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Human Metabolome Database Version 3.5

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Showing metabocard for Ethanolamine (HMDB00149)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:07:59 -0700
HMDB ID HMDB00149
Secondary Accession Numbers None
Metabolite Identification
Common Name Ethanolamine
Description Ethanolamine 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C2H7NO
Average Molecular Weight 61.0831
Monoisotopic Molecular Weight 61.052763851
IUPAC Name 2-aminoethan-1-ol
Traditional IUPAC Name ethanolamine
CAS Registry Number 141-43-5
SMILES NCCO
InChI Identifier InChI=1S/C2H7NO/c3-1-2-4/h4H,1-3H2
InChI Key HZAXFHJVJLSVMW-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aliphatic Acyclic Compounds
Class Alkylamines
Sub Class 1,2-Aminoalcohols
Other Descriptors
  • Alkylamines
  • Biogenic amines(KEGG)
  • ethanolamines(ChEBI)
Substituents
  • Primary Alcohol
Direct Parent 1,2-Aminoalcohols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
Biofunction
  • Component of Glycerophospholipid metabolism
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Liquid
Experimental Properties
Property Value Reference
Melting Point 10.5 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 1000.0 mg/mL Not Available
LogP -1.31 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 849 g/L ALOGPS
LogP -1.53 ALOGPS
LogP -1.3 ChemAxon
LogS 1.14 ALOGPS
pKa (strongest acidic) 15.61 ChemAxon
pKa (strongest basic) 9.55 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 46.25 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 16.21 ChemAxon
Polarizability 6.63 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
13C NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (HITACHI M-68)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 50
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Urine
Tissue Location
  • Most Tissues
  • Pancreas
  • Epidermis
  • Brain
  • Myelin
  • Nerve Cells
  • Stratum Corneum
Pathways
Name SMPDB Link KEGG Link
Phospholipid Biosynthesis SMP00025 map00564 Link_out
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
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52.3 (26.2-91.7) uM Newborn (0-30 days old) Both Normal Not Available
Blood Detected and Quantified
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1.6 (0.0-11.5) uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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14.1 +/- 3.0 uM Adult (>18 years old) Both Normal Not Available
Cerebrospinal Fluid (CSF) Detected and Quantified
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8.43 (2.62-14.24) uM Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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30.9 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and not Quantified
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Not Applicable Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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4.91-24.57 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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0.0028 - 0.0087 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Urine Detected and Quantified
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42.75 umol/mmol creatinine Adult (>18 years old) Male Normal Not Available
Urine Detected and Quantified
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37.1 (24.8-56.2) umol/mmol creatinine Adult (>18 years old) Both Normal urine by NMR
Urine Detected and Quantified
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29.5 +/- 7.8 umol/mmol creatinine Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Comments
Urine Detected and Quantified
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0.0028 - 0.0087 umol/mmol creatinine Adult (>18 years old) Both ADPKD Not Available
Urine Detected and Quantified
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31.7 +/- 6.5 umol/mmol creatinine Adult (>18 years old) Both 3-Hydroxy-3- methylglutaryl-CoA lyase (HL) deficency Not Available
Urine Detected and Quantified
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39.7 +/- 0 umol/mmol creatinine Adult (>18 years old) Both Propionic acidemia Not Available
Urine Detected and Quantified
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99.7 +/- 3.3 umol/mmol creatinine Adult (>18 years old) Both Maple syrup urine disease Not Available
Urine Detected and Quantified
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51.9 +/- 0 umol/mmol creatinine Adult (>18 years old) Both Aminoaciduria Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB03994 Link_out
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB000769
KNApSAcK ID C00007279 Link_out
Chemspider ID 13835336 Link_out
KEGG Compound ID C00189 Link_out
BioCyc ID ETHANOL-AMINE Link_out
BiGG ID 34189 Link_out
Wikipedia Link Ethanolamine Link_out
NuGOwiki Link HMDB00149 Link_out
Metagene Link HMDB00149 Link_out
METLIN ID 3207 Link_out
PubChem Compound 700 Link_out
PDB ID ETA Link_out
ChEBI ID 16000 Link_out
References
Synthesis Reference Soucaille, 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. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. 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 Link_out
  7. 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 Link_out
  8. 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 Link_out
  9. 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 Link_out
  10. 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 Link_out
  11. 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 Link_out
Enzymes
Name: Phospholipase D2
Reactions:
  • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
Reactions:
  • 1-alkyl-sn-glycero-3-phosphoethanolamine + H2O = 1-alkyl-sn-glycerol 3-phosphate + ethanolamine [RN:R04362]
Gene Name: ENPP2
Uniprot ID: Q13822 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Annexin A3
Reactions:
    Gene Name: ANXA3
    Uniprot ID: P12429 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Choline/ethanolamine kinase
    Reactions:
    • ATP + ethanolamine = ADP + O-phosphoethanolamine [RN:R01468]
    Gene Name: CHKB
    Uniprot ID: Q9Y259 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ethanolamine kinase 1
    Reactions:
    • ATP + ethanolamine = ADP + O-phosphoethanolamine [RN:R01468]
    Gene Name: ETNK1
    Uniprot ID: Q9HBU6 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phosphoethanolamine/phosphocholine phosphatase
    Reactions:
    • (1) O-phosphoethanolamine + H2O = ethanolamine + phosphate [RN:R06870]
    • (2) phosphocholine + H2O = choline + phosphate [RN:R06871]
    Gene Name: PHOSPHO1
    Uniprot ID: Q8TCT1 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Ethanolamine kinase 2
    Reactions:
    • ATP + ethanolamine = ADP + O-phosphoethanolamine [RN:R01468]
    Gene Name: ETNK2
    Uniprot ID: Q9NVF9 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Glycerophosphodiester phosphodiesterase 1
    Reactions:
    • 1-(sn-glycero-3-phospho)-1D-myo-inositol + H2O = myo-inositol + sn-glycerol 3-phosphate [RN:R01193]
    Gene Name: GDE1
    Uniprot ID: Q9NZC3 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phospholipase D1 variant
    Reactions:
      Gene Name: Not Available
      Uniprot ID: Q59EA4 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA