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Showing metabocard for 4-Chlorothiophenol (HMDB0246403)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-10 23:25:32 UTC
Update Date2021-09-26 22:55:28 UTC
HMDB IDHMDB0246403
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Chlorothiophenol
Description4-Chlorothiophenol belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom. Based on a literature review a significant number of articles have been published on 4-Chlorothiophenol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 4-chlorothiophenol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 4-Chlorothiophenol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0246403 (4-Chlorothiophenol)


  Mrv1652309112101252D          

  8  8  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0246403 (4-Chlorothiophenol)

HMDB0246403
     RDKit          3D
4-Chlorothiophenol
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.8418    0.3316   -0.4824 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0808    0.1221   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -1.1312   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -1.2568   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -0.1261    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -0.3823    0.3450 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0775    1.1188    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    1.2396   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788    0.0929    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -1.9892   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239   -2.2640    0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.9924    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    2.2522   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

3D SDF for HMDB0246403 (4-Chlorothiophenol)


  Mrv1652309112101252D          

  8  8  0  0  0  0            999 V2000
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  3  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246403

> <DATABASE_NAME>
hmdb

> <SMILES>
SC1=CC=C(Cl)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H5ClS/c7-5-1-3-6(8)4-2-5/h1-4,8H

> <INCHI_KEY>
VZXOZSQDJJNBRC-UHFFFAOYSA-N

> <FORMULA>
C6H5ClS

> <MOLECULAR_WEIGHT>
144.62

> <EXACT_MASS>
143.980049

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
14.214382610479689

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-chlorobenzene-1-thiol

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
2.6704976719999998

> <ALOGPS_LOGS>
-2.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.464777545620553

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
38.8726

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-chlorobenzenethiol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0246403 (4-Chlorothiophenol)

HMDB0246403
     RDKit          3D
4-Chlorothiophenol
 13 13  0  0  0  0  0  0  0  0999 V2000
    2.8418    0.3316   -0.4824 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0808    0.1221   -0.2479 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4935   -1.1312   -0.2051 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -1.2568   -0.0213 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6525   -0.1261    0.1184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3657   -0.3823    0.3450 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.0775    1.1188    0.0771 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815    1.2396   -0.1051 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4788    0.0929    0.7720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1320   -1.9892   -0.3181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3239   -2.2640    0.0095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7327    1.9924    0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7218    2.2522   -0.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  2  1  0
  1  9  1  0
  3 10  1  0
  4 11  1  0
  7 12  1  0
  8 13  1  0
M  END
Download

PDB for HMDB0246403 (4-Chlorothiophenol)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
HETATM    8 Cl   UNK     0       1.334  -2.310   0.000  0.00  0.00          Cl+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    3                                                            
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0246403 (4-Chlorothiophenol)

COMPND    HMDB0246403
HETATM    1  S1  UNL     1       2.842   0.332  -0.482  1.00  0.00           S  
HETATM    2  C1  UNL     1       1.081   0.122  -0.248  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.494  -1.131  -0.205  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.878  -1.257  -0.021  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.653  -0.126   0.118  1.00  0.00           C  
HETATM    6 CL1  UNL     1      -3.366  -0.382   0.345  1.00  0.00          CL  
HETATM    7  C5  UNL     1      -1.078   1.119   0.077  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.282   1.240  -0.105  1.00  0.00           C  
HETATM    9  H1  UNL     1       3.479   0.093   0.772  1.00  0.00           H  
HETATM   10  H2  UNL     1       1.132  -1.989  -0.318  1.00  0.00           H  
HETATM   11  H3  UNL     1      -1.324  -2.264   0.010  1.00  0.00           H  
HETATM   12  H4  UNL     1      -1.733   1.992   0.193  1.00  0.00           H  
HETATM   13  H5  UNL     1       0.722   2.252  -0.135  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3    3    8
CONECT    3    4   10
CONECT    4    5    5   11
CONECT    5    6    7
CONECT    7    8    8   12
CONECT    8   13
END
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SMILES for HMDB0246403 (4-Chlorothiophenol)

