Record Information
Version1.0
Created at2020-03-19 00:25:51 UTC
Updated at2020-12-07 19:07:16 UTC
CannabisDB IDCDB000232
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nameethanolamine
DescriptionEthanolamine, 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 is a weak basic compound (based on its pKa). Ethanolamine exists in all living species, ranging from bacteria to humans and it is also present in Cannabis sativa plants (PMID: 6991645 ). Ethanolamine can be converted into O-phosphoethanolamine through the action of the enzyme choline/ethanolamine kinase. In humans, ethanolamine is involved in phosphatidylcholine biosynthesis. Ethanolamine has been detected in several different foods, such as millets, chickpea, abalones, common salsifies, and oriental wheats. Like other amines, monoethanolamine is a weak base and this property is exploited in its use in gas scrubbing. The ratio of the products can be controlled by the stoichiometry of the reactants. Reacting ethanolamine with ammonia gives ethylenediamine, a precursor of the commonly used chelating agent EDTA. It is also used in messenger molecules such as palmitoylethanolamide, which has an effect on CB1 receptors.
Structure
Thumb
Synonyms
ValueSource
1-Amino-2-hydroxyethaneChEBI
2-Amino-1-ethanolChEBI
2-Amino-ethanolChEBI
2-Aminoethan-1-olChEBI
2-Aminoethyl alcoholChEBI
2-HydroxyethylamineChEBI
AethanolaminChEBI
AminoethanolChEBI
beta-AminoethanolChEBI
beta-Aminoethyl alcoholChEBI
beta-EthanolamineChEBI
beta-HydroxyethylamineChEBI
ColamineChEBI
ETAChEBI
GlycinolChEBI
HeaChEBI
MEAChEBI
MONOETHANOLAMINEChEBI
b-AminoethanolGenerator
Β-aminoethanolGenerator
b-Aminoethyl alcoholGenerator
Β-aminoethyl alcoholGenerator
b-EthanolamineGenerator
Β-ethanolamineGenerator
b-HydroxyethylamineGenerator
Β-hydroxyethylamineGenerator
2-AminoethanolHMDB
2-EthanolamineHMDB
2-HydroxyethanamineHMDB
Envision conditioner PDD 9020HMDB
EthylolamineHMDB
H-GlycinolHMDB
MonoaethanolaminHMDB
OlamineHMDB
2 AminoethanolHMDB
EthanolaminePhytoBank
KolaminPhytoBank
Chemical FormulaC2H7NO
Average Molecular Weight61.08
Monoisotopic Molecular Weight61.0528
IUPAC Name2-aminoethan-1-ol
Traditional Nameethanolamine
CAS Registry Number9007-33-4
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
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point10.5 °CNot Available
Boiling Point170 °CWikipedia
Water Solubility1000 mg/mLNot Available
logP-1.31HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
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 Area46.25 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity16.21 m³·mol⁻¹ChemAxon
Polarizability6.63 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-b8e7ed9f5ad7245114312014-09-20View Spectrum
GC-MSethanolamine, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-b64e859a0bfc46cdfcbfSpectrum
GC-MSethanolamine, 3 TMS, GC-MS Spectrumsplash10-00di-1900000000-384c99d021f0303a9d78Spectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-d731dd07c2dfa0287f5fSpectrum
GC-MSethanolamine, 3 TMS, GC-MS Spectrumsplash10-00di-8900000000-ec4268b6041043d15437Spectrum
GC-MSethanolamine, 3 TMS, GC-MS Spectrumsplash10-00di-2900000000-02697b8ce238020537aaSpectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-7160c3fea0c0159e447aSpectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-001i-9000000000-2af16a98e43fadfa86a3Spectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-b64e859a0bfc46cdfcbfSpectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-384c99d021f0303a9d78Spectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-1900000000-d731dd07c2dfa0287f5fSpectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-8900000000-ec4268b6041043d15437Spectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-00di-2900000000-02697b8ce238020537aaSpectrum
GC-MSethanolamine, non-derivatized, GC-MS Spectrumsplash10-0fki-2900000000-37831b0ceb554ca4edd2Spectrum
Predicted GC-MSethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9000000000-e06e8502ffb0d4113432Spectrum
Predicted GC-MSethanolamine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9100000000-e2cbdef448451ceae424Spectrum
