Record Information
Version 1.0
Update Date 1/22/2018 11:54:53 AM
Metabolite IDPAMDB001558
Identification
Name: 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0)
Description:2-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).
Structure
Thumb
Synonyms:
  • 2-16:0-Lysophosphatidylglycerol
  • 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0)
  • 2-Hexadecanoyl-sn-glycero-3-phospho-(1'-sn-glycerol)
Chemical Formula: C22H44O9P
Average Molecular Weight: 483.5531
Monoisotopic Molecular Weight: 483.272294518
InChI Key: ODJYINYQGFIIRK-UHFFFAOYSA-M
InChI:InChI=1S/C22H45O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-22(26)31-21(17-24)19-30-32(27,28)29-18-20(25)16-23/h20-21,23-25H,2-19H2,1H3,(H,27,28)/p-1
CAS number: Not Available
IUPAC Name:1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl hexadecanoate
Traditional IUPAC Name: 1-[(2,3-dihydroxypropyl phosphonato)oxy]-3-hydroxypropan-2-yl hexadecanoate
SMILES:CCCCCCCCCCCCCCCC(=O)OC(CO)COP([O-])(=O)OCC(O)CO
Chemical Taxonomy
Taxonomy DescriptionThis compound 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).
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct Parent Lysophosphatidylglycerols
Alternative Parents
Substituents
  • Monoacylglycerophosphoglycerol
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Saccharide
  • Secondary alcohol
  • Carboxylic acid ester
  • 1,2-diol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.00326 mg/mLALOGPS
logP3.56ALOGPS
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 Å2ChemAxon
Rotatable Bond Count24ChemAxon
Refractivity120.6 m3·mol-1ChemAxon
Polarizability53.91 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, Positivesplash10-001i-6340900000-7faff06545f20bbd2197View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-9560600000-a60c34ea27aed5485692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-9210000000-264e0192064efb9983b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053r-1160900000-111484349cae994a377fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0759-2980600000-93cb622013ea0f6a17a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9550000000-b6d84006e5b7d38430c9View 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 ID25201911
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD-8363
EcoCyc IDCPD-8363

Enzymes

General function:
Lipid transport and metabolism
Specific function:
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:
pldB
Locus Tag:
PA5089
Molecular weight:
83.4 kDa
Reactions
2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.
General function:
Involved in N-acyltransferase activity
Specific function:
Transfers the fatty acyl group on membrane lipoproteins
Gene Name:
lnt
Locus Tag:
PA3984
Molecular weight:
56 kDa

Transporters