Basic Info

Common NameTriethanolamine(F05537)
2D Structure
Description

Triethanolamine is used as a food additive [EAFUS] ("EAFUS: Everything Added to Food in the United States. [http://www.eafus.com/]").

Triethanolamine belongs to the family of Alkylamines. These are organic compounds containing an alkylamine group.

FRCD IDF05537
CAS Number102-71-6
PubChem CID7618
FormulaC6H15NO3
IUPAC Name

2-[bis(2-hydroxyethyl)amino]ethanol

InChI Key

GSEJCLTVZPLZKY-UHFFFAOYSA-N

InChI

InChI=1S/C6H15NO3/c8-4-1-7(2-5-9)3-6-10/h8-10H,1-6H2

Canonical SMILES

C(CO)N(CCO)CCO

Isomeric SMILES

C(CO)N(CCO)CCO

Synonyms
        
            TRIETHANOLAMINE
        
            Trolamine
        
            102-71-6
        
            2,2',2''-Nitrilotriethanol
        
            Sterolamide
        
            Daltogen
        
            Tris(2-hydroxyethyl)amine
        
            Triethylolamine
        
            Nitrilotriethanol
        
            Trihydroxytriethylamine
        
Classifies
                

                  
                    Predicted: Pesticide
                  

                
        
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic nitrogen compounds
ClassOrganonitrogen compounds
SubclassAmines
Intermediate Tree NodesAlkanolamines
Direct Parent1,2-aminoalcohols
Alternative Parents
Molecular FrameworkAliphatic acyclic compounds
SubstituentsTertiary aliphatic amine - Tertiary amine - 1,2-aminoalcohol - Organic oxygen compound - Organopnictogen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound
DescriptionThis compound 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.

Properties

Property NameProperty Value
Molecular Weight149.19
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count4
Rotatable Bond Count6
Complexity55.7
Monoisotopic Mass149.105
Exact Mass149.105
XLogP-1
Formal Charge0
Heavy Atom Count10
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB-0.6079
Human Intestinal AbsorptionHIA+0.8898
Caco-2 PermeabilityCaco2+0.5310
P-glycoprotein SubstrateNon-substrate0.5737
P-glycoprotein InhibitorNon-inhibitor0.8976
Non-inhibitor0.7496
Renal Organic Cation TransporterNon-inhibitor0.7135
Distribution
Subcellular localizationLysosome0.6735
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8296
CYP450 2D6 SubstrateNon-substrate0.7688
CYP450 3A4 SubstrateNon-substrate0.7720
CYP450 1A2 InhibitorNon-inhibitor0.9251
CYP450 2C9 InhibitorNon-inhibitor0.9129
CYP450 2D6 InhibitorNon-inhibitor0.9227
CYP450 2C19 InhibitorNon-inhibitor0.9296
CYP450 3A4 InhibitorNon-inhibitor0.9370
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9507
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.5307
Non-inhibitor0.8578
AMES ToxicityNon AMES toxic0.9132
CarcinogensNon-carcinogens0.6875
Fish ToxicityLow FHMT0.9197
Tetrahymena Pyriformis ToxicityLow TPT0.9911
Honey Bee ToxicityLow HBT0.6081
BiodegradationNot ready biodegradable0.7276
Acute Oral ToxicityIV0.6306
Carcinogenicity (Three-class)Non-required0.6947

Model Value Unit
Absorption
Aqueous solubility-0.1445LogS
Caco-2 Permeability0.8443LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity1.4624LD50, mol/kg
Fish Toxicity3.9470pLC50, mg/L
Tetrahymena Pyriformis Toxicity-1.6247pIGC50, ug/L

References

TitleJournalDatePubmed ID
Potentially toxic elements (PTEs) in soils from the surroundings of the Trans-Amazonian Highway, Brazil.Environ Monit Assess2015 Jan25391461
Surfactants, aromatic and isoprenoid compounds, and fatty acid biosynthesis inhibitors suppress Staphylococcus aureus production of toxic shock syndrome toxin 1.Antimicrob Agents Chemother2009 May19223628
Absorption, distribution, metabolism and excretion of intravenously and dermally administered triethanolamine in mice.Food Chem Toxicol2000 Nov11038241

Targets

General Function:
Zinc ion binding
Specific Function:
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleylethanolamide, a naturally occurring lipid that regulates satiety. Receptor for peroxisome proliferators such as hypolipidemic drugs and fatty acids. Regulates the peroxisomal beta-oxidation pathway of fatty acids. Functions as transcription activator for the ACOX1 and P450 genes. Transactivation activity requires heterodimerization with RXRA and is antagonized by NR2C2. May be required for the propagation of clock information to metabolic pathways regulated by PER2.
Gene Name:
PPARA
Uniprot ID:
Q07869
Molecular Weight:
52224.595 Da
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]