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2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) (M2MDB001558)

Record Information
Version2.0
Creation Date2012-07-30 14:54:41 -0600
Update Date2015-06-03 17:20:45 -0600
Secondary Accession Numbers
  • ECMDB21149
Identification
Name:2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0)
Description2-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
MOLSDFPDBSMILESInChI
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
Weight:Average: 483.5531
Monoisotopic: 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
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
logP3.56ALOGPS
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 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity120.6 m³·mol⁻¹ChemAxon
Polarizability53.91 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
applipoprotein + PG(16:0/16:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + lipoprotein
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Adenosine triphosphate + Palmitic acid > Adenosine monophosphate + PG(16:0/16:0) + Pyrophosphate
Water + PG(16:0/16:0) > 2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + Water > Glycerophosphoglycerol + Hydrogen ion + Palmitic acid
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:0) + PG(16:0/16:0) > Acyl phosphatidylglycerol (N-C16:0) + Glycerophosphoglycerol
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-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

Protein Details
1. Lysophospholipase L2
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.
Protein Details
2. 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
3. Bifunctional protein aas
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Plays a role in lysophospholipid acylation. Transfers fatty acids to the 1-position via an enzyme-bound acyl-ACP intermediate in the presence of ATP and magnesium. Its physiological function is to regenerate phosphatidylethanolamine from 2-acyl-glycero-3-phosphoethanolamine (2-acyl-GPE) formed by transacylation reactions or degradation by phospholipase A1
Gene Name:
aas
Uniprot ID:
P31119
Molecular weight:
80699
Reactions
Acyl-[acyl-carrier-protein] + O-(2-acyl-sn-glycero-3-phospho)ethanolamine = [acyl-carrier-protein] + O-(1-beta-acyl-2-acyl-sn-glycero-3-phospho)ethanolamine.
ATP + an acid + [acyl-carrier-protein] = AMP + diphosphate + acyl-[acyl-carrier-protein].
Protein Details
4. Major outer membrane lipoprotein Lpp
General function:
Involved in lipid binding
Specific function:
Interacts with the peptidoglycan both covalently and noncovalently. This interaction contributes to the maintenance of the structural and functional integrity of the cell envelope
Gene Name:
lpp
Uniprot ID:
P69776
Molecular weight:
8323
Protein Details
5. Apolipoprotein N-acyltransferase
General function:
Involved in N-acyltransferase activity
Specific function:
Transfers the fatty acyl group on membrane lipoproteins
Gene Name:
lnt
Uniprot ID:
P23930
Molecular weight:
57065

Transporters

Protein Details
1. Lysophospholipid transporter lplT
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