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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-06-11 20:54:01 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
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
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
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified52.3 (26.2-91.7) uMNewborn (0-30 days old)BothNormal
    • Geigy Scientific ...
details
BloodDetected and Quantified1.6 (0.0-11.5) uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified14.1 +/- 3.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Cerebrospinal Fluid (CSF)Detected and Quantified8.43 (2.62-14.24) uMAdult (>18 years old)BothNormal details
UrineDetected and Quantified30.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified4.91-24.57 umol/mmol creatinineAdult (>18 years old)BothNormal
    • David F. Putnam C...
details
UrineDetected and Quantified42.75 umol/mmol creatinineAdult (>18 years old)MaleNormal
    • Shaykhutdinov RA,...
details
UrineDetected and Quantified37.1 (24.8-56.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified29.5 +/- 7.8 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified0.0028 - 0.0087 umol/mmol creatinineAdult (>18 years old)BothADPKD details
UrineDetected and Quantified31.7 +/- 6.5 umol/mmol creatinineAdult (>18 years old)Both3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency details
UrineDetected and Quantified39.7 +/- 0 umol/mmol creatinineAdult (>18 years old)BothPropionic acidemia details
UrineDetected and Quantified99.7 +/- 3.3 umol/mmol creatinineAdult (>18 years old)BothMaple syrup urine disease details
UrineDetected and Quantified51.9 +/- 0 umol/mmol creatinineAdult (>18 years old)BothAminoaciduria details
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)Download (PDF)
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

General function:
Involved in phosphatase activity
Specific function:
Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:
PHOSPHO1
Uniprot ID:
Q8TCT1
Molecular weight:
32350.505
Reactions
O-Phosphoethanolamine + Water → Ethanolamine + Phosphoric aciddetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Highly specific for ethanolamine phosphorylation. May be a rate-controlling step in phosphatidylethanolamine biosynthesis.
Gene Name:
ETNK1
Uniprot ID:
Q9HBU6
Molecular weight:
27994.955
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Involved in protein binding
Specific function:
Not Available
Gene Name:
Not Available
Uniprot ID:
Q59EA4
Molecular weight:
122007.8
General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
Reactions
Phosphatidylethanolamine + Water → Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water → 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
General function:
Involved in catalytic activity
Specific function:
Hydrolyzes lysophospholipids to produce lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine. Also can act on sphingosylphosphphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor.
Gene Name:
ENPP2
Uniprot ID:
Q13822
Molecular weight:
98992.78
Reactions
1-alkyl-sn-glycero-3-phosphoethanolamine + Water → 1-alkyl-sn-glycerol 3-phosphate + Ethanolaminedetails
1-(1-Alkenyl)-sn-glycero-3-phosphoethanolamine + Water → 1-(1-Alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
General function:
Involved in glycerophosphodiester phosphodiesterase activity
Specific function:
Has glycerophosphoinositol phosphodiesterase activity. Has little or no activity towards glycerophosphocholine. GDE1 activity can be modulated by G-protein signaling pathways (By similarity).
Gene Name:
GDE1
Uniprot ID:
Q9NZC3
Molecular weight:
37718.04
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:
CHKB
Uniprot ID:
Q9Y259
Molecular weight:
45270.99
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Highly specific for ethanolamine phosphorylation. Does not have choline kinase activity (By similarity).
Gene Name:
ETNK2
Uniprot ID:
Q9NVF9
Molecular weight:
44781.125
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Involved in calcium ion binding
Specific function:
Inhibitor of phospholipase A2, also possesses anti- coagulant properties. Also cleaves the cyclic bond of inositol 1,2-cyclic phosphate to form inositol 1-phosphate
Gene Name:
ANXA3
Uniprot ID:
P12429
Molecular weight:
36374.8
General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:
CHKA
Uniprot ID:
P35790
Molecular weight:
52248.53
Reactions
Adenosine triphosphate + Ethanolamine → ADP + O-Phosphoethanolaminedetails
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:
FAAH
Uniprot ID:
O00519
Molecular weight:
63065.28
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:
Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:
FAAH2
Uniprot ID:
Q6GMR7
Molecular weight:
58303.115
Reactions
Anandamide + Water → Arachidonic acid + Ethanolaminedetails
General function:
Involved in protein binding
Specific function:
Implicated as a critical step in numerous cellular pathways, including signal transduction, membrane trafficking, and the regulation of mitosis. May be involved in the regulation of perinuclear intravesicular membrane traffic (By similarity).
Gene Name:
PLD1
Uniprot ID:
Q13393
Molecular weight:
124183.135
Reactions
Phosphatidylethanolamine + Water → Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water → 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PLD3
Uniprot ID:
Q8IV08
Molecular weight:
54704.865
Reactions
Phosphatidylethanolamine + Water → Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water → 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PLD4
Uniprot ID:
Q96BZ4
Molecular weight:
55626.055
Reactions
Phosphatidylethanolamine + Water → Ethanolamine + Phosphatidatedetails
O-1-Alk-1-enyl-2-acyl-sn-glycero-3-phosphoethanolamine + Water → 2-Acyl-1-(1-alkenyl)-sn-glycero-3-phosphate + Ethanolaminedetails
General function:
Involved in phosphatidylserine biosynthetic process
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. In membranes, PTDSS1 catalyzes mainly the conversion of phosphatidylcholine. Also converts, in vitro and to a lesser extent, phosphatidylethanolamine.
Gene Name:
PTDSS1
Uniprot ID:
P48651
Molecular weight:
55527.18
Reactions
L-1-phosphatidylethanolamine + L-Serine → L-1-phosphatidylserine + Ethanolaminedetails
General function:
Involved in phosphatidylserine biosynthetic process
Specific function:
Catalyzes a base-exchange reaction in which the polar head group of phosphatidylethanolamine (PE) or phosphatidylcholine (PC) is replaced by L-serine. PTDSS2 is specific for phosphatatidylethanolamine and does not act on phosphatidylcholine.
Gene Name:
PTDSS2
Uniprot ID:
Q9BVG9
Molecular weight:
56252.55
Reactions
L-1-phosphatidylethanolamine + L-Serine → L-1-phosphatidylserine + Ethanolaminedetails