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1-palmitoylglycerone 3-phosphate (YMDB00187)

Identification
YMDB IDYMDB00187
Name1-palmitoylglycerone 3-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description1-palmitoyl-dihydroxyacetone-phosphate, also known as palmitoyl glycerone phosphoric acid or hexadecanoyl dihydroxyacetone phosphoric acid, belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position. 1-palmitoyl-dihydroxyacetone-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 1-palmitoylglycerone 3-phosphate
  • Hexadecanoic acid 2-oxo-3-(phosphonooxy)propyl ester
  • Hexadecanoyl dihydroxyacetone phosphate
  • Palmitoyl dihydroxyacetone phosphate
  • Palmitoyl glycerone phosphate
  • Palmitoylglycerone phosphate
  • Hexadecanoate 2-oxo-3-(phosphonooxy)propyl ester
  • Hexadecanoyl dihydroxyacetone phosphoric acid
  • Palmitoyl dihydroxyacetone phosphoric acid
  • Palmitoyl glycerone phosphoric acid
  • Palmitoylglycerone phosphoric acid
  • 1-Palmitoyl-dihydroxyacetone-phosphoric acid
  • 1-Palmitoylglycerone 3-phosphoric acid
CAS numberNot Available
WeightAverage: 408.4666
Monoisotopic: 408.22769005
InChI KeyMLWXSIMRTQAWHY-UHFFFAOYSA-N
InChIInChI=1S/C19H37O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h2-17H2,1H3,(H2,22,23,24)
IUPAC Name[3-(hexadecanoyloxy)-2-oxopropoxy]phosphonic acid
Traditional IUPAC Namepalmitoylglycerone phosphate
Chemical FormulaC19H37O7P
SMILESCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentO-acylglycerone-phosphates
Alternative Parents
Substituents
  • O-acylglycerone-phosphate
  • Monosaccharide phosphate
  • Fatty acid ester
  • Alpha-acyloxy ketone
  • Monoalkyl phosphate
  • Monosaccharide
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Fatty acyl
  • Alkyl phosphate
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0014 g/LALOGPS
logP4.57ALOGPS
logP5.27ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area110.13 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity104.06 m³·mol⁻¹ChemAxon
Polarizability46.33 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Endoplasmic Reticulum, Lipid Particle
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
Glycerone phosphate + Palmityl-CoA ↔ Coenzyme A + 1-palmitoylglycerone 3-phosphate
1-palmitoylglycerone 3-phosphate + NADPH + hydron → PA(16:0/0:0) + NADP
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-3931000000-b1d81e76708bda171f0eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4j-5367900000-5dbbb700186815389426JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pa-4984100000-9101a6686b51c7757e68JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9520000000-b7d302f5f61ac047a04bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-7391800000-4a3e8e2385e0a6ee1f3bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-478f0cf685c7a6415693JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8712ebcd8abea65d5ddaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1000900000-6f4b2cc601bf507b914aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a6r-6190000000-0e156bb88375e6f4d190JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-8980000000-ed97479c027e89c7278cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r6-0019200000-2c80c393c43f71d4a3b1JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-0293000000-193d220aa9da9d16b804JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052e-9100000000-6596ffb2fe0de423dfc1JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17868
HMDB IDHMDB0062190
Pubchem Compound ID167650
Kegg IDC01192
ChemSpider ID146664
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Glycerol-3-phosphate O-acyltransferase 1
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT1
Uniprot ID:
P32784
Molecular weight:
85693.5
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
2. Glycerol-3-phosphate O-acyltransferase 2
General function:
Involved in acyltransferase activity
Specific function:
G-3-P/dihydroxyacetone phosphate dual substrate-specific sn-1 acyltransferase
Gene Name:
GPT2
Uniprot ID:
P36148
Molecular weight:
83644.0
Reactions
Acyl-CoA + sn-glycerol 3-phosphate → CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-CoA + glycerone phosphate → CoA + acylglycerone phosphate.
Protein Details
3. NADPH-dependent 1-acyldihydroxyacetone phosphate reductase
General function:
Involved in oxidoreductase activity
Specific function:
Can convert acyl and alkyl dihydroxyacetone-phosphate (DHAP) into glycerolipids and ether lipids, respectively. Required for the biosynthesis of phosphatidic acid via the DHAP pathway, where it reduces 1-acyl DHAP to lysophosphatidic acid (LPA). Required for spore germination
Gene Name:
AYR1
Uniprot ID:
P40471
Molecular weight:
32813.60156
Reactions
1-palmitoylglycerol 3-phosphate + NADP(+) → palmitoylglycerone phosphate + NADPH.