2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) (ECMDB21147) (M2MDB001556)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (3)Transporters (1)XML
Proteins (4)
Record Information
Version2.0
Creation Date2012-07-30 14:54:41 -0600
Update Date2015-06-03 17:20:44 -0600
Secondary Accession Numbers
  • ECMDB21147
Identification
Name:2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0)
Description2-acyl-sn-glycero-3-phosphoglycerol (n-c14:0) 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
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-14:0-Lysophosphatidylglycerol
  • 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0)
Chemical Formula:C20H40O9P
Weight:Average: 455.5
Monoisotopic: 455.24099439
InChI Key:NHYJQQUDLXESED-UHFFFAOYSA-M
InChI:InChI=1S/C20H41O9P/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/h18-19,21-23H,2-17H2,1H3,(H,25,26)/p-1
CAS number:Not Available
IUPAC Name:1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl tetradecanoate
Traditional IUPAC Name:1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl tetradecanoate
SMILES:CCCCCCCCCCCCCC(=O)OC(CO)COP([O-])(=O)OCC(O)CO
Chemical Taxonomy
Description 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).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentLysophosphatidylglycerols
Alternative Parents
Substituents
  • Monoacylglycerophosphoglycerol
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.059 g/LALOGPS
logP2.7ALOGPS
logP3.13ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area145.58 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity111.39 m³·mol⁻¹ChemAxon
Polarizability49.97 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Adenosine triphosphate + tetradecanoate (n-C14:0) > Adenosine monophosphate + PG(14:0/14:0) + Pyrophosphate
Water + PG(14:0/14:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Hydrogen ion + tetradecanoate (n-C14:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + Water > Glycerophosphoglycerol + Hydrogen ion + tetradecanoate (n-C14:0)
2-Acyl-sn-glycero-3-phosphoglycerol (N-C14:0) + PG(14:0/14:0) > Acyl phosphatidylglycerol (N-C14:0) + Glycerophosphoglycerol
SMPDB Pathways:Not Available
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-5350900000-7677f9b11d8b0569f4b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9650500000-947741087bb74303d64cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9210000000-8075c1fb883cabff42caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ufr-1160900000-c3d5ac46ed94e6b2fe9dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0un9-2951400000-a52f8713b8cd4fb7fcedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-9640000000-f9638473b682e4c55a40View 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:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID45479710
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2173
EcoCyc IDCPD0-2173

Enzymes

Protein Details
1. Lysophospholipase L2
General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Uniprot ID:
P07000
Molecular weight:
38978
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
Protein Details
2. Phospholipase A1
General function:
Involved in phospholipase activity
Specific function:
Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:
pldA
Uniprot ID:
P0A921
Molecular weight:
33163
Reactions
Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.
Protein Details
3. Bifunctional protein aas
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].

Transporters

Protein Details
1. Lysophospholipid transporter lplT
General function:
Involved in lipid transporter activity
Specific function:
Catalyzes the facilitated diffusion of 2-acyl-glycero-3- phosphoethanolamine (2-acyl-GPE) into the cell
Gene Name:
lplT
Uniprot ID:
P39196
Molecular weight:
41655