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1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) (M2MDB001532)

Record Information
Version2.0
Creation Date2012-07-30 14:54:39 -0600
Update Date2015-06-03 17:20:41 -0600
Secondary Accession Numbers
  • ECMDB21123
Identification
Name:1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0)
Description1-acyl-sn-glycero-3-phosphoglycerol (n-c16:0) 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). (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2,3-dihydroxypropyl (3-hexadecanoyloxy-2-hydroxypropyl) phosphate
  • 2,3-Dihydroxypropyl (3-hexadecanoyloxy-2-hydroxypropyl) phosphoric acid
Chemical Formula:C22H44O9P
Weight:Average: 483.5531
Monoisotopic: 483.272294518
InChI Key:BVJSKAUUFXBDOB-UHFFFAOYSA-M
InChI:InChI=1S/C22H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(26)29-17-21(25)19-31-32(27,28)30-18-20(24)16-23/h20-21,23-25H,2-19H2,1H3,(H,27,28)/p-1
CAS number:Not Available
IUPAC Name:3-[(2,3-dihydroxypropyl phosphonato)oxy]-2-hydroxypropyl hexadecanoate
Traditional IUPAC Name:lysophosphatidylglycerol
SMILES:CCCCCCCCCCCCCCCC(=O)OCC(O)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
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • 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 Solubility0.0033 g/LALOGPS
logP3.57ALOGPS
logP4.02ChemAxon
logS-5.2ALOGPS
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 Count24ChemAxon
Refractivity120.6 m³·mol⁻¹ChemAxon
Polarizability54.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
Water + PG(16:0/16:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Hydrogen ion + Palmitic acid
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, Positivesplash10-001i-5330900000-85fdaf89c108fc06d5caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0adi-9650600000-0cebcb97005eac5f353bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9310000000-632b450efa626c84711eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-0090600000-354bf074a7f3757c1a69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0390000000-7555699cf4b9c28dd140View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9370000000-c9b0305b76c6890fda63View in MoNA
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 ID3300275
Kegg IDNot Available
ChemSpider ID2548638
Wikipedia IDNot Available
BioCyc IDCPD0-2162
EcoCyc IDCPD0-2162

Enzymes

Protein Details
1. 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
2. Acyl-CoA thioesterase I
General function:
Involved in hydrolase activity
Specific function:
Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:
tesA
Uniprot ID:
P0ADA1
Molecular weight:
23622
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.