SC1=CC=C(Cl)C=C1
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INCHI for HMDB0246403 (4-Chlorothiophenol)

InChI=1S/C6H5ClS/c7-5-1-3-6(8)4-2-5/h1-4,8H
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC6H5ClS
Average Molecular Weight144.62
Monoisotopic Molecular Weight143.980049
IUPAC Name4-chlorobenzene-1-thiol
Traditional Name4-chlorobenzenethiol
CAS Registry NumberNot Available
SMILES
SC1=CC=C(Cl)C=C1
InChI Identifier
InChI=1S/C6H5ClS/c7-5-1-3-6(8)4-2-5/h1-4,8H
InChI KeyVZXOZSQDJJNBRC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as thiophenols. Thiophenols are compounds containing a thiophenol ring, which a phenol derivative obtained by replacing the oxygen atom from the hydroxyl group (attached to the benzene) by a sulfur atom.
KingdomOrganic compounds
Super ClassBenzenoids
ClassThiophenols
Sub ClassNot Available
Direct ParentThiophenols
Alternative Parents
Substituents
  • Thiophenol
  • Halobenzene
  • Chlorobenzene
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Arylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.99ALOGPS
logP2.67ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)5.46ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity38.87 m³·mol⁻¹ChemAxon
Polarizability14.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+125.86830932474
DeepCCS[M-H]-122.37630932474
DeepCCS[M-2H]-159.28130932474
DeepCCS[M+Na]+134.46830932474
AllCCS[M+H]+125.532859911
AllCCS[M+H-H2O]+120.732859911
AllCCS[M+NH4]+129.932859911
AllCCS[M+Na]+131.232859911
AllCCS[M-H]-119.432859911
AllCCS[M+Na-2H]-121.832859911
AllCCS[M+HCOO]-124.632859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.9372 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.54 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1844.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid554.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid215.8 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid393.0 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid305.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid542.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid577.5 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)409.9 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1135.2 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid459.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1198.9 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid410.1 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid401.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate589.8 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA339.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water125.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-ChlorothiophenolSC1=CC=C(Cl)C=C11706.9Standard polar33892256
4-ChlorothiophenolSC1=CC=C(Cl)C=C11145.4Standard non polar33892256
4-ChlorothiophenolSC1=CC=C(Cl)C=C11151.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Chlorothiophenol,1TMS,isomer #1C[Si](C)(C)SC1=CC=C(Cl)C=C11384.3Semi standard non polar33892256
4-Chlorothiophenol,1TMS,isomer #1C[Si](C)(C)SC1=CC=C(Cl)C=C11361.7Standard non polar33892256
4-Chlorothiophenol,1TMS,isomer #1C[Si](C)(C)SC1=CC=C(Cl)C=C11549.5Standard polar33892256
4-Chlorothiophenol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)SC1=CC=C(Cl)C=C11622.9Semi standard non polar33892256
4-Chlorothiophenol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)SC1=CC=C(Cl)C=C11603.2Standard non polar33892256
4-Chlorothiophenol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)SC1=CC=C(Cl)C=C11723.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Chlorothiophenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0007-9700000000-6ff9c50abb058e04d7d22021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Chlorothiophenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 10V, Positive-QTOFsplash10-0006-0900000000-1f3529d89363ed76006c2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 20V, Positive-QTOFsplash10-0006-2900000000-f4f16539056daa61022e2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 40V, Positive-QTOFsplash10-0006-3900000000-caf9187a812cd5b7e8712021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 10V, Negative-QTOFsplash10-0006-0900000000-3ea47ec8cb4ee6e6d1462021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 20V, Negative-QTOFsplash10-0006-0900000000-3ea47ec8cb4ee6e6d1462021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Chlorothiophenol 40V, Negative-QTOFsplash10-0a4i-9200000000-dbabb44a00fe310cd9452021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7527
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7815
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]