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PA(16:0e/18:0) (M2MDB000814)

Record Information
Version2.0
Creation Date2012-05-31 14:20:17 -0600
Update Date2015-06-03 17:19:01 -0600
Secondary Accession Numbers
  • ECMDB11145
Identification
Name:PA(16:0e/18:0)
Description2-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 662.961
Monoisotopic: 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
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-alkyl,2-acylglycerophosphates
Alternative Parents
Substituents
  • 1-alkyl,2-acyl-glycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Glycerol ether
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.4e-05 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity188.02 m³·mol⁻¹ChemAxon
Polarizability84.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9362652000-e3c1e1e26c9d0956f777View in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1031293000-5835d0fa74d0a96f2017View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-030a-9111583000-3ab27336202728521d55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-1985100000-406509471bc80dee7a37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1000009000-7ebcbed37497909d70bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9000001000-6ceb500438606d761db0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004j-9010000000-c1d1f1fe9603beb34469View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

Protein Details
1. 1-acyl-sn-glycerol-3-phosphate acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsC
Uniprot ID:
P26647
Molecular weight:
27453
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1,2-diacyl-sn-glycerol 3-phosphate.
Protein Details
2. Protein crcA
General function:
Not Available
Specific function:
Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:
crcA
Uniprot ID:
P37001
Molecular weight:
21770

Transporters

Protein Details
1. Probable phospholipid ABC transporter-binding protein mlaB
General function:
Involved in phospholipid transporter activity
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaB
Uniprot ID:
P64602
Molecular weight:
10680
Protein Details
2. Probable phospholipid ABC transporter-binding protein mlaD
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaD
Uniprot ID:
P64604
Molecular weight:
19576
Protein Details
3. Probable phospholipid ABC transporter permease protein mlaE
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
mlaE
Uniprot ID:
P64606
Molecular weight:
27863