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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-12-19 19:52:52 UTC

Update Date

2020-04-22 23:33:44 UTC

HMDB ID

HMDB0061387

Secondary Accession Numbers

HMDB61387

Metabolite Identification

Common Name

Triclosan sulfate

Description

Triclosan sulfate 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

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


  Mrv0541 12191312542D          

 21 22  0  0  0  0            999 V2000
   -3.6241    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9096    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1952    1.1491    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4807   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662   -0.5009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518   -0.0884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0518    0.7366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7662    1.9741    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.6627   -0.5009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.6241    1.9741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0530   -0.5009    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.3386    2.3866    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0530    2.7991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9261    3.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7511    1.6722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  0  0  0  0
  8 10  2  0  0  0  0
  9 13  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
  9 14  1  0  0  0  0
 12 15  1  0  0  0  0
  1 16  1  0  0  0  0
  3 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  2  0  0  0  0
 18 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061387

> <DATABASE_NAME>
hmdb

> <SMILES>
OS(=O)(=O)OC1=C(OC2=CC=C(Cl)C=C2Cl)C=CC(Cl)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H7Cl3O5S/c13-7-1-3-10(9(15)5-7)19-11-4-2-8(14)6-12(11)20-21(16,17)18/h1-6H,(H,16,17,18)

> <INCHI_KEY>
ZPFYUMPBKRRSTR-UHFFFAOYSA-N

> <FORMULA>
C12H7Cl3O5S

> <MOLECULAR_WEIGHT>
369.605

> <EXACT_MASS>
367.907977145

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.229472945105016

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[5-chloro-2-(2,4-dichlorophenoxy)phenyl]oxidanesulfonic acid

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
4.50678836

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
-3.067684388095169

> <JCHEM_PKA_STRONGEST_BASIC>
-9.314915660333384

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
78.68589999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.18e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[5-chloro-2-(2,4-dichlorophenoxy)phenyl]oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-DEC-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-DEC-13         0                                  
HETATM    1  C   UNK     0      -6.765   2.145   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.099   1.375   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.099  -0.165   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.765  -0.935   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.431  -0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.431   1.375   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.098   2.145   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.764   1.375   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.430   2.145   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.764  -0.165   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.430  -0.935   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.097  -0.165   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.097   1.375   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -1.430   3.685   0.000  0.00  0.00          Cl+0
HETATM   15 Cl   UNK     0       1.237  -0.935   0.000  0.00  0.00          Cl+0
HETATM   16  O   UNK     0      -6.765   3.685   0.000  0.00  0.00           O+0
HETATM   17 Cl   UNK     0      -9.432  -0.935   0.000  0.00  0.00          Cl+0
HETATM   18  S   UNK     0      -8.099   4.455   0.000  0.00  0.00           S+0
HETATM   19  O   UNK     0      -9.432   5.225   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -7.329   5.789   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -8.869   3.121   0.000  0.00  0.00           O+0
CONECT    1    2    6   16                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8   13   14                                                  
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13    9   12                                                       
CONECT   14    9                                                            
CONECT   15   12                                                            
CONECT   16    1   18                                                       
CONECT   17    3                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0061387
HETATM    1  O1  UNL     1       1.784  -3.347  -0.819  1.00  0.00           O  
HETATM    2  S1  UNL     1       2.806  -2.246  -0.775  1.00  0.00           S  
HETATM    3  O2  UNL     1       2.873  -1.511  -2.073  1.00  0.00           O  
HETATM    4  O3  UNL     1       4.298  -2.913  -0.432  1.00  0.00           O  
HETATM    5  O4  UNL     1       2.424  -1.158   0.487  1.00  0.00           O  
HETATM    6  C1  UNL     1       1.967   0.143   0.200  1.00  0.00           C  
HETATM    7  C2  UNL     1       2.879   1.164   0.062  1.00  0.00           C  
HETATM    8  C3  UNL     1       2.441   2.435  -0.218  1.00  0.00           C  
HETATM    9 CL1  UNL     1       3.649   3.711  -0.385  1.00  0.00          CL  
HETATM   10  C4  UNL     1       1.101   2.714  -0.365  1.00  0.00           C  
HETATM   11  C5  UNL     1       0.203   1.663  -0.221  1.00  0.00           C  
HETATM   12  C6  UNL     1       0.609   0.387   0.058  1.00  0.00           C  
HETATM   13  O5  UNL     1      -0.227  -0.693   0.216  1.00  0.00           O  
HETATM   14  C7  UNL     1      -1.595  -0.564   0.153  1.00  0.00           C  
HETATM   15  C8  UNL     1      -2.291  -1.224  -0.863  1.00  0.00           C  
HETATM   16  C9  UNL     1      -3.660  -1.143  -0.989  1.00  0.00           C  
HETATM   17  C10 UNL     1      -4.349  -0.378  -0.068  1.00  0.00           C  
HETATM   18 CL2  UNL     1      -6.089  -0.290  -0.250  1.00  0.00          CL  
HETATM   19  C11 UNL     1      -3.681   0.282   0.943  1.00  0.00           C  
HETATM   20  C12 UNL     1      -2.306   0.199   1.068  1.00  0.00           C  
HETATM   21 CL3  UNL     1      -1.471   1.031   2.391  1.00  0.00          CL  
HETATM   22  H1  UNL     1       4.870  -2.198  -0.022  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.952   0.938   0.180  1.00  0.00           H  
HETATM   24  H3  UNL     1       0.772   3.724  -0.586  1.00  0.00           H  
HETATM   25  H4  UNL     1      -0.861   1.877  -0.349  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.698  -1.818  -1.569  1.00  0.00           H  
HETATM   27  H6  UNL     1      -4.162  -1.670  -1.792  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.238   0.885   1.666  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    4   22
CONECT    5    6
CONECT    6    7    7   12
CONECT    7    8   23
CONECT    8    9   10   10
CONECT   10   11   24
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14
CONECT   14   15   15   20
CONECT   15   16   26
CONECT   16   17   17   27
CONECT   17   18   19
CONECT   19   20   20   28
CONECT   20   21
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Triclosan sulfuric acid	Generator
Triclosan sulphate	Generator
Triclosan sulphuric acid	Generator

