PA(16:0e/18:0) (PAMDB000814)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000814
Identification
Name: PA(16:0e/18:0)
Description:2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is an intermediate in ether lipid metabolism. 2-octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate is converted from 1-octadecyl-glycerone-3-phosphate via 1-acylglycerol-3-phosphate O-acyltransferase. (EC: 2.3.1.51) 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. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked bilayers.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphate
  • 2-Octadecanoyl-1-hexadecyl-sn-glycero-3-phosphoric acid
  • PA(O-16:0/18:0)
Chemical Formula: C37H75O7P
Average Molecular Weight: 662.961
Monoisotopic Molecular Weight: 662.525041266
InChI Key: BIMPCBJDAYKNLD-PSXMRANNSA-N
InChI:InChI=1S/C37H75O7P/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-37(38)44-36(35-43-45(39,40)41)34-42-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h36H,3-35H2,1-2H3,(H2,39,40,41)/t36-/m1/s1
CAS number: Not Available
IUPAC Name:[(2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name: (2R)-3-(hexadecyloxy)-2-(octadecanoyloxy)propoxyphosphonic acid
SMILES:[H][C@@](COCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1-alkyl,2-acylglycerophosphates. These are glycerophosphates in which the O-1 atom of the glycerol is bonded to a fatty acid (saturated or unsaturated) through an ether linkage, and the O-2 atom is bonded to another fatty acid through an ester linkage.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphates
Direct Parent 1-alkyl,2-acylglycerophosphates
Alternative Parents
Substituents
  • 1-alkyl,2-acyl-glycerol-3-phosphate
  • Monoalkyl phosphate
  • Glycerol ether
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.4e-05 mg/mLALOGPS
logP9.4ALOGPS
logP13.15ChemAxon
logS-6.9ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area102.29 Å2ChemAxon
Rotatable Bond Count38ChemAxon
Refractivity188.02 m3·mol-1ChemAxon
Polarizability84.19 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02vj-0095035000-abc1e4ed109c621aad65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00os-1092021000-dfd123715459896c106bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mt-1290020000-6064c23505566aa5059fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01u1-7196106000-8d7ebe09b68b4da24a2eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9020000000-316de4578cc6c723846aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-673edd9596ecce23c64fView in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.A
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB11145
Pubchem Compound ID52929644
Kegg IDNot Available
ChemSpider ID24766519
Wikipedia IDNot Available
BioCyc IDNot Available