Record Information
Version3.6
Creation Date2008-10-29 14:20:21 UTC
Update Date2013-02-09 00:25:46 UTC
HMDB IDHMDB11144
Secondary Accession NumbersNone
Metabolite Identification
Common 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.
Structure
Thumb
Synonyms
  1. 1-Octadecyl-sn-glycero-3-phosphate
  2. LysoPA(18:0e)
  3. LysoPA(O-18:0)
  4. PA(O-18:0/0:0)
  5. [(2R)-2-hydroxy-3-octadecoxy-propyl] dihydrogen phosphate
Chemical FormulaC21H45O6P
Average Molecular Weight424.5522
Monoisotopic Molecular Weight424.295375684
IUPAC Name[(2R)-2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid
Traditional IUPAC Name(2R)-2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COCCCCCCCCCCCCCCCCCC)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)/t21-/m1/s1
InChI KeyHUUYDUFSUADEJQ-OAQYLSRUSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Monoalkylglycerophosphates(Lipidmaps)
Substituents
  • Dialkyl Ether
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct ParentMonoalk(en)ylglycerophosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
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 area96.22ChemAxon
rotatable bond count22ChemAxon
refractivity114.43ChemAxon
polarizability51.55ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Plasmalogen SynthesisSMP00479Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB027919
KNApSAcK IDNot Available
Chemspider ID8607920
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB11144
Metagene LinkHMDB11144
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

Gene Name:
PPAP2C
Uniprot ID:
O43688
Gene Name:
PPAP2A
Uniprot ID:
O14494
Gene Name:
PPAP2B
Uniprot ID:
O14495
Gene Name:
PTK2
Uniprot ID:
Q05397
Gene Name:
PTK2B
Uniprot ID:
Q14289
Gene Name:
LPAR2
Uniprot ID:
Q9HBW0
Gene Name:
LPAR1
Uniprot ID:
Q92633
Gene Name:
AGPAT6
Uniprot ID:
Q86UL3
Gene Name:
LCLAT1
Uniprot ID:
Q6UWP7
Gene Name:
LPAR3
Uniprot ID:
Q9UBY5
Gene Name:
LPAR4
Uniprot ID:
Q99677
Gene Name:
LPAR5
Uniprot ID:
Q9H1C0
Gene Name:
LPCAT4
Uniprot ID:
Q643R3
Gene Name:
AGPAT9
Uniprot ID:
Q53EU6
Gene Name:
LPAR6
Uniprot ID:
P43657
Gene Name:
LIPH
Uniprot ID:
Q8WWY8
Gene Name:
LIPI
Uniprot ID:
Q6XZB0
Gene Name:
AGK
Uniprot ID:
Q53H12
Gene Name:
LPAR1
Uniprot ID:
B1AP63
Gene Name:
LPAR1
Uniprot ID:
Q6GPG7