1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) (ECMDB21125) (M2MDB001534)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2012-07-30 14:54:39 -0600
Update Date2015-06-03 17:20:41 -0600
Secondary Accession Numbers
  • ECMDB21125
Identification
Name:1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0)
Description1-acyl-sn-glycero-3-phosphoglycerol (n-c18:0) 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:
  • 1-acyl-sn-glycero-3-phosphoglycerol (n-C18:0)
Chemical Formula:C24H48O9P
Weight:Average: 511.6063
Monoisotopic: 511.303594646
InChI Key:HFJVKBVEKQHVTO-UHFFFAOYSA-M
InChI:InChI=1S/C24H49O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(28)31-19-23(27)21-33-34(29,30)32-20-22(26)18-25/h22-23,25-27H,2-21H2,1H3,(H,29,30)/p-1
CAS number:Not Available
IUPAC Name:3-[(2,3-dihydroxypropyl phosphonato)oxy]-2-hydroxypropyl octadecanoate
Traditional IUPAC Name:3-[(2,3-dihydroxypropyl phosphonato)oxy]-2-hydroxypropyl octadecanoate
SMILES:CCCCCCCCCCCCCCCCCC(=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
  • 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 Solubility0.002 g/LALOGPS
logP4.4ALOGPS
logP4.91ChemAxon
logS-5.4ALOGPS
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 Count26ChemAxon
Refractivity129.8 m³·mol⁻¹ChemAxon
Polarizability58.45 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PG(18:0/18:0) > 1-Acyl-sn-glycero-3-phosphoglycerol (N-C18:0) + Hydrogen ion + Octadecanoate (N-C18:0)
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, Positivesplash10-03fr-7251290000-540734e1b80df55d5c4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9252500000-31972ea5830057c6f083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9130000000-4b9906649f4627714355View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03e9-1090150000-9e3db6463e8de5cf88fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0390000000-4bc7ec9b3ec488511aa8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9470000000-5e266ec0a4e187e0944eView 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 ID45479627
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2140
EcoCyc IDCPD0-2140

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.