Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB001708
Identification
Name: Acyl phosphatidylglycerol (N-C16:1)
Description:Phosphatidylglycerol 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
Synonyms:Not Available
Chemical Formula: C54H98O11P
Average Molecular Weight: 954.3231
Monoisotopic Molecular Weight: 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
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassSemilysobisphosphatidic acids
Direct Parent Semilysobisphosphatidic 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
  • Organic phosphate
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors Not Available
Physical Properties
State: Not Available
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility3.43e-05 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count53ChemAxon
Refractivity271.13 m3·mol-1ChemAxon
Polarizability117.93 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
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, Positivesplash10-0udi-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