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Showing metabocard for Triclosan (HMDB0061385)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2013-12-17 17:00:44 UTC
Update Date2020-11-09 23:21:49 UTC
HMDB IDHMDB0061385
Secondary Accession Numbers
  • HMDB61385
Metabolite Identification
Common NameTriclosan
DescriptionTriclosan is an antibacterial and antifungal agent. It is a polychloro phenoxy phenol. It is widely used as a preservative and antimicrobial agent in personal care products such as soaps, skin creams, toothpaste and deodorants as well as in household items such as plastic chopping boards, sports equipment and shoes. According to the Food and Drug Administration (FDA) at the present time there is no evidence that triclosan in personal care products provides an extra benefit to health beyond its anti-gingivitis effect in toothpaste. The FDA does not recommend changing consumer use of triclosan containing products one way or the other due to currently insufficient safety evidence. Studies by the Environmental Protection Agency (EPA) found triclosan to be an effective antibacterial. Triclosan safety is currently under review by the FDA and Health Canada. Triclosan is only found in individuals that have used or taken this drug. 
Structure
Data?1563866179
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2,4,4'-Trichloro-2'-hydroxydiphenyl etherChEBI
5-Chloro-2-(2,4-dichloro-phenoxy)-phenolChEBI
TriclosanumChEBI
Stri-dex cleansing barKegg
AquaseptHMDB
Irgasan DP 300HMDB
2-Hydroxy-2',4,4'-trichlorodiphenyl etherHMDB
Pharmachem brand OF triclosanHMDB
Procter and gamble brand OF triclosanHMDB
TersasepticHMDB
GlaxoSmithKline brand OF triclosanHMDB
Irgasan DP300HMDB
Irgasan-DP300HMDB
SapodermHMDB
SterZac bath concentrateHMDB
TrisanHMDB
Triclosan pharmachem brandHMDB
Clearasil daily face washHMDB
ClinicleanHMDB
DP300, IrgasanHMDB
Dermtek brand OF triclosanHMDB
Johnson and johnson brand OF triclosanHMDB
ManuseptHMDB
Microshield THMDB
Oxy skin washHMDB
Reckitt brand OF triclosanHMDB
SSL Brand OF triclosanHMDB
Ster zac bath concentrateHMDB
Ster-zac bath concentrateHMDB
trans Canaderm brand OF triclosanHMDB
Triclosan reckitt brandHMDB
PHisoHexHMDB
Chemical FormulaC12H7Cl3O2
Average Molecular Weight289.542
Monoisotopic Molecular Weight287.951162589
IUPAC Name5-chloro-2-(2,4-dichlorophenoxy)phenol
Traditional Nametriclosan
CAS Registry Number3380-34-5
SMILES
OC1=CC(Cl)=CC=C1OC1=C(Cl)C=C(Cl)C=C1
InChI Identifier
InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H
InChI KeyXEFQLINVKFYRCS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as diphenylethers. These are aromatic compounds containing two benzene rings linked to each other through an ether group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassDiphenylethers
Direct ParentDiphenylethers
Alternative Parents
Substituents
  • Diphenylether
  • Diaryl ether
  • Phenoxy compound
  • Phenol ether
  • 1,3-dichlorobenzene
  • 3-chlorophenol
  • 3-halophenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Ether
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Route of exposure:

Biological location:

Role

Environmental role:

Industrial application:

