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Identification
YMDB IDYMDB13381
NameMG(16:0/0:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
Description1-monohexadecanoylglycerol, also known as (R)-1-monopalmitin or sn-glycerol 3-palmitate, belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position. 1-monohexadecanoylglycerol is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
Synonyms
  • (2R)-2,3-Dihydroxypropyl palmitate
  • (R)-1-Monopalmitin
  • (R)-2,3-Dihydroxypropyl N-hexadecanoate
  • 3-Hexadecanoyl-sn-glycerol
  • sn-Glycerol 3-palmitate
  • (2R)-2,3-Dihydroxypropyl palmitic acid
  • (R)-2,3-Dihydroxypropyl N-hexadecanoic acid
  • sn-Glycerol 3-palmitic acid
  • Palmitoyl glycerol
  • Palmitoyl glycerol, (+,-)-isomer
  • Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer
  • rac-1(3)-Palmitoyl glycerol
  • 1-Monohexadecanoyl-rac-glycerol
  • 1-Monopalmitin
  • 1-Glyceryl hexadecanoate
  • 1-Monohexadecanoylglycerol
CAS numberNot Available
WeightAverage: 330.5026
Monoisotopic: 330.277009704
InChI KeyQHZLMUACJMDIAE-GOSISDBHSA-N
InChIInChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3/t18-/m1/s1
IUPAC Name(2R)-2,3-dihydroxypropyl hexadecanoate
Traditional IUPAC Name(2R)-2,3-dihydroxypropyl hexadecanoate
Chemical FormulaC19H38O4
SMILESCCCCCCCCCCCCCCCC(=O)OC[C@H](O)CO
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassMonoradylglycerols
Direct Parent1-monoacylglycerols
Alternative Parents
Substituents
  • 1-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • 1,2-diol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0047 g/LALOGPS
logP5.73ALOGPS
logP5.08ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity94.11 m³·mol⁻¹ChemAxon
Polarizability42.39 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Organoleptic PropertiesNot Available
SMPDB Pathways
Triacylglycerol metabolismPW002695 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(10:0/10:0/25:1(15Z))PW007682 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(10:0/10:0/26:1(5Z))PW007711 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(10:0/15:1(9Z)/15:1(9Z))PW007606 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(10:0/15:1(9Z)/20:1(13Z))PW007692 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
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, Positivesplash10-03di-9351000000-f2f6a9e7c360a0c0a5b4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-6149000000-46e003ac9032083459dcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9231000000-984ad8a5384b8670209dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056u-9420000000-2b1d5a640ca0c7b0f0d0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a70-2094000000-2727de3f777ddd17bb39JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-4090000000-3e968d1b6b44f5a6c1e4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9060000000-9cc1ac16deaed570ab82JSpectraViewer
References
References:
  • Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID64757
HMDB IDNot Available
Pubchem Compound IDNot Available
Kegg IDNot Available
ChemSpider IDNot Available
FOODB IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available