Predicted GC-MSethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSethanolamine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSethanolamine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSethanolamine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03dl-9000000000-17dee0c07bf5cddb79ce2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-9000000000-04f4c1792f8ab4f4646f2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-9000000000-761836be8f10180812102012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-001i-9000000000-7160c3fea0c0159e447a2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-68) , Positivesplash10-001i-9000000000-2af16a98e43fadfa86a32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0006-9000000000-6abb3d0944e188778c652012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-0007-9000000000-e477e52f411d933a30b72012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-0006-9000000000-d7979261a3716365d5ae2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-ae5b80bd3c5c11914ea62017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-6abb3d0944e188778c652017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0007-9000000000-e477e52f411d933a30b72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-d7979261a3716365d5ae2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-9000000000-5c0261b2dcc6ae1291a12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-03di-9000000000-f09b61222ca342d2835c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-3f9346b7fb6fdd5c5ce82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-03di-9000000000-f73d8d00f0f2345219712021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-eec6f92ad146ef43c1112021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-9000000000-9e6d219a7fbd8624cd6b2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ox-9000000000-fb9020ee9b301ec7766f2015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a4ae359cfcc0245b4d192015-05-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-9000000000-b6ed81bc049b8d3042f62015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03dl-9000000000-78c77096ed599182b5bb2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-f199cbf8312e0b466f1b2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
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)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
Phospholipase D2PLD217p13.1O14939 details
Phospholipase D1PLD13q26Q13393 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2ENPP28q24.1Q13822 details
Choline/ethanolamine kinaseCHKB22q13.33Q9Y259 details
Choline kinase alphaCHKA11q13.2P35790 details
Ethanolamine kinase 1ETNK112p12.1Q9HBU6 details
Phosphatidylserine synthase 1PTDSS18q22P48651 details
Fatty-acid amide hydrolase 1FAAH1p35-p34O00519 details
Phosphatidylserine synthase 2PTDSS211p15.5Q9BVG9 details
Phosphoethanolamine/phosphocholine phosphatasePHOSPHO117q21.32Q8TCT1 details
Ethanolamine kinase 2ETNK21q32.1Q9NVF9 details
Phospholipase D3PLD319q13.2Q8IV08 details
Phospholipase D4PLD414q32.33Q96BZ4 details
Glycerophosphodiester phosphodiesterase 1GDE116p12-p11.2Q9NZC3 details
Fatty-acid amide hydrolase 2FAAH2Xp11.21Q6GMR7 details
Phospholipase D1 variantQ59EA4 details
TransportersNot Available
Metal Bindings
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2ENPP28q24.1Q13822 details
Annexin A3ANXA34q21.21P12429 details
Phosphoethanolamine/phosphocholine phosphatasePHOSPHO117q21.32Q8TCT1 details
Glycerophosphodiester phosphodiesterase 1GDE116p12-p11.2Q9NZC3 details
Receptors
Protein NameGene NameLocusUniprot IDDetails
Phospholipase D2PLD217p13.1O14939 details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2ENPP28q24.1Q13822 details
Transcriptional Factors
Protein NameGene NameLocusUniprot IDDetails
Ectonucleotide pyrophosphatase/phosphodiesterase family member 2ENPP28q24.1Q13822 details
Concentrations Data
Not Available
HMDB IDHMDB0000149
DrugBank IDDB03994
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030851
KNApSAcK IDC00007279
Chemspider ID13835336
KEGG Compound IDC00189
BioCyc IDETHANOL-AMINE
BiGG ID34189
Wikipedia LinkEthanolamine
METLIN ID3207
PubChem Compound700
PDB IDNot Available
ChEBI ID16000
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Only showing the first 10 proteins. There are 23 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
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
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
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
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
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
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
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
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
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

Only showing the first 10 proteins. There are 23 proteins in total.