Acyl phosphatidylglycerol (N-C16:1) (ECMDB21304) (M2MDB001708)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (1)XML
Proteins (1)
Record Information
Version2.0
Creation Date2012-07-30 14:55:16 -0600
Update Date2015-09-16 14:50:11 -0600
Secondary Accession Numbers
  • ECMDB21304
Identification
Name:Acyl phosphatidylglycerol (N-C16:1)
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. Glycerophospholipids are important intermediates in cardiolipin synthesis.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
1-[(9E)-Hexadec-9-enoyloxy]-3-({3-[(9E)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphonato}oxy)propan-2-yl (9E)-hexadec-9-enoic acidGenerator
Chemical Formula:C54H98O11P
Weight:Average: 954.3231
Monoisotopic: 953.68467549
InChI Key:ISOXHMBLKVGIAT-IKVQWSBMSA-M
InChI:InChI=1S/C54H99O11P/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-52(56)61-46-50(55)47-63-66(59,60)64-49-51(65-54(58)45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)48-62-53(57)44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h19-24,50-51,55H,4-18,25-49H2,1-3H3,(H,59,60)/p-1/b22-19+,23-20+,24-21+
CAS number:Not Available
IUPAC Name:1-[(9E)-hexadec-9-enoyloxy]-3-({3-[(9E)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphonato}oxy)propan-2-yl (9E)-hexadec-9-enoate
Traditional IUPAC Name:1-[(9E)-hexadec-9-enoyloxy]-3-({3-[(9E)-hexadec-9-enoyloxy]-2-hydroxypropyl phosphonato}oxy)propan-2-yl (9E)-hexadec-9-enoate
SMILES:[H]\C(CCCCCC)=C(\[H])CCCCCCCC(=O)OCC(O)COP([O-])(=O)OCC(COC(=O)CCCCCCC\C([H])=C(/[H])CCCCCC)OC(=O)CCCCCCC\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 Solubility3.4e-05 g/LALOGPS
logP9.3ALOGPS
logP16.77ChemAxon
logS-7.5ALOGPS
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 Count53ChemAxon
Refractivity271.13 m³·mol⁻¹ChemAxon
Polarizability117.93 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-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + Glycerylphosphorylethanolamine
2-Acyl-sn-glycero-3-phosphoglycerol (N-C16:1) + PG(16:1(9Z)/16:1(9Z)) > Acyl phosphatidylglycerol (N-C16:1) + 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, Positivesplash10-0udi-0000000009-8fbba484eef1a7c437c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-1010000009-55263f04864f968fa887View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4m-9440021202-835fd692ae035a539057View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000000009-2fb2f2243802f371d789View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0050001209-dd2da2fdf2f7b624230fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ue9-9070001000-c5c17634baa5730873efView 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 IDCPD0-2198
EcoCyc IDCPD0-2198

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.