Human Metabolome Database: Showing metabocard for 2,2,2-Trichloroethanol (HMDB0041796)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (25) Show 25 proteins XML

enzymes (25) Show 25 proteins

Record Information

Version

4.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:39:48 UTC

Update Date

2019-07-23 06:35:04 UTC

HMDB ID

HMDB0041796

Secondary Accession Numbers

HMDB41796

Metabolite Identification

Common Name

2,2,2-Trichloroethanol

Description

2,2,2-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. It has, historically, been used as a sedative hypnotic. The hypnotic drug triclofos (2,2,2-trichloroethyl phosphate) is metabolized in vivo to 2,2,2-trichloroethanol. 2,2,2-Trichloroethanol is an extremely weak basic (essentially neutral) compound (based on its pKa). 2,2,2-Trichloroethanol exists in all living organisms, ranging from bacteria to humans. In humans, its pharmacological effects are similar to those of its prodrugs, chloral hydrate and chlorobutanol. Chronic exposure may result in kidney and liver damage.2,2,2-Trichloroethanol can be added to SDS-PAGE gels in order to enable fluorescent detection of proteins without a staining step. This imaging step is compatible with later analysis by, e.g., immunoblotting.2,2,2-trichloroethanol is an effective protecting group for carboxylic acids due to its ease in addition and removal. 2,2,2-Trichloroethanol is an organic compound related to ethanol, except the hydrogen atoms at position 2 are replaced with chlorine atoms.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,2,2-Trichloro-1-ethanol	ChEBI
Trichloroethanol	ChEBI
(Hydroxymethyl)trichloromethane	HMDB
2, 2,2-Trichloroethanol	HMDB
2,2,2-Trichloro-ethanol	HMDB
2,2,2-Trichloroethanol (acd/name 4.0)	HMDB
2,2,2-Trichloroethyl alcohol	HMDB
beta,beta,.beta-trichloroethanol	HMDB
beta-Trichloroethanol	HMDB
CCL3ch2oh	HMDB
Trichlorethanol	HMDB
Trichloroethyl alcohol	HMDB

Chemical Formula

C₂H₃Cl₃O

Average Molecular Weight

149.404

Monoisotopic Molecular Weight

147.924947839

IUPAC Name

2,2,2-trichloroethan-1-ol

Traditional Name

trichloroethanol

CAS Registry Number

115-20-8

SMILES

OCC(Cl)(Cl)Cl

InChI Identifier

InChI=1S/C2H3Cl3O/c3-2(4,5)1-6/h6H,1H2

InChI Key

KPWDGTGXUYRARH-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.

Kingdom

Organic compounds

Super Class

Organohalogen compounds

Class

Halohydrins

Sub Class

Chlorohydrins

Direct Parent

Chlorohydrins

Alternative Parents

Substituents

Chlorohydrin
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organochloride
Alkyl halide
Alkyl chloride
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

chloroethanol (CHEBI:28094 )
a small molecule (CPD-9673 )

Ontology

Disposition

Source:

Endogenous

Role

Biological role:

Nutrient

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	19 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	83.3 mg/mL at 25 °C	Not Available
LogP	1.42	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	16.9 g/L	ALOGPS
logP	1.23	ALOGPS
logP	1.06	ChemAxon
logS	-0.95	ALOGPS
pKa (Strongest Acidic)	12.51	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	28.22 m³·mol⁻¹	ChemAxon
Polarizability	11.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ls-4900000000-06fbb302debe717675b0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0fki-9620000000-a0dd16d8fff2e209afae	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0900000000-99ee02c6fce65a8b0921	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0900000000-c4b14f5fb152ca5bd7c3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-9500000000-bbf32ba00b1479068943	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-55cb0738d632c43cee4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-a334012ea34288f9cb8b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-03di-3900000000-c34d74c77f41759a8e5d	Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

7961

KEGG Compound ID

C07490

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2,2,2-Trichloroethanol

METLIN ID

Not Available

PubChem Compound

8259

PDB ID

Not Available

ChEBI ID

28094

Food Biomarker Ontology

Not Available

VMH ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Not Available

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

Show all enzymes and transporters

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 2B28

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'-diphosphate	details

Enzyme Details

2. UDP-glucuronosyltransferase 2B4

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'-diphosphate	details

Enzyme Details

3. UDP-glucuronosyltransferase 1-4

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'-diphosphate	details

Enzyme Details

4. UDP-glucuronosyltransferase 2B10

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'-diphosphate	details

Enzyme Details

5. UDP-glucuronosyltransferase 2B7

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'-diphosphate	details

Enzyme Details

6. UDP-glucuronosyltransferase 2B15

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'-diphosphate	details

Enzyme Details

7. UDP-glucuronosyltransferase 2A1

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'-diphosphate	details

Enzyme Details

8. UDP-glucuronosyltransferase 1-1

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'-diphosphate	details

Enzyme Details

9. UDP-glucuronosyltransferase 1-9

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'-diphosphate	details

Enzyme Details

10. UDP-glucuronosyltransferase 1-8

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'-diphosphate	details

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

Show all enzymes and transporters

Showing metabocard for 2,2,2-Trichloroethanol (HMDB0041796)

Structure for HMDB0041796 (2,2,2-Trichloroethanol)

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