MiMeDB: Showing metabocard for 2,4,4'-trichloro-2'-hydroxydiphenylethe (MMDBc0012204)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 03:48:32 UTC

Update Date

2024-09-29 07:41:02 UTC

Metabolite ID

MMDBc0012204

Metabolite Identification

Common Name

2,4,4'-trichloro-2'-hydroxydiphenylethe

Description

Triclosan 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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 12161323002D          

 17 18  0  0  0  0            999 V2000
    3.8167   -0.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -1.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -1.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2375   -0.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9542   -1.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1042   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -2.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -2.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9625   -1.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792    0.0583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.2291    0.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -2.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2417   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542   -2.4250    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.6792   -2.4042    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  8  2  0  0  0  0
 15  9  1  0  0  0  0
 16 10  1  0  0  0  0
 17 11  1  0  0  0  0
  7 11  1  0  0  0  0
  6 10  2  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0012204

> <DATABASE_NAME>
MIME

> <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_KEY>
XEFQLINVKFYRCS-UHFFFAOYSA-N

> <FORMULA>
C12H7Cl3O2

> <MOLECULAR_WEIGHT>
289.542

> <EXACT_MASS>
287.951162589

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.924013696911807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-2-(2,4-dichlorophenoxy)phenol

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
4.982101706333333

> <ALOGPS_LOGS>
-4.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.680637141111775

> <JCHEM_PKA_STRONGEST_BASIC>
-6.674592364029308

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
68.6941

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triclosan

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 16-DEC-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-DEC-13         0                                  
HETATM    1  O   UNK     0       7.125  -1.431   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.795  -2.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.455  -2.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.441  -1.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.777  -1.408   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.127  -2.217   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.115  -2.170   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.795  -3.757   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.455  -3.733   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.127  -3.757   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.130  -3.718   0.000  0.00  0.00           C+0
HETATM   12 Cl   UNK     0       4.441   0.109   0.000  0.00  0.00          Cl+0
HETATM   13  O   UNK     0       9.761   0.117   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.441  -4.527   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.785  -4.488   0.000  0.00  0.00           C+0
HETATM   16 Cl   UNK     0       1.781  -4.527   0.000  0.00  0.00          Cl+0
HETATM   17 Cl   UNK     0      12.468  -4.488   0.000  0.00  0.00          Cl+0
CONECT    1    2    3                                                       
CONECT    2    1    4    8                                                  
CONECT    3    1    5    9                                                  
CONECT    4    2    6   12                                                  
CONECT    5    3    7   13                                                  
CONECT    6    4   10                                                       
CONECT    7    5   11                                                       
CONECT    8    2   14                                                       
CONECT    9    3   15                                                       
CONECT   10   14   16    6                                                  
CONECT   11   15   17    7                                                  
CONECT   12    4                                                            
CONECT   13    5                                                            
CONECT   14   10    8                                                       
CONECT   15   11    9                                                       
CONECT   16   10                                                            
CONECT   17   11                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

Synonyms

Value	Source
2,4,4'-Trichloro-2'-hydroxydiphenyl ether	ChEBI
5-Chloro-2-(2,4-dichloro-phenoxy)-phenol	ChEBI
Triclosanum	ChEBI
Stri-dex cleansing bar	Kegg
Aquasept	HMDB
Irgasan DP 300	HMDB
2-Hydroxy-2',4,4'-trichlorodiphenyl ether	HMDB
Pharmachem brand OF triclosan	HMDB
Procter and gamble brand OF triclosan	HMDB
Tersaseptic	HMDB
GlaxoSmithKline brand OF triclosan	HMDB
Irgasan DP300	HMDB
Irgasan-DP300	HMDB
Sapoderm	HMDB
SterZac bath concentrate	HMDB
Trisan	HMDB
Triclosan pharmachem brand	HMDB
Clearasil daily face wash	HMDB
Cliniclean	HMDB
DP300, Irgasan	HMDB
Dermtek brand OF triclosan	HMDB
Johnson and johnson brand OF triclosan	HMDB
Manusept	HMDB
Microshield T	HMDB
Oxy skin wash	HMDB
Reckitt brand OF triclosan	HMDB
SSL Brand OF triclosan	HMDB
Ster zac bath concentrate	HMDB
Ster-zac bath concentrate	HMDB
trans Canaderm brand OF triclosan	HMDB
Triclosan reckitt brand	HMDB
PHisoHex	HMDB

Molecular Formula

C₁₂H₇Cl₃O₂

Average Mass

289.542

Monoisotopic Mass

287.951162589

IUPAC Name

5-chloro-2-(2,4-dichlorophenoxy)phenol

Traditional Name

triclosan

CAS Registry Number

Not Available

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 Key

XEFQLINVKFYRCS-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Diphenylethers

