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Acyl phosphatidylglycerol (N-C18:1) (M2MDB001710)

Record Information
Version2.0
Creation Date2012-07-30 14:55:16 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB21306
Identification
Name:Acyl phosphatidylglycerol (N-C18:1)
DescriptionPhosphatidylglycerol is a glycerophospholipid. The general structure of phosphatidylglycerol consists of a L-glycerol 3-phosphate backbone ester-bonded to either saturated or unsaturated fatty acids on carbons 1 and 2. The head group substituent glycerol is bonded through a phosphomonoester. Phosphatidylglycerol is important as an intermediate for biosynthesis of other lipids, including cardiolipins.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
3-({2,3-bis[(11E)-octadec-11-enoyloxy]propyl phosphonato}oxy)-2-hydroxypropyl (11E)-octadec-11-enoic acidGenerator
Chemical Formula:C60H110O11P
Weight:Average: 1038.4826
Monoisotopic: 1037.778575874
InChI Key:MNEWMEXDRDMOEP-IKVQWSBMSA-M
InChI:InChI=1S/C60H111O11P/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-58(62)67-52-56(61)53-69-72(65,66)70-55-57(71-60(64)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)54-68-59(63)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h19-24,56-57,61H,4-18,25-55H2,1-3H3,(H,65,66)/p-1/b22-19+,23-20+,24-21+
CAS number:Not Available
IUPAC Name:3-({2,3-bis[(11E)-octadec-11-enoyloxy]propyl phosphonato}oxy)-2-hydroxypropyl (11E)-octadec-11-enoate
Traditional IUPAC Name:3-({2,3-bis[(11E)-octadec-11-enoyloxy]propyl phosphonato}oxy)-2-hydroxypropyl (11E)-octadec-11-enoate
SMILES:[H]\C(CCCCCC)=C(\[H])CCCCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC(COC(=O)CCCCCCCCC\C([H])=C(/[H])CCCCCC)OC(=O)CCCCCCCCC\C([H])=C(/[H])CCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as semilysobisphosphatidic acids. These are bisphosphatidic acid analogues with three moles of fatty acid per mole of lipid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassSemilysobisphosphatidic acids
Direct ParentSemilysobisphosphatidic acids
Alternative Parents
Substituents
  • Semilysobisphosphatidic acid
  • Tricarboxylic acid or derivatives
  • Dialkyl phosphate
  • Fatty acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.3e-05 g/LALOGPS
logP9.63ALOGPS
logP19.44ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area157.72 ŲChemAxon
Rotatable Bond Count59ChemAxon
Refractivity298.73 m³·mol⁻¹ChemAxon
Polarizability130.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
2-Acyl-sn-glycero-3-phosphoethanolamine (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoglycerol (N-C18:1) + PG(18:1(11Z)/18:1(11Z)) > Acyl phosphatidylglycerol (N-C18:1) + 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, Positivesplash10-000i-9000000000-af7cb0165e57a2e3cd86View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9011000000-e7e202f5bd8009ec1c37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6u-9031011300-d17fda5c9159c8052ca6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-9000000000-97f701ba5a225354afedView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-9050000300-bf31eda2cbd298754fa7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-9080000100-98de9ce411cb1b450cc8View 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 IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-2179
EcoCyc IDCPD0-2179

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.