You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
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
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-CoACoenzyme A + 1-palmitoylglycerone 3-phosphate
1-palmitoylglycerone 3-phosphate + NADPH + hydronPA(16:0/0:0) + NADP
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
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

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.
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.
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.