Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-02-09 00:07:59 UTC
HMDB IDHMDB00149
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthanolamine
DescriptionEthanolamine is a viscous, hygroscopic amino alcohol with an ammoniacal odor. It is widely distributed in biological tissue and is a component of lecithin. It is used as a surfactant, fluorometric reagent, and to remove CO2 and H2S from natural gas and other gases.
Structure
Thumb
Synonyms
  1. 1-Amino-2-hydroxyethane
  2. 2-Amino-1-ethanol
  3. 2-Aminoethanol
  4. 2-Aminoethyl alcohol
  5. 2-Ethanolamine
  6. 2-Hydroxyethanamine
  7. 2-Hydroxyethylamine
  8. Aethanolamin
  9. Aminoethanol
  10. b-Aminoethanol
  11. b-Aminoethyl alcohol
  12. b-Ethanolamine
  13. b-Hydroxyethylamine
  14. beta-Aminoethanol
  15. beta-Aminoethyl alcohol
  16. beta-Ethanolamine
  17. beta-Hydroxyethylamine
  18. Colamine
  19. Envision Conditioner PDD 9020
  20. eta
  21. Ethanolamine
  22. Ethylolamine
  23. Glycinol
  24. H-Glycinol
  25. MEA
  26. Monoaethanolamin
  27. Monoethanolamine
  28. Olamine
Chemical FormulaC2H7NO
Average Molecular Weight61.0831
Monoisotopic Molecular Weight61.052763851
IUPAC Name2-aminoethan-1-ol
Traditional IUPAC Nameethanolamine
CAS Registry Number141-43-5
SMILES
NCCO
InChI Identifier
InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
InChI KeyHZAXFHJVJLSVMW-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAliphatic Acyclic Compounds
ClassAlkylamines
Sub Class1,2-Aminoalcohols
Other Descriptors
  • Alkylamines
  • Biogenic amines(KEGG)
  • ethanolamines(ChEBI)
Substituents
  • Primary Alcohol
Direct Parent1,2-Aminoalcohols
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point10.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000.0 mg/mLNot Available
LogP-1.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility849 g/LALOGPS
logP-1.5ALOGPS
logP-1.3ChemAxon
logS1.14ALOGPS
pKa (strongest acidic)15.61ChemAxon
pKa (strongest basic)9.55ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area46.25ChemAxon
rotatable bond count1ChemAxon
refractivity16.21ChemAxon
polarizability6.63ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Brain
  • Epidermis
  • Most Tissues
  • Myelin
  • Nerve Cells
  • Pancreas
  • Stratum Corneum
Pathways
NameSMPDB LinkKEGG Link
Phospholipid BiosynthesisSMP00025map00564
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified52.3 (26.2-91.7) uMNewborn (0-30 days old)BothNormal
  • Geigy Scient...
BloodDetected and Quantified1.6 (0.0-11.5) uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified14.1 +/- 3.0 uMAdult (>18 years old)BothNormal
  • Geigy Scient...
Cerebrospinal Fluid (CSF)Detected and Quantified8.43 (2.62-14.24) uMAdult (>18 years old)BothNormal
UrineDetected and Quantified30.9 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal
UrineDetected and Quantified4.91-24.57 umol/mmol creatinineAdult (>18 years old)BothNormal
  • David F. Put...
UrineDetected and Quantified0.0028 - 0.0087 umol/mmol creatinineAdult (>18 years old)BothNormal
UrineDetected and Quantified42.75 umol/mmol creatinineAdult (>18 years old)MaleNormal
  • Shaykhutdino...
UrineDetected and Quantified37.1 (24.8-56.2) umol/mmol creatinineAdult (>18 years old)BothCommentNormal
UrineDetected and Quantified29.5 +/- 7.8 umol/mmol creatinineAdult (>18 years old)BothNormal
  • Geigy Scient...
  • West Cadwell...
  • Basel, Switz...
