Substituents
  • Diacylglycero-3-phosphocholine
  • Phosphocholine
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSLPA(18:0e/0:0), non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ot-9740000000-0bddbbcc16ee2e885ab1Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2135900000-7c0ef85e3ad7588d5753Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zi1-9476200000-0b62a2b23bd2c2bd072fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-8891000000-f8c957954f4425e7e3c4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6110900000-8f719fedcd8fb1e4993cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-0ea6133aa158799eba68Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8f8d66131a6962c70022Spectrum
NMRNot Available
ChemSpider ID8607920
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10432493
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB11144
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycerol-3-phosphate acyltransferase 3AGPAT9Q53EU6
Lysophosphatidic acid phosphatase type 6ACP6Q9NPH0
Lysophosphatidic acid receptor 2LPAR2Q9HBW0
Lipid phosphate phosphatase-related protein type 4LPPR4Q7Z2D5
Glycerol-3-phosphate acyltransferase 4AGPAT6Q86UL3
Focal adhesion kinase 1PTK2Q05397
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
1-acyl-sn-glycerol-3-phosphate acyltransferase gammaAGPAT3Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase betaAGPAT2O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alphaAGPAT1Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilonAGPAT5Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase deltaAGPAT4Q9NRZ5
Lysocardiolipin acyltransferase 1LCLAT1Q6UWP7
Lysophospholipid acyltransferase LPCAT4LPCAT4Q643R3
Acyl-CoA:lysophosphatidylglycerol acyltransferase 1LPGAT1Q92604
Lysophosphatidic acid receptor 1LPAR1Q92633
Lysophosphatidic acid receptor 3LPAR3Q9UBY5
Lysophosphatidic acid receptor 5LPAR5Q9H1C0
Pathways
NameSMPDB LinkKEGG Link
Plasmalogen SynthesisSMP00479 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference