Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2017-08-01 02:17:14 UTC
Update Date2019-02-12 06:09:52 UTC
HMDB IDHMDB0094684
Secondary Accession Numbers
  • HMDB94684
Metabolite Identification
Common NameMonooleoylglycerol
DescriptionMonooleoylglycerol, also known as glyceryl 1-oleate, glycerylmonooleate or 1-monoolein, is classified as a member of the 1-monoacylglycerols. 1-Monoacylglycerols are monoacylglycerols containing a glycerol acylated at the 1-position. Monooleoylglycerol is considered to be practically insoluble (in water) and relatively neutral.  Monooleoylglycerol is a monoradylglycerol lipid molecule. (ChemoSummarizer)
Structure
Data?1549951792
Synonyms
ValueSource
1-(9Z)-OctadecenoylglycerolChEBI
1-(9Z-Octadecenoyl)-rac-glycerolChEBI
1-MonooleinChEBI
1-Monooleoyl-rac-glycerolChEBI
1-MonooleoylglycerolChEBI
1-Oleoyl-rac-glycerolChEBI
2,3-Dihydroxypropyl oleateChEBI
MG (18:1/0:0/0:0)ChEBI
2,3-Dihydroxypropyl oleic acidGenerator
1-Oleoyl monoglycerideMeSH
1-Oleoyl-2-glycerolMeSH
MonoelaidinMeSH
Myverol 18-99MeSH
sn-1-O-(cis-9)OctadecenylglycerolMeSH
Glyceryl monooleateMeSH
MonoleinMeSH
Glycerol monooleateMeSH
GlycerylmonooleateMeSH
mono-OleoylglycerolMeSH
Oleic acid monoglycerideMeSH
Chemical FormulaC21H40O4
Average Molecular Weight356.5399
Monoisotopic Molecular Weight356.292659768
IUPAC Name2,3-dihydroxypropyl (9Z)-octadec-9-enoate
Traditional Nameoleoyl glycerol
CAS Registry NumberNot Available
SMILES
[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)OCC(O)CO
InChI Identifier
InChI=1S/C21H40O4/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/h9-10,20,22-23H,2-8,11-19H2,1H3/b10-9-
InChI KeyRZRNAYUHWVFMIP-KTKRTIGZSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.32ALOGPS
logP5.61ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)13.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count19ChemAxon
Refractivity104.43 m³·mol⁻¹ChemAxon
Polarizability44.79 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ufr-3941000000-863ed9a1a307beb4a1a8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ot-8950000000-35c590cce9dff8869298JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ufs-1900000000-ecd5f6a96f0e3005d450JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0f79-9561400000-65fdf1d5087668734b1eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0532-0069000000-8ebd454263638be9a356JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-06rt-0069000000-0ca2c02d94f2434099c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-001i-0094000000-ae9df2b39a5a3e609d9eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-052b-0069000000-1b2499b87288e3a0cc7cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-052b-0069000000-61627df65991c534b2fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0gb9-0013649000-09e4a7f8726d9fa56e6dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0013549000-913cbee00d9ce0f8129dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0002-0059000000-a485dc334652f9d25ebfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-054k-0049000000-3cce669ed7aca2869e31JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0009000000-6278c7e8ab10862172daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0009000000-6278c7e8ab10862172daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0boi-0069000000-468bbe23a7c3125ab01cJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Weir TL, Manter DK, Sheflin AM, Barnett BA, Heuberger AL, Ryan EP: Stool microbiome and metabolome differences between colorectal cancer patients and healthy adults. PLoS One. 2013 Aug 6;8(8):e70803. doi: 10.1371/journal.pone.0070803. Print 2013. [PubMed:23940645 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-11690
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283468
PDB IDNot Available
ChEBI ID75342
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.