Chemical Formula

C₁₂H₇Cl₃O₅S

Average Molecular Weight

369.605

Monoisotopic Molecular Weight

367.907977145

IUPAC Name

[5-chloro-2-(2,4-dichlorophenoxy)phenyl]oxidanesulfonic acid

Traditional Name

[5-chloro-2-(2,4-dichlorophenoxy)phenyl]oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

OS(=O)(=O)OC1=C(OC2=CC=C(Cl)C=C2Cl)C=CC(Cl)=C1

InChI Identifier

InChI=1S/C12H7Cl3O5S/c13-7-1-3-10(9(15)5-7)19-11-4-2-8(14)6-12(11)20-21(16,17)18/h1-6H,(H,16,17,18)

InChI Key

ZPFYUMPBKRRSTR-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
Phenylsulfate
Arylsulfate
Phenoxy compound
1,3-dichlorobenzene
Phenol ether
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Sulfuric acid ester
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Ether
Organohalogen compound
Hydrocarbon derivative
Organochloride
Organooxygen compound
Organic oxygen compound
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 22173800)

Tissue

Epithelium

Epidermis (HMDB: HMDB0061387)

Source

Endogenous

Endogenous (HMDB: HMDB0061387)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0092 g/L	ALOGPS
logP	1.96	ALOGPS
logP	4.51	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	-3.1	ChemAxon
pKa (Strongest Basic)	-9.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.69 m³·mol⁻¹	ChemAxon
Polarizability	31.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	169.053	30932474
DeepCCS	[M-H]-	166.695	30932474
DeepCCS	[M-2H]-	199.774	30932474
DeepCCS	[M+Na]+	175.146	30932474
AllCCS	[M+H]+	169.8	32859911
AllCCS	[M+H-H2O]+	166.8	32859911
AllCCS	[M+NH4]+	172.6	32859911
AllCCS	[M+Na]+	173.3	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	152.3	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.44 minutes	32390414
Predicted by Siyang on May 30, 2022	18.4396 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2393.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	631.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	225.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	436.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	805.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	880.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	343.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1604.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	681.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1710.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	470.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	610.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	294.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	40.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Triclosan sulfate	OS(=O)(=O)OC1=C(OC2=CC=C(Cl)C=C2Cl)C=CC(Cl)=C1	3840.0	Standard polar	33892256
Triclosan sulfate	OS(=O)(=O)OC1=C(OC2=CC=C(Cl)C=C2Cl)C=CC(Cl)=C1	2457.1	Standard non polar	33892256
Triclosan sulfate	OS(=O)(=O)OC1=C(OC2=CC=C(Cl)C=C2Cl)C=CC(Cl)=C1	2616.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Triclosan sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	2571.0	Semi standard non polar	33892256
Triclosan sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	2708.9	Standard non polar	33892256
Triclosan sulfate,1TMS,isomer #1	C[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	3790.2	Standard polar	33892256
Triclosan sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	2864.8	Semi standard non polar	33892256
Triclosan sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	2972.8	Standard non polar	33892256
Triclosan sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OS(=O)(=O)OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl	3761.6	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Epidermis

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	N/A	22173800	details

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

67606152

PDB ID

Not Available

ChEBI ID

89301

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Triclosan sulfate (HMDB0061387)

MOL for HMDB0061387 (Triclosan sulfate)

3D MOL for HMDB0061387 (Triclosan sulfate)

3D SDF for HMDB0061387 (Triclosan sulfate)

3D-SDF for HMDB0061387 (Triclosan sulfate)

PDB for HMDB0061387 (Triclosan sulfate)

3D PDB for HMDB0061387 (Triclosan sulfate)

SMILES for HMDB0061387 (Triclosan sulfate)

INCHI for HMDB0061387 (Triclosan sulfate)

Structure for HMDB0061387 (Triclosan sulfate)

3D Structure for HMDB0061387 (Triclosan sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized