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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:39:48 UTC
Update Date2019-07-23 06:35:04 UTC
HMDB IDHMDB0041796
Secondary Accession Numbers
  • HMDB41796
Metabolite Identification
Common Name2,2,2-Trichloroethanol
Description2,2,2-Trichloroethanol, also known as CCL3ch2oh or trichloroethyl alcohol, belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups. 2,2,2-Trichloroethanol exists in all living organisms, ranging from bacteria to humans. 2,2,2-Trichloroethanol has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2,2,2-trichloroethanol a potential biomarker for the consumption of these foods. 2,2,2-Trichloroethanol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 2,2,2-Trichloroethanol.
Structure
Data?1563863704
Synonyms
ValueSource
2,2,2-Trichloro-1-ethanolChEBI
TrichloroethanolChEBI
(Hydroxymethyl)trichloromethaneHMDB
2, 2,2-TrichloroethanolHMDB
2,2,2-Trichloro-ethanolHMDB
2,2,2-Trichloroethanol (acd/name 4.0)HMDB
2,2,2-Trichloroethyl alcoholHMDB
beta,beta,.beta-trichloroethanolHMDB
beta-TrichloroethanolHMDB
CCL3ch2ohHMDB
TrichlorethanolHMDB
Trichloroethyl alcoholHMDB
Chemical FormulaC2H3Cl3O
Average Molecular Weight149.404
Monoisotopic Molecular Weight147.924947839
IUPAC Name2,2,2-trichloroethan-1-ol
Traditional Nametrichloroethanol
CAS Registry Number115-20-8
SMILES
OCC(Cl)(Cl)Cl
InChI Identifier
InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2
InChI KeyKPWDGTGXUYRARH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorohydrins. These are alcohols substituted by a chlorine atom at a saturated carbon atom otherwise bearing only hydrogen or hydrocarbyl groups.
KingdomOrganic compounds
Super ClassOrganohalogen compounds
ClassHalohydrins
Sub ClassChlorohydrins
Direct ParentChlorohydrins
Alternative Parents
Substituents
  • Chlorohydrin
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organochloride
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point19 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility83.3 mg/mL at 25 °CNot Available
LogP1.42Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility16.9 g/LALOGPS
logP10(1.23) g/LALOGPS
logP10(1.06) g/LChemAxon
logS10(-0.95) g/LALOGPS
pKa (Strongest Acidic)12.51ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity28.22 m³·mol⁻¹ChemAxon
Polarizability11.25 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2,2,2-TrichloroethanolOCC(Cl)(Cl)Cl1640.7Standard polar33892256
2,2,2-TrichloroethanolOCC(Cl)(Cl)Cl821.4Standard non polar33892256
2,2,2-TrichloroethanolOCC(Cl)(Cl)Cl876.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2,2,2-Trichloroethanol,1TMS,isomer #1C[Si](C)(C)OCC(Cl)(Cl)Cl1019.8Semi standard non polar33892256
2,2,2-Trichloroethanol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC(Cl)(Cl)Cl1239.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2,2,2-Trichloroethanol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ls-4900000000-06fbb302debe717675b02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2,2-Trichloroethanol GC-MS (1 TMS) - 70eV, Positivesplash10-0fki-9620000000-a0dd16d8fff2e209afae2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2,2,2-Trichloroethanol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 10V, Positive-QTOFsplash10-0002-0900000000-99ee02c6fce65a8b09212016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 20V, Positive-QTOFsplash10-0002-0900000000-c4b14f5fb152ca5bd7c32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 40V, Positive-QTOFsplash10-001i-9500000000-bbf32ba00b14790689432016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 10V, Negative-QTOFsplash10-0002-0900000000-55cb0738d632c43cee4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 20V, Negative-QTOFsplash10-0002-0900000000-a334012ea34288f9cb8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 40V, Negative-QTOFsplash10-03di-3900000000-c34d74c77f41759a8e5d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 10V, Negative-QTOFsplash10-0002-0900000000-70bceba027b85b30fb442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 20V, Negative-QTOFsplash10-001i-9000000000-c2fa753da65a4bac80a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 40V, Negative-QTOFsplash10-0002-0900000000-70bceba027b85b30fb442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 10V, Positive-QTOFsplash10-0002-0900000000-d00629eddb575bea04722021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 20V, Positive-QTOFsplash10-0002-0900000000-4f4505ec4bcd2404fa0a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2,2,2-Trichloroethanol 40V, Positive-QTOFsplash10-03e9-7900000000-8971128a474d48910bf62021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB111662
KNApSAcK IDNot Available
Chemspider ID7961
KEGG Compound IDC07490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link2,2,2-Trichloroethanol
METLIN IDNot Available
PubChem Compound8259
PDB IDNot Available
ChEBI ID28094
Food Biomarker OntologyNot Available
VMH IDM03043
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Only showing the first 10 proteins. There are 25 proteins in total.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme has glucuronidating capacity with steroid substrates such as 5-beta-androstane 3-alpha,17-beta-diol, estradiol, ADT, eugenol and bile acids. Only isoform 1 seems to be active.
Gene Name:
UGT2B28
Uniprot ID:
Q9BY64
Molecular weight:
38742.9
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as estriol, 4-hydroxyestrone and 2-hydroxyestriol) and xenobiotics (such as 4-methylumbelliferone, 1-naphthol, 4-nitrophenol, 2-aminophenol, 4-hydroxybiphenyl and menthol). It is capable of 6 alpha-hydroxyglucuronidation of hyodeoxycholic acid.
Gene Name:
UGT2B4
Uniprot ID:
P06133
Molecular weight:
60512.035
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate.
Gene Name:
UGT1A4
Uniprot ID:
P22310
Molecular weight:
60024.535
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT2B10
Uniprot ID:
P36537
Molecular weight:
60773.485
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Its unique specificity for 3,4-catechol estrogens and estriol suggests it may play an important role in regulating the level and activity of these potent and active estrogen metabolites. Is also active with androsterone, hyodeoxycholic acid and tetrachlorocatechol (in vitro).
Gene Name:
UGT2B7
Uniprot ID:
P16662
Molecular weight:
60720.15
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xenobiotic substrates, including simple phenolic compounds, 7-hydroxylated coumarins, flavonoids, anthraquinones, and certain drugs and their hydroxylated metabolites. It also catalyzes the glucuronidation of endogenous estrogens and androgens.
Gene Name:
UGT2B15
Uniprot ID:
P54855
Molecular weight:
61035.815
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDP-glucuronosyltransferases catalyze phase II biotransformation reactions in which lipophilic substrates are conjugated with glucuronic acid to increase water solubility and enhance excretion. They are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Active on odorants and seems to be involved in olfaction; it could help clear lipophilic odorant molecules from the sensory epithelium.
Gene Name:
UGT2A1
Uniprot ID:
Q9Y4X1
Molecular weight:
60771.605
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols.
Gene Name:
UGT1A9
Uniprot ID:
O60656
Molecular weight:
59940.495
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.
Gene Name:
UGT1A8
Uniprot ID:
Q9HAW9
Molecular weight:
59741.035
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails

Only showing the first 10 proteins. There are 25 proteins in total.