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Record Information
Version3.6
Creation Date2013-12-19 18:49:33 UTC
Update Date2016-02-11 08:19:55 UTC
HMDB IDHMDB61386
Secondary Accession NumbersNone
Metabolite Identification
Common NameTriclosan glucuronide
DescriptionTriclosan glucuronide is a metabolite of the bacteriostat, Triclosan. Triclosan is metabolized to the glucuronide, and to the sulfate. Triclosan is an antibacterial and antifungal agent. It is a polychloro phenoxy phenol. It is present in soaps, shampoos, deodorants, toothpastes, mouth washes, and cleaning supplies. Triclosan has been shown to be effective in reducing and controlling bacterial contamination on the hands and on treated products. (Wikipedia)
Structure
Thumb
Synonyms
ValueSource
5-chloro-2-(2,4-Dichlorophenoxy)phenyl β-D-glucopyranosiduronic acidHMDB
Irgasan DP 300 glucuronideHMDB
Triclosan O-beta-D-glucuronideHMDB
Chemical FormulaC18H15Cl3O8
Average Molecular Weight465.666
Monoisotopic Molecular Weight463.983250577
IUPAC Name(2S,3S,4S,5R,6S)-6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6S)-6-[5-chloro-2-(2,4-dichlorophenoxy)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CAS Registry Number63156-12-7
SMILES
O[C@@H]1[C@@H](O)[C@H](OC2=CC(Cl)=CC=C2OC2=C(Cl)C=C(Cl)C=C2)O[C@@H]([C@H]1O)C(O)=O
InChI Identifier
InChI=1/C18H15Cl3O8/c19-7-1-3-10(9(21)5-7)27-11-4-2-8(20)6-12(11)28-18-15(24)13(22)14(23)16(29-18)17(25)26/h1-6,13-16,18,22-24H,(H,25,26)/t13-,14-,15+,16-,18+/s2
InChI KeyInChIKey=DNYVWBJVOYZRCX-ZGIMUMDFNA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct ParentPhenolic glycosides
Alternative Parents
Substituents
  • Phenolic glycoside
  • O-glucuronide
  • 1-o-glucuronide
  • Diphenylether
  • Glucuronic acid or derivatives
  • O-glycosyl compound
  • Diaryl ether
  • Pyran carboxylic acid
  • Pyran carboxylic acid or derivatives
  • Phenol ether
  • 1,3-dichlorobenzene
  • Halobenzene
  • Chlorobenzene
  • Beta-hydroxy acid
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.14 mg/mLALOGPS
logP2.94ALOGPS
logP3.03ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)2.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity100.71 m3·mol-1ChemAxon
Polarizability41.34 Å3ChemAxon
Number of Rings3ChemAxon
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
  • Skin
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
N/A
details
UrineDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
N/A
details
UrineDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
N/A
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 IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB61386
Metagene LinkHMDB61386
METLIN IDNot Available
PubChem Compound71752714
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available