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Record Information
Version4.0
Creation Date2012-09-11 17:40:49 UTC
Update Date2017-10-23 19:07:11 UTC
HMDB IDHMDB0031075
Secondary Accession Numbers
  • HMDB31075
Metabolite Identification
Common NameGlycerol 1-octadecanoate
DescriptionGlyceryl monostearate is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]")
Structure
Thumb
Synonyms
ValueSource
1-OctadecanoylglycerolChEBI
1-Stearoyl-glycerolChEBI
Glyceryl monostearateChEBI
MAG(18:0)ChEBI
MAG(18:0/0:0)ChEBI
MG(18:0)ChEBI
MG(18:0/0:0)ChEBI
Glycerol 1-octadecanoic acidGenerator
Glyceryl monostearic acidGenerator
(1)-2,3-Dihydroxypropyl stearateHMDB
1,2,3-Propanetriol 1-octadecanoyl esterHMDB
1,2,3-Propanetriol monooctadecanoateHMDB
1,2,3-Propanetriol, homopolymer, isooctadecanoateHMDB
1-Glyceryl stearateHMDB
1-mono-StearinHMDB
1-Monooctadecanoyl-rac-glycerolHMDB
1-MonostearinHMDB
1-MonostearoylglycerolHMDB
1-O-OctadecanoylglycerolHMDB
1-O-StearoylglycerolHMDB
1-Stearoyl-rac-glycerolHMDB
2,3-Dihydroxypropyl stearateHMDB
3-Stearoyloxy-1,2-propanediolHMDB
a-MonostearinHMDB
alpha-MonostearinHMDB
CefatinHMDB
DermagineHMDB
e471?HMDB
FEMA 2527HMDB
Glycerin 1-monostearateHMDB
Glycerin 1-stearateHMDB
Glycerol 1-monostearateHMDB
Glycerol 1-stearateHMDB
Glycerol alpha -monostearateHMDB
Glycerol alpha -sterateHMDB
Glycerol alpha-monostearateHMDB
Glyceryl 1-monostearateHMDB
Glyceryl-1-monostearateHMDB
Octadecanoic acid 2,3-dihydroxypropyl esterHMDB
Octadecanoic acid, 2,3-dihydroxypropyl esterHMDB
Octadecanoic acid, ester with 1,2,3-propanetriolHMDB
Stearic acid 1-monoglycerideHMDB
Stearic acid alpha -monoglycerideHMDB
Stearic acid alpha-monoglycerideHMDB
Chemical FormulaC21H42O4
Average Molecular Weight358.5558
Monoisotopic Molecular Weight358.308309832
IUPAC Name2,3-dihydroxypropyl octadecanoate
Traditional Nameglyceryl stearate
CAS Registry Number123-94-4
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO
InChI Identifier
InChI=1S/C21H42O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(24)25-19-20(23)18-22/h20,22-23H,2-19H2,1H3
InChI KeyVBICKXHEKHSIBG-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassGlycerolipids
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
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point77 - 79 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP6.73ALOGPS
logP5.97ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity103.31 m³·mol⁻¹ChemAxon
Polarizability46.63 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-007k-9530000000-e7c8759540fb484bf4afView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f6t-2910000000-94597a6f353acb356316View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-000i-9670300000-c997fc24da788ae94c35View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-2580e940ca1f2f1cbca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-2580e940ca1f2f1cbca3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0be6-0069000000-6f7c44088fdbecb9e384View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Feces
  • Sweat
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SweatDetected but not Quantified Adult BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB009515
KNApSAcK IDNot Available
Chemspider ID23095
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24699
PDB IDNot Available
ChEBI ID526874
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  6. (). EAFUS: Everything Added to Food in the United States.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.