PA(20:4(5Z,8Z,11Z,14Z)e/2:0) (PAMDB000816)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000816
Identification
Name: PA(20:4(5Z,8Z,11Z,14Z)e/2:0)
Description:2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-phosphate is an 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.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-phosphate
  • 2-Acetyl-1-(5Z,8Z,11Z,14Z-eicosatetraenyl)-sn-glycero-phosphoric acid
  • PA(O-20:4(5Z,8Z,11Z,14Z)/2:0)
Chemical Formula: C25H43O7P
Average Molecular Weight: 486.5785
Monoisotopic Molecular Weight: 486.274640242
InChI Key: LTIFQHVEGFEXBJ-NTNVCBRRSA-N
InChI:InChI=1S/C25H43O7P/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-30-22-25(32-24(2)26)23-31-33(27,28)29/h7-8,10-11,13-14,16-17,25H,3-6,9,12,15,18-23H2,1-2H3,(H2,27,28,29)/b8-7-,11-10-,14-13-,17-16-/t25-/m1/s1
CAS number: Not Available
IUPAC Name:[(2R)-2-(acetyloxy)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propoxy]phosphonic acid
Traditional IUPAC Name: (2R)-2-(acetyloxy)-3-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraen-1-yloxy]propoxyphosphonic acid
SMILES:CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCCOC[C@]([H])(COP(=O)(O)O)OC(C)=O
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
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Acetate salt
  • Carboxylic acid ester
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00122 mg/mLALOGPS
logP5.89ALOGPS
logP6.11ChemAxon
logS-5.6ALOGPS
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 Count22ChemAxon
Refractivity137.25 m3·mol-1ChemAxon
Polarizability53.69 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, Positivesplash10-000i-2023900000-a72630bf21b2536ea9dbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fs-6596400000-3918cb7f5a23ce235785View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9375000000-49612d49a38d22fbf10dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0573-9110800000-f1bc93c0c8babccc089dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-0c97ef3e5ac867b2ba24View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-adc729c4a10121430b93View 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 IDHMDB11156
Pubchem Compound ID53480670
Kegg IDNot Available
ChemSpider ID24766522
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Transporters

Protein Details
• 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
Locus Tag:
PA4455
Molecular weight:
28.4 kDa