Record Information
Version2.0
Creation Date2012-07-30 14:54:43 -0600
Update Date2015-06-03 17:20:47 -0600
Secondary Accession Numbers
  • ECMDB21166
Identification
Name:2-tetradecanoyl-sn-glycerol 3-phosphate
Description2-tetradecanoyl-sn-glycerol 3-phosphate belongs to the class of Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • 2-Tetradecanoyl-sn-glycerol 3-phosphoric acid
Chemical Formula:C17H35O7P
Weight:Average: 382.4294
Monoisotopic: 382.212039986
InChI Key:AKURFOGPABVRGG-UHFFFAOYSA-N
InChI:InChI=1S/C17H35O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(19)24-16(14-18)15-23-25(20,21)22/h16,18H,2-15H2,1H3,(H2,20,21,22)
CAS number:Not Available
IUPAC Name:[3-hydroxy-2-(tetradecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name:3-hydroxy-2-(tetradecanoyloxy)propoxyphosphonic acid
SMILES:CCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent2-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 2-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.02 g/LALOGPS
logP3.09ALOGPS
logP4.07ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity95.78 m³·mol⁻¹ChemAxon
Polarizability42.59 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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, Positivesplash10-07d0-3988000000-7ade2b39191d16e0ef6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0cds-6951000000-96ceff7758da9024967aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ar0-9610000000-68782d6eb5ce5c0a2d76View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-8978000000-9bf7583deed4d467b145View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-f09bfa5b91038b134fedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-19ae6a284119934e41a5View in MoNA
References
References:
  • 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 IDNot Available

Enzymes

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.
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.

Transporters

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