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReference
UrineDetected and Quantified0.0028 - 0.0087 umol/mmol creatinineAdult (>18 years old)BothADPKD
UrineDetected and Quantified31.7 +/- 6.5 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency
UrineDetected and Quantified39.7 +/- 0 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia
UrineDetected and Quantified99.7 +/- 3.3 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease
UrineDetected and Quantified51.9 +/- 0 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03994
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB000769
KNApSAcK IDC00007279
Chemspider ID13835336
KEGG Compound IDC00189
BioCyc IDETHANOL-AMINE
BiGG ID34189
Wikipedia LinkEthanolamine
NuGOwiki LinkHMDB00149
Metagene LinkHMDB00149
METLIN ID3207
PubChem Compound700
PDB IDETA
ChEBI ID16000
References
Synthesis ReferenceSoucaille, Philippe. Ethanolamine production by fermentation of genetically modified Escherichia coli. PCT Int. Appl. (2007), 23pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. Pubmed: 12834252
  2. Denissen JF, Grabowski BA, Johnson MK, Boyd SA, Uchic JT, Stein H, Cepa S, Hill P: The orally active renin inhibitor A-74273. In vivo and in vitro morpholine ring metabolism in rats, dogs, and humans. Drug Metab Dispos. 1994 Nov-Dec;22(6):880-8. Pubmed: 7895605
  3. Vance JE: Lipoproteins secreted by cultured rat hepatocytes contain the antioxidant 1-alk-1-enyl-2-acylglycerophosphoethanolamine. Biochim Biophys Acta. 1990 Jul 16;1045(2):128-34. Pubmed: 2116174
  4. Alberghina M, Giacchetto A, Cavallaro N: Levels of ethanolamine intermediates in the human and rat visual system structures: comparison with neural tissues of a lower vertebrate (Mustelus canis) and an invertebrate (Loligo pealei). Neurochem Int. 1993 Jan;22(1):45-51. Pubmed: 8443564
  5. Hammond EJ, Uthman BM, Wilder BJ, Ben-Menachem E, Hamberger A, Hedner T, Ekman R: Neurochemical effects of vagus nerve stimulation in humans. Brain Res. 1992 Jun 26;583(1-2):300-3. Pubmed: 1504837
  6. Perschak H, Amsler U, Vischer A, Siegfried J, Cuenod M: Ventricular cerebrospinal fluid concentrations of putative amino acid transmitters in Parkinson's disease and other disorders. Hum Neurobiol. 1987;6(3):191-4. Pubmed: 2896652
  7. Renkonen O: Chromatographic separation of plasmalogenic, alkyl-acyl, and diacyl forms of ethanolamine glycerophosphatides. J Lipid Res. 1968 Jan;9(1):34-9. Pubmed: 4295349
  8. Ginsberg L, Rafique S, Xuereb JH, Rapoport SI, Gershfeld NL: Disease and anatomic specificity of ethanolamine plasmalogen deficiency in Alzheimer's disease brain. Brain Res. 1995 Nov 6;698(1-2):223-6. Pubmed: 8581486
  9. Bluml S, Seymour KJ, Ross BD: Developmental changes in choline- and ethanolamine-containing compounds measured with proton-decoupled (31)P MRS in in vivo human brain. Magn Reson Med. 1999 Oct;42(4):643-54. Pubmed: 10502752
  10. Farooqui AA, Rapoport SI, Horrocks LA: Membrane phospholipid alterations in Alzheimer's disease: deficiency of ethanolamine plasmalogens. Neurochem Res. 1997 Apr;22(4):523-7. Pubmed: 9130265
  11. Mikhaevich IS, Vlasenkova NK, Gerasimova GK: Synergistic antiproliferative effect of cis-diammine-dichloroplatinum (II) and a new anticancer agent, plasmanyl-(N-acyl)-ethanolamine, an inhibitor of protein kinase C. Biomed Sci. 1991;2(6):659-64. Pubmed: 1841636

Enzymes

Gene Name:
PLD2
Uniprot ID:
O14939
Reactions
Phosphatidylethanolamine + Water unknown Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water unknown 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
Gene Name:
PLD1
Uniprot ID:
Q13393
Reactions
Phosphatidylethanolamine + Water unknown Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water unknown 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
Gene Name:
ENPP2
Uniprot ID:
Q13822
Reactions
1-alkyl-sn-glycero-3-phosphoethanolamine + Water unknown 1-alkyl-sn-glycerol 3-phosphate + Ethanolaminedetails
1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water unknown 1-(1-Alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
Gene Name:
ANXA3
Uniprot ID:
P12429
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Reactions
Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
Gene Name:
CHKA
Uniprot ID:
P35790
Reactions
Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
Gene Name:
ETNK1
Uniprot ID:
Q9HBU6
Reactions
Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
Gene Name:
PTDSS1
Uniprot ID:
P48651
Reactions
L-1-phosphatidylethanolamine + L-Serine unknown L-1-phosphatidylserine + Ethanolaminedetails
Gene Name:
FAAH
Uniprot ID:
O00519
Reactions
Anandamide + Water unknown Arachidonic acid + Ethanolaminedetails
Gene Name:
PTDSS2
Uniprot ID:
Q9BVG9
Reactions
L-1-phosphatidylethanolamine + L-Serine unknown L-1-phosphatidylserine + Ethanolaminedetails
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Reactions
O-Phosphoethanolamine + Water unknown Ethanolamine + Phosphoric aciddetails
Gene Name:
ETNK2
Uniprot ID:
Q9NVF9
Reactions
Adenosine triphosphate + Ethanolamine unknown ADP + O-Phosphoethanolaminedetails
Gene Name:
PLD3
Uniprot ID:
Q8IV08
Reactions
Phosphatidylethanolamine + Water unknown Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water unknown 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
Gene Name:
PLD4
Uniprot ID:
Q96BZ4
Reactions
Phosphatidylethanolamine + Water unknown Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water unknown 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
Gene Name:
FAAH2
Uniprot ID:
Q6GMR7
Reactions
Anandamide + Water unknown Arachidonic acid + Ethanolaminedetails
Gene Name:
Not Available
Uniprot ID:
Q59EA4