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 Solubility0.006 g/LALOGPS
logP5.53ALOGPS
logP4.98ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)7.68ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity68.69 m³·mol⁻¹ChemAxon
Polarizability25.92 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-0490000000-dfb0757bfac1ad90e7a4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9468000000-8ac957d92fb0baadf85dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-58c362c848ddc0ea6b7dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-d33e377d9d635f1ce853Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-0006-0900000000-86a497478420de6dd62bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01ox-1900000000-3924bb3259de13cc0c32Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-01p9-9500000000-1eea0ef329f1eda65753Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-9000000000-c0811786de4d26d32f19Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1e8f398c881d4511de15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-0udi-0090000000-1e8f398c881d4511de15Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0090000000-901f5a26f0a84efe9ab9Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-000i-0190000000-665be7c9535346c9a726Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-7662f8b4bedcaffe0a5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-62befab95441bb9ec2f0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udj-3980000000-375beaf060515d4bc75bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-0a0e87adf47e90d9ec1bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-40be759356bf6e86ef46Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ikc-2980000000-85ef168fbb3f3d0db80aSpectrum
MSMass Spectrum (Electron Ionization)splash10-029g-9780000000-d39624d358bdeff3e131Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Breast Milk
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.000249 uMAdult (>18 years old)FemaleNormal details
BloodDetected and Quantified0.0553 uMAdult (>18 years old)Female
Normal		 details
BloodDetected and Quantified0.00173 +/- 0.00294 uMAdult (>18 years old)BothN/A details
BloodDetected and Quantified0.0038 +/- 0.00415 uMAdult (>18 years old)BothN/A details
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Breast MilkDetected and Quantified0.0000656 uMAdult (>18 years old)Female
Normal		 details
Breast MilkDetected and Quantified0.00187 uMAdult (>18 years old)Female
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.00387 (0.00289-0.0052) umol/mmol creatinineChildren (1-13 years old)Not Specified
N/A		 details
UrineDetected and Quantified0.00426 (0.00324-0.00555) umol/mmol creatinineAdolescent (13-18 years old)Not Specified
N/A		 details
UrineDetected and Quantified0.00539 (0.00485-0.00598) umol/mmol creatinineAdult (>18 years old)Not Specified
N/A		 details
UrineDetected and Quantified0.00485 (0.00379-0.00621) umol/mmol creatinineElderly (>65 years old)Not Specified
N/A		 details
UrineDetected and Quantified0.00481 (0.00414-0.00555) umol/mmol creatinineNot SpecifiedFemale
N/A		 details
UrineDetected and Quantified0.0052 (0.00442-0.0061) umol/mmol creatinineNot SpecifiedMale
N/A		 details
UrineDetected and Quantified0.00640 (0.00535-0.00773) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
UrineDetected and Quantified0.00554 (0.00484-0.00640) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08604
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC12059
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTriclosan
METLIN IDNot Available
PubChem Compound5564
PDB IDNot Available
ChEBI ID164200
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00029827
References
Synthesis ReferenceMichael A. Mitchell, “Process For Producing Triclosan-Coated Superabsorbents.” U.S. Patent US20120157302, issued June 21, 2012.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. Epub 2004 Apr 8. [PubMed:15073159 ]
  2. Heath RJ, Rubin JR, Holland DR, Zhang E, Snow ME, Rock CO: Mechanism of triclosan inhibition of bacterial fatty acid synthesis. J Biol Chem. 1999 Apr 16;274(16):11110-4. [PubMed:10196195 ]
  3. Fan F, Yan K, Wallis NG, Reed S, Moore TD, Rittenhouse SF, DeWolf WE Jr, Huang J, McDevitt D, Miller WH, Seefeld MA, Newlander KA, Jakas DR, Head MS, Payne DJ: Defining and combating the mechanisms of triclosan resistance in clinical isolates of Staphylococcus aureus. Antimicrob Agents Chemother. 2002 Nov;46(11):3343-7. [PubMed:12384334 ]
  4. Moss T, Howes D, Williams FM: Percutaneous penetration and dermal metabolism of triclosan (2,4, 4'-trichloro-2'-hydroxydiphenyl ether). Food Chem Toxicol. 2000 Apr;38(4):361-70. [PubMed:10722890 ]
  5. Fang JL, Stingley RL, Beland FA, Harrouk W, Lumpkins DL, Howard P: Occurrence, efficacy, metabolism, and toxicity of triclosan. J Environ Sci Health C Environ Carcinog Ecotoxicol Rev. 2010 Jul;28(3):147-71. doi: 10.1080/10590501.2010.504978. [PubMed:20859822 ]
  6. ON THE FATE OF TRICLOSAN IN HUMANS [Link]

Enzymes

Enzyme Details
1. Sulfotransferase 1A1
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of catecholamines, phenolic drugs and neurotransmitters. Has also estrogen sulfotransferase activity. responsible for the sulfonation and activation of minoxidil. Is Mediates the metabolic activation of carcinogenic N-hydroxyarylamines to DNA binding products and could so participate as modulating factor of cancer risk.
Gene Name:
SULT1A1
Uniprot ID:
P50225
Molecular weight:
34165.13
References
  1. Wang LQ, Falany CN, James MO: Triclosan as a substrate and inhibitor of 3'-phosphoadenosine 5'-phosphosulfate-sulfotransferase and UDP-glucuronosyl transferase in human liver fractions. Drug Metab Dispos. 2004 Oct;32(10):1162-9. Epub 2004 Jul 21. [PubMed:15269185 ]
Enzyme Details
2. Estrogen sulfotransferase
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of estradiol and estrone. May play a role in the regulation of estrogen receptor activity by metabolizing free estradiol. Maximally sulfates beta-estradiol and estrone at concentrations of 20 nM. Also sulfates dehydroepiandrosterone, pregnenolone, ethinylestradiol, equalenin, diethylstilbesterol and 1-naphthol, at significantly higher concentrations; however, cortisol, testosterone and dopamine are not sulfated.
Gene Name:
SULT1E1
Uniprot ID:
P49888
Molecular weight:
35126.185
References
  1. Wang LQ, Falany CN, James MO: Triclosan as a substrate and inhibitor of 3'-phosphoadenosine 5'-phosphosulfate-sulfotransferase and UDP-glucuronosyl transferase in human liver fractions. Drug Metab Dispos. 2004 Oct;32(10):1162-9. Epub 2004 Jul 21. [PubMed:15269185 ]
Enzyme Details
3. 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
References
  1. Wang LQ, Falany CN, James MO: Triclosan as a substrate and inhibitor of 3'-phosphoadenosine 5'-phosphosulfate-sulfotransferase and UDP-glucuronosyl transferase in human liver fractions. Drug Metab Dispos. 2004 Oct;32(10):1162-9. Epub 2004 Jul 21. [PubMed:15269185 ]