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Record Information
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-09-27 08:28:01 UTC
Secondary Accession Numbers
  • HMDB15638
Metabolite Identification
Common NameEthanolamine Oleate
DescriptionEthanolamine Oleate is only found in individuals that have used or taken this drug. It is a mild sclerosing agent. It is composed of ethanolamine, a basic substance, which when combined with oleic acid forms a clear, straw to pale yellow colored, deliquescent oleate.The oleic acid component of ethanolamine oleate is responsible for the inflammatory response, and may also activate coagulation in vivo by release of tissue factor and activation of Hageman factor. The ethanolamine component, however, may inhibit fibrin clot formation by chelating calcium, so that a procoagulant action of ethanolamine oleate has not been demonstrated.
Monoethanolamine oleateKegg
Monoethanolamine oleic acidGenerator
Ethanolamine oleic acidGenerator
beta-Hydroxyethylammonium oleateHMDB
cis-9-Octadecenoic acid, ethanolamine saltHMDB
Chemical FormulaC20H41NO3
Average Molecular Weight343.5444
Monoisotopic Molecular Weight343.308644183
IUPAC Name(9Z)-octadec-9-enoic acid; 2-aminoethan-1-ol
Traditional Nameethanolamine; oleic acid
CAS Registry Number2272-11-9
InChI Identifier
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
Direct ParentLong-chain fatty acids
Alternative Parents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkNot Available
External DescriptorsNot Available

Biological Location:


  Biofluid and excreta:


Route of exposure:



Industrial application:

  Pharmaceutical industry:

Biological role:


Naturally occurring process:

  Biological process:

    Cellular process:

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Physical Properties
Experimental Properties
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity87.4 m³·mol⁻¹ChemAxon
Polarizability37.09 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ( TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0009000000-7a39d2ea52a4892093c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0009000000-7a39d2ea52a4892093c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0009000000-7a39d2ea52a4892093c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-7549513ded94c90c45adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0009000000-7549513ded94c90c45adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0009000000-7549513ded94c90c45adView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
No entries found
Normal Concentrations
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06689 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB06689 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06689
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4445632
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMonoethanolamine_oleate
METLIN IDNot Available
PubChem Compound5282489
PDB IDNot Available
ChEBI IDNot Available
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kang JH, Kambayashi J, Sakon M, Shiozaki H, Ogawa Y, Ohshiro T, Mori T: Mechanism of the haemostatic effect of ethanolamine oleate in the injection sclerotherapy for oesophageal varices. Br J Surg. 1987 Jan;74(1):50-3. [PubMed:3828735 ]
  2. Seidman E, Weber AM, Morin CL, Ethier R, Lamarche JB, Guerguerian AJ, Geoffroy G, Roy CC: Spinal cord paralysis following sclerotherapy for esophageal varices. Hepatology. 1984 Sep-Oct;4(5):950-4. [PubMed:6332769 ]
  3. Masaki M, Mitsuhashi H, Kondo Y, Suzuki S, Wada T: [Effects of embolizing agent (ethanolamine oleate; EO) on esophageal varices with special reference to endothelial injury]. Nihon Shokakibyo Gakkai Zasshi. 1984 Jun;81(6):1491. [PubMed:6471550 ]
  4. Howard ER, Stamatakis JD, Mowat AP: Management of esophageal varices in children by injection sclerotherapy. J Pediatr Surg. 1984 Feb;19(1):2-5. [PubMed:6607986 ]
  5. Zuberi BF, Baloch Q: Comparison of endoscopic variceal sclerotherapy alone and in combination with octreotide in controlling acute variceal hemorrhage and early rebleeding in patients with low-risk cirrhosis. Am J Gastroenterol. 2000 Mar;95(3):768-71. [PubMed:10710072 ]
  6. Meirelles-Santos JO, Carvalho AF Jr, Callejas-Neto F, Magna LA, Yamanaka A, Zeitune JM, Brandalise NA, Ferraz JG: Absolute ethanol and 5% ethanolamine oleate are comparable for sclerotherapy of esophageal varices. Gastrointest Endosc. 2000 May;51(5):573-6. [PubMed:10805844 ]
  7. VOIGT J: [Allergy to varex (monoethanolamine oleate)]. Ugeskr Laeger. 1954 Mar 25;116(12):452-7. [PubMed:13169341 ]
  8. VOIGT J: [Fatal allergic shock after injection of Varex (monoethanolamine-oleate). On the risks of injection treatment]. Ugeskr Laeger. 1963 Jun 21;125:896-8. [PubMed:13997698 ]
  9. PACCA ML: [Antihyaluronidase activity of monoethanolamine oleate]. Boll Soc Ital Biol Sper. 1951 Mar-Apr;27(4):576-9. [PubMed:14869471 ]
  10. NOORDIJK JA: [Monoethanolamine oleate]. Ned Tijdschr Geneeskd. 1950 Apr 22;94(16):1110-1. [PubMed:15416877 ]
  11. Yamamoto K, Sakaguchi H, Anai H, Tanaka T, Morimoto K, Kichikawa K, Uchida H: Sclerotherapy for simple cysts with use of ethanolamine oleate: preliminary experience. Cardiovasc Intervent Radiol. 2005 Nov-Dec;28(6):751-5. [PubMed:16132390 ]
  12. Takuma Y, Nouso K, Takayama H, Makino Y, Saito S, Tanaka S, Ogata M, Ohta T, Kubota J, Iwamuro M: Gastric ulcer after prophylactic balloon-occluded retrograde transvenous obliteration. J Gastroenterol. 2007 Mar;42(3):257-60. Epub 2007 Mar 30. [PubMed:17380286 ]
  13. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  14. 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 ]
  15. 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 ]
  16. 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 ]


General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
Uniprot ID:
Molecular weight:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in serine-type endopeptidase activity
Specific function:
Factor XII is a serum glycoprotein that participates in the initiation of blood coagulation, fibrinolysis, and the generation of bradykinin and angiotensin. Prekallikrein is cleaved by factor XII to form kallikrein, which then cleaves factor XII first to alpha-factor XIIa and then trypsin cleaves it to beta- factor XIIa. Alpha-factor XIIa activates factor XI to factor XIa
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Molecular weight:
  1. Takada K, Matsumoto A, Miyoshi H, Oshiba S: Changes in thrombin-antithrombin III complex after endoscopic injection sclerotherapy. Am J Gastroenterol. 1991 Jan;86(1):123-4. [PubMed:1986546 ]
  2. Kang JH, Kambayashi J, Sakon M, Shiozaki H, Ogawa Y, Ohshiro T, Mori T: Mechanism of the haemostatic effect of ethanolamine oleate in the injection sclerotherapy for oesophageal varices. Br J Surg. 1987 Jan;74(1):50-3. [PubMed:3828735 ]