Bovine Metabolome Database: Showing metabocard for Ethanolamine (BMDB0000149)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:20:11 UTC

Update Date

2020-06-04 20:52:40 UTC

BMDB ID

BMDB0000149

Secondary Accession Numbers

BMDB00149

Metabolite Identification

Common Name

Ethanolamine

Description

Ethanolamine, also known as aminoethanol or glycinol, 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. Ethanolamine exists as a liquid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Ethanolamine exists in all living species, ranging from bacteria to humans. Ethanolamine is a potentially toxic compound. Ethanolamine has been found to be associated with several diseases known as perillyl alcohol administration for cancer treatment, irritable bowel syndrome, and ulcerative colitis; also ethanolamine has been linked to several inborn metabolic disorders including propionic acidemia and maple syrup urine disease.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Amino-2-hydroxyethane	ChEBI
2-Amino-1-ethanol	ChEBI
2-Amino-ethanol	ChEBI
2-Aminoethan-1-ol	ChEBI
2-Aminoethyl alcohol	ChEBI
2-Hydroxyethylamine	ChEBI
Aethanolamin	ChEBI
Aminoethanol	ChEBI
beta-Aminoethanol	ChEBI
beta-Aminoethyl alcohol	ChEBI
beta-Ethanolamine	ChEBI
beta-Hydroxyethylamine	ChEBI
Colamine	ChEBI
ETA	ChEBI
Glycinol	ChEBI
Hea	ChEBI
MEA	ChEBI
MONOETHANOLAMINE	ChEBI
b-Aminoethanol	Generator
Β-aminoethanol	Generator
b-Aminoethyl alcohol	Generator
Β-aminoethyl alcohol	Generator
b-Ethanolamine	Generator
Β-ethanolamine	Generator
b-Hydroxyethylamine	Generator
Β-hydroxyethylamine	Generator
2-Aminoethanol	HMDB
2-Ethanolamine	HMDB
2-Hydroxyethanamine	HMDB
Envision conditioner PDD 9020	HMDB
Ethylolamine	HMDB
H-Glycinol	HMDB
Monoaethanolamin	HMDB
Olamine	HMDB
2 Aminoethanol	HMDB
Ethanolamine	PhytoBank
Kolamin	PhytoBank

Chemical Formula

C₂H₇NO

Average Molecular Weight

61.0831

Monoisotopic Molecular Weight

61.052763851

IUPAC Name

2-aminoethan-1-ol

Traditional 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

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.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

1,2-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 Framework

Aliphatic acyclic compounds

External Descriptors

primary alcohol (CHEBI:16000 )
primary amine (CHEBI:16000 )
ethanolamines (CHEBI:16000 )
Biogenic amines (C00189 )
a small molecule (ETHANOL-AMINE )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Myelin sheath

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
logP	-1.5	ALOGPS
logP	-1.3	ChemAxon
logS	1.14	ALOGPS
pKa (Strongest Acidic)	15.61	ChemAxon
pKa (Strongest Basic)	9.55	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	46.25 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	16.21 m³·mol⁻¹	ChemAxon
Polarizability	6.63 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-1900000000-b64e859a0bfc46cdfcbf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-1900000000-384c99d021f0303a9d78	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-00di-1900000000-d731dd07c2dfa0287f5f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-00di-8900000000-ec4268b6041043d15437	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-00di-2900000000-02697b8ce238020537aa	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-7160c3fea0c0159e447a	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-001i-9000000000-2af16a98e43fadfa86a3	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-b64e859a0bfc46cdfcbf	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-384c99d021f0303a9d78	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-1900000000-d731dd07c2dfa0287f5f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00di-8900000000-ec4268b6041043d15437	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-00di-2900000000-02697b8ce238020537aa	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-2900000000-37831b0ceb554ca4edd2	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9000000000-e06e8502ffb0d4113432	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-001i-9100000000-e2cbdef448451ceae424	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03dl-9000000000-17dee0c07bf5cddb79ce	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-03di-9000000000-04f4c1792f8ab4f4646f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-03di-9000000000-761836be8f1018081210	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-001i-9000000000-7160c3fea0c0159e447a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positive	splash10-001i-9000000000-2af16a98e43fadfa86a3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-03di-9000000000-ae5b80bd3c5c11914ea6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0006-9000000000-6abb3d0944e188778c65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0007-9000000000-e477e52f411d933a30b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0006-9000000000-d7979261a3716365d5ae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-03di-9000000000-5c0261b2dcc6ae1291a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9000000000-ae5b80bd3c5c11914ea6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-6abb3d0944e188778c65	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0007-9000000000-e477e52f411d933a30b7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0006-9000000000-d7979261a3716365d5ae	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-03di-9000000000-5c0261b2dcc6ae1291a1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-03di-9000000000-f09b61222ca342d2835c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-3f9346b7fb6fdd5c5ce8	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-03di-9000000000-f73d8d00f0f234521971	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-eec6f92ad146ef43c111	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9000000000-9e6d219a7fbd8624cd6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01ox-9000000000-fb9020ee9b301ec7766f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-a4ae359cfcc0245b4d19	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-9000000000-b6ed81bc049b8d3042f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dl-9000000000-78c77096ed599182b5bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-f199cbf8312e0b466f1b	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-b8e7ed9f5ad724511431	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Myelin sheath

Biospecimen Locations

Brain
Epidermis
Liver
Mammary Gland
Milk
Neuron
Pancreas
Placenta
Urine

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis		Not Available
Phosphatidylethanolamine Biosynthesis		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/14:0)		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/15:0)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Brain	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Epidermis	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected and Quantified	84.09 +/- 27.64 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	323 uM	Not Specified	Not Specified	Normal	PMID: 20338431	details
Milk	Detected and Quantified	53 +/- 15 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	66 +/- 3 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	66 +/- 5 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	62 +/- 1 uM	Not Specified	Not Specified	Normal	PMID: 30994344	details
Milk	Detected and Quantified	125.81 +/- 39.77 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Milk	Detected and Quantified	116.79 +/- 23.05 uM	Not Specified	Not Specified	Normal	PMID: 29642378	details
Neuron	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Pancreas	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25599412	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000149

DrugBank ID

DB03994

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

16000

References

Synthesis Reference

Soucaille, Philippe. Ethanolamine production by fermentation of genetically modified Escherichia coli. PCT Int. Appl. (2007), 23pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Klein MS, Almstetter MF, Schlamberger G, Nurnberger N, Dettmer K, Oefner PJ, Meyer HH, Wiedemann S, Gronwald W: Nuclear magnetic resonance and mass spectrometry-based milk metabolomics in dairy cows during early and late lactation. J Dairy Sci. 2010 Apr;93(4):1539-50. doi: 10.3168/jds.2009-2563. [PubMed:20338431 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]
A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.

Enzymes

Enzyme Details

1. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2

General function:: Involved in alkylglycerophosphoethanolamine phosphodies
Specific function:: Hydrolyzes lysophospholipids to produce the signaling molecule lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine (PubMed:12119361). Also can act on sphingosylphosphorylcholine 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 (By similarity). Required for LPA production in activated platelets, cleaves the sn-1 lysophospholipids to generate sn-1 lysophosphatidic acids containing predominantly 18:2 and 20:4 fatty acids (By similarity). Shows a preference for the sn-1 to the sn-2 isomer of 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) (By similarity).
Gene Name:: ENPP2
Uniprot ID:: A1A4K5
Molecular weight:: 101717.0

Showing metabocard for Ethanolamine (BMDB0000149)

Structure for BMDB0000149 (Ethanolamine)

Enzymes