Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001538
Identification
Name: 1-hexadecanoyl-sn-glycerol 3-phosphate
Description:1-hexadecanoyl-sn-glycerol 3-phosphate belongs to the class of Lysophosphatidic Acids. These are glycerophosphates where the glycerol is esterified with one saturated fatty acid. (inferred from compound structure)
Structure
Thumb
Synonyms:
  • (2-hydroxy-3-phosphonooxypropyl) hexadecanoate
  • (2-Hydroxy-3-phosphonooxypropyl) hexadecanoic acid
  • 1-Hexadecanoyl-sn-glycero-3-phosphate
  • 1-Hexadecanoyl-sn-glycero-3-phosphoric acid
  • 1-Hexadecanoyl-sn-glycerol 3-phosphoric acid
  • 1-Palmitoyl lysophosphatidate
  • 1-Palmitoyl lysophosphatidic acid
  • 1-Palmitoylglycerol 3-phosphate
  • 1-Palmitoylglycerol 3-phosphoric acid
Chemical Formula: C19H39O7P
Average Molecular Weight: 410.4825
Monoisotopic Molecular Weight: 410.243340114
InChI Key: YNDYKPRNFWPPFU-UHFFFAOYSA-N
InChI:InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)
CAS number: Not Available
IUPAC Name:[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name: PLPA
SMILES:CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphates
Direct Parent 1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Organic phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
  • Monoacylglycerophosphates (C04036 )
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00242 mg/mLALOGPS
logP3.87ALOGPS
logP4.96ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.98 m3·mol-1ChemAxon
Polarizability47.18 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-2986700000-f3b30f5c39843042fd11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-3942000000-0e96d3c410d5f67cbc44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-6930000000-8e619c799b8a218b3a05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-4190300000-bb83e3f01055cbe6102fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-de299cedb3cf89da4492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f3fc94f808e80bf00353View 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 ID64023
HMDB IDNot Available
Pubchem Compound ID89566
Kegg IDC04036
ChemSpider ID80836
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsB
Locus Tag:
PA3673
Molecular weight:
94.8 kDa
Reactions
Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Locus Tag:
PA2856
Molecular weight:
21 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in fatty acid biosynthetic process
Specific function:
Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:
acpP
Locus Tag:
PA2966
Molecular weight:
8.7 kDa