2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) (PAMDB001557)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001557
Identification
Name: 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1)
Description:2-Acyl-sn-glycero-3-phosphoglycerol (n-C14:1) belongs to the class of Lysophosphatidylglycerols. These are glycerophosphoglycerols (molecules containing a glycerol moiety attached to the phosphate group linked to a glycerol) in which only one fatty acid is bonded to the 1-glycerol moiety (through an ester linkage).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:Not Available
Chemical Formula: C20H38O9P
Average Molecular Weight: 453.4841
Monoisotopic Molecular Weight: 453.225344326
InChI Key: BHICCPXVDIQMCF-BQYQJAHWSA-M
InChI:InChI=1S/C20H39O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-20(24)29-19(15-22)17-28-30(25,26)27-16-18(23)14-21/h7-8,18-19,21-23H,2-6,9-17H2,1H3,(H,25,26)/p-1/b8-7+
CAS number: Not Available
IUPAC Name:1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl (7E)-tetradec-7-enoate
Traditional IUPAC Name: 1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl (7E)-tetradec-7-enoate
SMILES:[H]\C(CCCCCC)=C(\[H])CCCCCC(=O)OC(CO)COP([O-])(=O)OCC(O)CO
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as lysophosphatidylglycerols. These are glycerophosphoglycerols (molecules containing a glycerol moiety attached to the phosphate group linked to a glycerol) in which only one fatty acid is bonded to the 1-glycerol moiety (through an ester linkage).
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct Parent Lysophosphatidylglycerols
Alternative Parents
Substituents
  • Monoacylglycerophosphoglycerol
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.085 mg/mLALOGPS
logP2.67ALOGPS
logP2.76ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.58 Å2ChemAxon
Rotatable Bond Count21ChemAxon
Refractivity112.51 m3·mol-1ChemAxon
Polarizability48.71 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Adenosine triphosphate + Tetradecenoate (N-C14:1) > Adenosine monophosphate + PG(14:1(7Z)/14:1(7Z)) + Pyrophosphate
Water + PG(14:1(7Z)/14:1(7Z)) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Hydrogen ion + Tetradecenoate (N-C14:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + Water > Glycerophosphoglycerol + Hydrogen ion + Tetradecenoate (N-C14:1)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:1) + PG(14:1(7Z)/14:1(7Z)) > Acyl phosphatidylglycerol (N-C14:1) + Glycerophosphoglycerol
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-6210900000-65d6592a3a9333149439View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9330600000-eae6103f6221ee8cc882View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-68211949630a46e54f6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1120900000-9fd084ed8aeb1cbf8b49View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uk9-2930500000-d64f6b4725ef799f4211View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fur-9510000000-6faeb46d89a966bd9913View 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
  • 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 IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2134
EcoCyc IDCPD0-2134

Enzymes

Protein Details
• Lysophospholipase L2
General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Transporters