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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-05-30 20:55:58 UTC
HMDB IDHMDB0000149
Secondary Accession Numbers
Metabolite Identification
Common NameEthanolamine
DescriptionEthanolamine (MEA), also known as monoethanolamine, aminoethanol or glycinol, belongs to the class of organic compounds known as 1,2-aminoalcohols (or simply aminoalcohols). These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Ethanolamine is a colorless, viscous liquid with an odor reminiscent of ammonia. In pharmaceutical formulations, ethanolamine is used primarily for buffering or preparation of emulsions. Ethanolamine can also be used as pH regulator in cosmetics. Biologically, ethanolamine is an initial precursor for the biosynthesis of two primary phospholipid classes, phosphatidylcholine (PC) and phosphatidylethanolamine (PE). In this regard, ethanolamine is the second-most-abundant head group for phospholipids. Ethanolamine serves as a precursor for a variety of N-acylethanolamines (NAEs). These are molecules that modulate several animal and plant physiological processes such as seed germination, plant-pathogen interactions, chloroplast development and flowering (PMID: 30190434 ). Ethanolamine, when combined with arachidonic acid (C20H32O2; 20:4, ω-6), can also form the endocannabinoid anandamide. Ethanolamine can be converted to phosphoethanolamine via the enzyme known as ethanolamine kinase. the two substrates of this enzyme are ATP and ethanolamine, whereas its two products are ADP and O-phosphoethanolamine. In most plants ethanolamine is biosynthesized by decarboxylation of serine via a pyridoxal 5'-phosphate-dependent l-serine decarboxylase (SDC). Ethanolamine exists in all living species, ranging from bacteria to plants to humans. Ethanolamine has been detected, but not quantified in, several different foods, such as narrowleaf cattails, mung beans, blackcurrants, white cabbages, and bilberries.
Structure
Thumb
Synonyms
Chemical FormulaC2H7NO
Average Molecular Weight61.0831
Monoisotopic Molecular Weight61.052763851
IUPAC Name2-aminoethan-1-ol
Traditional 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
Description Belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct Parent1,2-aminoalcohols
Alternative Parents
Substituents
  • 1,2-aminoalcohol
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Primary aliphatic amine
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Naturally occurring process
Role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point10.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1000 mg/mLNot Available
LogP-1.31HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Breast Milk
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Locations
  • Brain
  • Epidermis
  • Neuron
  • Pancreas
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Perillyl alcohol administration for cancer treatment
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Pancreatic cancer
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Periodontal disease
  1. Sugimoto M, Wong DT, Hirayama A, Soga T, Tomita M: Capillary electrophoresis mass spectrometry-based saliva metabolomics identified oral, breast and pancreatic cancer-specific profiles. Metabolomics. 2010 Mar;6(1):78-95. Epub 2009 Sep 10. [PubMed:20300169 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Propionic acidemia
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Maple syrup urine disease
  1. Gronwald W, Klein MS, Kaspar H, Fagerer SR, Nurnberger N, Dettmer K, Bertsch T, Oefner PJ: Urinary metabolite quantification employing 2D NMR spectroscopy. Anal Chem. 2008 Dec 1;80(23):9288-97. doi: 10.1021/ac801627c. [PubMed:19551947 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Ethanolaminuria
  1. Cole DE, Farag S, Dooley KC: Ethanolaminuria: a non-specific laboratory finding in the seriously ill infant. Clin Biochem. 1988 Oct;21(5):297-300. [PubMed:3233740 ]
Associated OMIM IDs
DrugBank IDDB03994
Phenol Explorer Compound IDNot Available
FooDB IDFDB030851
KNApSAcK IDC00007279
Chemspider ID13835336
KEGG Compound IDC00189
BioCyc IDETHANOL-AMINE
BiGG ID34189
Wikipedia LinkEthanolamine
METLIN ID3207
PubChem Compound700
PDB IDNot Available
ChEBI ID16000
Food Biomarker OntologyNot Available
VMH IDETHA
MarkerDB IDMDB00000071
Good Scents IDNot Available
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

Only showing the first 10 proteins. There are 17 proteins in total.

Enzymes

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 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:
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 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. 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:
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:
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 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 + Serine → L-1-phosphatidylserine + 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 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 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 + Serine → L-1-phosphatidylserine + Ethanolaminedetails

Only showing the first 10 proteins. There are 17 proteins in total.