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Record Information
Version3.6
Creation Date2012-09-13 11:56:01 UTC
Update Date2016-02-11 03:55:39 UTC
HMDB IDHMDB42049
Secondary Accession NumbersNone
Metabolite Identification
Common NameTrichloroethanol glucuronide
DescriptionTrichloroethanol glucuronide belongs to the family of Glucuronic Acid Derivatives. These are compounds containing a glucuronic acid moeity (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
Structure
Thumb
Synonyms
ValueSource
Urochloralic acidKegg
2,2,2-Trichloroethyl beta-D-glucopyranosiduronic acidKegg
UrochloralateGenerator
2,2,2-Trichloroethyl b-D-glucopyranosiduronateGenerator
2,2,2-Trichloroethyl b-D-glucopyranosiduronic acidGenerator
2,2,2-Trichloroethyl beta-D-glucopyranosiduronateGenerator
2,2,2-Trichloroethyl β-D-glucopyranosiduronateGenerator
2,2,2-Trichloroethyl β-D-glucopyranosiduronic acidGenerator
Chemical FormulaC8H11Cl3O7
Average Molecular Weight325.528
Monoisotopic Molecular Weight323.957035827
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(2,2,2-trichloroethoxy)oxane-2-carboxylic acid
Traditional Nametrichloroethanol glucuronide
CAS Registry Number97-25-6
SMILES
O[C@@H]1[C@@H](O)[C@H](OCC(Cl)(Cl)Cl)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1/C8H11Cl3O7/c9-8(10,11)1-17-7-4(14)2(12)3(13)5(18-7)6(15)16/h2-5,7,12-14H,1H2,(H,15,16)/t2-,3-,4+,5-,7+/s2
InChI KeyInChIKey=IQOASJJGUQMXDW-ZOPYGRBCNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar acids and derivatives
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • O-glucuronide
  • 1-o-glucuronide
  • O-glycosyl compound
  • Glycosyl compound
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Beta-hydroxy acid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alkyl halide
  • Alkyl chloride
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Nutrient
  • Waste products
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point142 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility15.9 mg/mLALOGPS
logP-0.13ALOGPS
logP-0.39ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.21ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area116.45 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity60.5 m3·mol-1ChemAxon
Polarizability26.81 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Kidney
  • Liver
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2300807
KEGG Compound IDC14869
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB42049
Metagene LinkHMDB42049
METLIN IDNot Available
PubChem Compound3036914
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

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
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:
UGT1A3
Uniprot ID:
P35503
Molecular weight:
60337.835
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:
UGT1A10
Uniprot ID:
Q9HAW8
Molecular weight:
59809.075
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. The major substrates of this isozyme are eugenol > 4-methylumbelliferone > dihydrotestosterone (DHT) > androstane-3-alpha,17-beta-diol (3-alpha-diol) > testosterone > androsterone (ADT).
Gene Name:
UGT2B17
Uniprot ID:
O75795
Molecular weight:
61094.915
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:
UGT1A6
Uniprot ID:
P19224
Molecular weight:
60750.215
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:
UGT1A5
Uniprot ID:
P35504
Molecular weight:
60070.565
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:
UGT2B11
Uniprot ID:
O75310
Molecular weight:
61037.8
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:
UGT1A7
Uniprot ID:
Q9HAW7
Molecular weight:
59818.315
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 (By similarity).
Gene Name:
UGT2A3
Uniprot ID:
Q6UWM9
Molecular weight:
60253.94
Reactions
2,2,2-Trichloroethanol + Uridine diphosphate glucuronic acid → Trichloroethanol glucuronide + Uridine 5'-diphosphatedetails