Direct Parent

Diphenylethers

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

aromatic ether (CHEBI:164200 )
phenols (CHEBI:164200 )
dichlorobenzene (CHEBI:164200 )
monochlorobenzenes (CHEBI:164200 )
a small molecule (CPD0-1227 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	5.53	ALOGPS
logP	4.98	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.69 m³·mol⁻¹	ChemAxon
Polarizability	25.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Breast Milk
Saliva
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192010	Sulfotransferase 1A1	Enzyme	P50225	Homo sapiens
MMDBp0192014	Estrogen sulfotransferase	Enzyme	P49888	Homo sapiens
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Actinobacteria	1	Human	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
General Exposome	U.S. Environmental Protection Agency	CompTox
Drugs	U.S. Environmental Protection Agency	CompTox
Drugs - Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox
Water	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Breast milk	Detected and Quantified	0.0000656				uM	Adult (>18 years old)	Female	Normal	HMDB	17007908
Human Blood	Detected and Quantified	0.000249				uM	Adult (>18 years old)	Female	Normal	HMDB	17007908
Human Breast milk	Detected and Quantified	0.00187				uM	Adult (>18 years old)	Female	Normal	HMDB	17007908
Human Blood	Detected and Quantified	0.0553				uM	Adult (>18 years old)	Female	Normal	HMDB	17007908
Human Blood	Detected and Quantified	0.00173	0.00294			uM	Adult (>18 years old)	Both	N/A	HMDB	18193205
Human Blood	Detected and Quantified	0.0038	0.00415			uM	Adult (>18 years old)	Both	N/A	HMDB	18193205
Human Urine	Detected and Quantified	0.00387		0.00289	0.0052	umol/mmol creatinine	Children (1-13 years old)	Not Specified	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.00426		0.00324	0.00555	umol/mmol creatinine	Adolescent (13-18 years old)	Not Specified	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.00481		0.00414	0.00555	umol/mmol creatinine	Not Specified	Female	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.00485		0.00379	0.00621	umol/mmol creatinine	Elderly (>65 years old)	Not Specified	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.0052		0.00442	0.0061	umol/mmol creatinine	Not Specified	Male	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.00539		0.00485	0.00598	umol/mmol creatinine	Adult (>18 years old)	Not Specified	N/A	HMDB	18335095
Human Urine	Detected and Quantified	0.00554		0.00484	0.00640	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	17007908
Human Urine	Detected and Quantified	0.00554		0.00484	0.00640	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	18193205
Human Urine	Detected and Quantified	0.00554		0.00484	0.00640	umol/mmol creatinine	Children (1-13 years old)	Not Specified	Normal	HMDB	18335095
Human Urine	Detected and Quantified	0.00640		0.00535	0.00773	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	17007908
Human Urine	Detected and Quantified	0.00640		0.00535	0.00773	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	18193205
Human Urine	Detected and Quantified	0.00640		0.00535	0.00773	umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	HMDB	18335095
Human Urine	Detected and Quantified			0.2	0.31	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.14	0.22	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.13	0.22	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.17	0.26	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.11	0.18	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Urine	Detected and Quantified			0.11	0.17	umol/mmol creatinine	Not Specified	Both	Triclosan Exposure	HMDB	National Health and Nutrition Examination Survey (NHANES Survey) 2019
Human Saliva	Detected but not Quantified						Adult (>18 years old)	Not Specified	Normal	HMDB	12097436
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0061385

DrugBank ID

DB08604

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C12059

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triclosan

METLIN ID

Not Available

PubChem Compound

5564

PDB ID

Not Available

ChEBI ID

164200

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1074/jbc.274.16.11110. [PubMed:10196195 ]
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. doi: 10.1016/s0278-6915(99)00164-7. [PubMed:10722890 ]
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. doi: 10.1128/AAC.46.11.3343-3347.2002. [PubMed:12384334 ]
Russell AD: Whither triclosan? J Antimicrob Chemother. 2004 May;53(5):693-5. doi: 10.1093/jac/dkh171. Epub 2004 Apr 8. [PubMed:15073159 ]
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 ]
ON THE FATE OF TRICLOSAN IN HUMANS [Link]

Showing metabocard for 2,4,4'-trichloro-2'-hydroxydiphenylethe (MMDBc0012204)

MOL for #<Metabolite:0x00007f922100ca70>

3D MOL for #<Metabolite:0x00007f922100ca70>

3D SDF for #<Metabolite:0x00007f922100ca70>

3D-SDF for #<Metabolite:0x00007f922100ca70>

PDB for #<Metabolite:0x00007f922100ca70>

3D PDB for #<Metabolite:0x00007f922100ca70>

SMILES for #<Metabolite:0x00007f922100ca70>

INCHI for #<Metabolite:0x00007f922100ca70>

Structure for #<Metabolite:0x00007f922100ca70>

3D Structure for #<Metabolite:0x00007f922100ca70>