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Record Information
Version2.0
Creation Date2012-05-31 14:46:29 -0600
Update Date2015-06-03 17:20:04 -0600
Secondary Accession Numbers
  • ECMDB20469
Identification
Name:Distearoyl phosphatidate
DescriptionDistearoyl phosphatidate is a member of the chemical class known as Fatty Acid Esters. These are carboxylic ester derivatives of a fatty acid. Phosphatidates are precursors for many phosphoglycerides found in animals, plants and microbes including L-1-phosphatidylserine, L-1-phosphatidyl-ethanolamine, and cardiolipin.
Structure
Thumb
Synonyms:
  • Distearoyl phosphatidate
  • Distearoyl phosphatidic acid
Chemical Formula:C39H75O8P
Weight:Average: 702.9818
Monoisotopic: 702.519955888
InChI Key:YFWHNAWEOZTIPI-DIPNUNPCSA-L
InChI:InChI=1S/C39H77O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h37H,3-36H2,1-2H3,(H2,42,43,44)/p-2/t37-/m1/s1
CAS number:Not Available
IUPAC Name:(2R)-1-(octadecanoyloxy)-3-(phosphonatooxy)propan-2-yl octadecanoate
Traditional IUPAC Name:(2R)-1-(octadecanoyloxy)-3-(phosphonatooxy)propan-2-yl octadecanoate
SMILES:[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP([O-])([O-])=O)OC(=O)CCCCCCCCCCCCCCCCC
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic anion
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
  • 1-acyl-2-octadecanoyl-sn-glycero-3-phosphate(2-) (CHEBI:82921 )
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility4.3e-05 g/LALOGPS
logP9.12ALOGPS
logP13.66ChemAxon
logS-7.2ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area125.02 ŲChemAxon
Rotatable Bond Count40ChemAxon
Refractivity194.73 m³·mol⁻¹ChemAxon
Polarizability87.41 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
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-0030001900-710625de9f2f9caad006View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fbl-3490005300-6958479818de104a8777View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-3492100000-84ecb1b1ffd6fc00da40View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ue9-0090000800-f53f56058009b29ccabcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000100-6bf65f2143a90e870f09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00m0-4190000000-d40bfbcc1081421aca17View in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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 ID82921
HMDB IDNot Available
Pubchem Compound ID25200924
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDCPD0-1423
EcoCyc IDCPD0-1423

Enzymes

General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsC
Uniprot ID:
P26647
Molecular weight:
27453
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1,2-diacyl-sn-glycerol 3-phosphate.