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2-hexadecanoyl-sn-glycerol 3-phosphate (M2MDB001570)

Record Information
Version2.0
Creation Date2012-07-30 14:54:43 -0600
Update Date2015-06-03 17:20:46 -0600
Secondary Accession Numbers
  • ECMDB21161
Identification
Name:2-hexadecanoyl-sn-glycerol 3-phosphate
Description2-hexadecanoyl-sn-glycerol 3-phosphate belongs to the class of Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. (inferred from compound structure)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-Hexadecanoyl-sn-glycerol 3-phosphoric acid
Chemical Formula:C19H39O7P
Weight:Average: 410.4825
Monoisotopic: 410.243340114
InChI Key:LPQBQFLKBCPNAV-UHFFFAOYSA-N
InChI:InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)26-18(16-20)17-25-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)
CAS number:Not Available
IUPAC Name:[2-(hexadecanoyloxy)-3-hydroxypropoxy]phosphonic acid
Traditional IUPAC Name:2-(hexadecanoyloxy)-3-hydroxypropoxyphosphonic acid
SMILES:CCCCCCCCCCCCCCCC(=O)OC(CO)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent2-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 2-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0027 g/LALOGPS
logP3.96ALOGPS
logP4.96ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.98 m³·mol⁻¹ChemAxon
Polarizability46.84 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
Water + PA(16:0/16:0) > 2-hexadecanoyl-sn-glycerol 3-phosphate + Palmitic acid
2-hexadecanoyl-sn-glycerol 3-phosphate + Water > Glycerol 3-phosphate +2 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 GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01ot-9440000000-bf1d1f237edf728eb2c5View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08g0-3975600000-8a269b545c4d24da9aadView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btj-6952000000-be4d81f8aa90afc59905View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054k-9720000000-2af12860245e1cdaf48fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9871700000-49682f37e6e51ea574e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9110000000-ad3918383a58c2aba398View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4a8a491ed626534005d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-2039500000-ff5001fecfa0d240ff69View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-2695000000-cc51ff937b2c609be46fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9100000000-832946b2e9b8f954e29cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-4000900000-0d0d9baf6df77f542e34View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-9100000000-0954a22e4e318311db16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a195e098f58b4f2bb72eView 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 IDNot Available
HMDB IDHMDB0007849
Pubchem Compound ID56960317
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

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.

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