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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-02-24 01:29:35 UTC
Update Date2019-07-23 07:17:57 UTC
HMDB IDHMDB0062190
Secondary Accession Numbers
  • HMDB62190
Metabolite Identification
Common Name1-palmitoyl-dihydroxyacetone-phosphate
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
Data?1563866277
Synonyms
ValueSource
Hexadecanoic acid 2-oxo-3-(phosphonooxy)propyl esterChEBI
Hexadecanoyl dihydroxyacetone phosphateChEBI
Palmitoyl dihydroxyacetone phosphateChEBI
Palmitoyl glycerone phosphateChEBI
Palmitoylglycerone phosphateChEBI
Hexadecanoate 2-oxo-3-(phosphonooxy)propyl esterGenerator
Hexadecanoyl dihydroxyacetone phosphoric acidGenerator
Palmitoyl dihydroxyacetone phosphoric acidGenerator
Palmitoyl glycerone phosphoric acidGenerator
Palmitoylglycerone phosphoric acidGenerator
1-Palmitoyl-dihydroxyacetone-phosphoric acidGenerator
1-Palmitoylglycerone 3-phosphoric acidGenerator
Chemical FormulaC19H37O7P
Average Molecular Weight408.4666
Monoisotopic Molecular Weight408.22769005
IUPAC Name[3-(hexadecanoyloxy)-2-oxopropoxy]phosphonic acid
Traditional Namepalmitoylglycerone phosphate
CAS Registry Number17378-38-0
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O
InChI Identifier
InChI=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)
InChI KeyMLWXSIMRTQAWHY-UHFFFAOYSA-N
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0014 g/lALOGPS
LogP4.57ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(4.57) g/LALOGPS
logP10(5.27) g/LChemAxon
logS10(-5.5) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+191.23630932474
DeepCCS[M-H]-188.5130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-palmitoyl-dihydroxyacetone-phosphateCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O3550.3Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphateCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O2677.3Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphateCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O3062.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C3012.0Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C2859.0Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C3930.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C3040.1Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C2852.5Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C4351.9Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C3095.9Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C2853.9Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C4506.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3047.4Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2918.2Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3386.2Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3112.2Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2892.3Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3713.6Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3119.4Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2894.0Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3767.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3130.7Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2901.1Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3221.6Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3148.5Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2914.2Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3272.6Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3269.3Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3035.4Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3995.8Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3309.1Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2986.8Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O)O[Si](C)(C)C(C)(C)C4323.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3344.1Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C2993.2Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,1TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C4452.9Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3560.9Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3193.8Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3533.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3572.1Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3157.3Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3813.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3595.9Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3169.2Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,2TBDMS,isomer #3CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3826.0Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3784.9Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3263.3Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCC(=O)OCC(=COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3451.5Standard polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3822.3Semi standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3290.1Standard non polar33892256
1-palmitoyl-dihydroxyacetone-phosphate,3TBDMS,isomer #2CCCCCCCCCCCCCCCC(=O)OC=C(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3470.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01p9-3931000000-b1d81e76708bda171f0e2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 10V, Positive-QTOFsplash10-0a4j-5367900000-5dbbb7001868153894262016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 20V, Positive-QTOFsplash10-01pa-4984100000-9101a6686b51c7757e682016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 40V, Positive-QTOFsplash10-000w-9520000000-b7d302f5f61ac047a04b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 10V, Negative-QTOFsplash10-0a70-7391800000-4a3e8e2385e0a6ee1f3b2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 20V, Negative-QTOFsplash10-004i-9010000000-478f0cf685c7a64156932016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-8712ebcd8abea65d5dda2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 10V, Negative-QTOFsplash10-0a4i-1000900000-6f4b2cc601bf507b914a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 20V, Negative-QTOFsplash10-0a6r-6190000000-0e156bb88375e6f4d1902021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 40V, Negative-QTOFsplash10-0ab9-8980000000-ed97479c027e89c7278c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 10V, Positive-QTOFsplash10-06r6-0019200000-2c80c393c43f71d4a3b12021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 20V, Positive-QTOFsplash10-01p9-0293000000-193d220aa9da9d16b8042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-palmitoyl-dihydroxyacetone-phosphate 40V, Positive-QTOFsplash10-052e-9100000000-6596ffb2fe0de423dfc12021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID146664
KEGG Compound IDC01192
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound167650
PDB IDNot Available
ChEBI ID17868
Food Biomarker OntologyNot Available
VMH IDM00550
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available