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Showing NP-Card for Benzenethiol (NP0336914)

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Record Information
Version2.0
Created at2024-09-11 08:24:31 UTC
Updated at2024-09-11 08:24:32 UTC
NP-MRD IDNP0336914
Secondary Accession NumbersNone
Natural Product Identification
Common NameBenzenethiol
DescriptionBenzenethiol, also known as mercaptobenzene or phenyl mercaptan, 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. Benzenethiol is a very weakly acidic compound (based on its pKa). Benzenethiol is a garlic, penetrating, and repulsive tasting compound. Outside of the human body,. Benzenethiol is a flavouring agent Benzenethiol is a chemical compound with the formula C6H5SH, and sometimes abbreviated as PhSH. The prefix thio- implies a sulfur-containing compound and when used before a root word name for a compound which would normally contain an oxygen atom, thio- commonly means that the oxygen atom is replaced by a sulfur atom. Benzenethiol was first documented in 2008 (PMID: 18266323). The organosulfur ligand in medicine merthiolate is a thiophenol (PMID: 23902004) (PMID: 23961762) (PMID: 18321603) (PMID: 22121689).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0336914 (Benzenethiol)


  Mrv0541 05061307202D          

  7  7  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
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3D MOL for NP0336914 (Benzenethiol)

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3D SDF for NP0336914 (Benzenethiol)

  Mrv0541 05061307202D          

  7  7  0  0  0  0            999 V2000
    0.7145   -0.4125    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336914

> <DATABASE_NAME>
NP-MRD

> <SMILES>
SC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H

> <INCHI_KEY>
RMVRSNDYEFQCLF-UHFFFAOYSA-N

> <FORMULA>
C6H6S

> <MOLECULAR_WEIGHT>
110.177

> <EXACT_MASS>
110.019020882

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
11.926537929815595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzenethiol

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.0664529956666664

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.638428954887124

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
34.0678

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thiophenol

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0336914 (Benzenethiol)
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PDB for NP0336914 (Benzenethiol)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   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
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   14    0
END

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3D PDB for NP0336914 (Benzenethiol)
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SMILES for NP0336914 (Benzenethiol)
SC1=CC=CC=C1
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INCHI for NP0336914 (Benzenethiol)
InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
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View in JSmol
Synonyms
ValueSource
MercaptobenzeneChEBI
Phenyl mercaptanChEBI
PhenylthiolChEBI
FEMA 3616HMDB
Mercapto-benzeneHMDB
PhenylmercaptanHMDB
Sodium benzenethiolateHMDB
Thio-phenolHMDB
ThiofenolHMDB
ThiophenateHMDB
ThiophenolHMDB
Thiophenol, potassium saltHMDB
Thiophenol, sodium saltHMDB
Thiophenol, copper (+1) saltHMDB
BenzenethiolMeSH
Chemical FormulaC6H6S
Average Mass110.1770 Da
Monoisotopic Mass110.01902 Da
IUPAC Namebenzenethiol
Traditional Namethiophenol
CAS Registry NumberNot Available
SMILES
SC1=CC=CC=C1
InChI Identifier
InChI=1S/C6H6S/c7-6-4-2-1-3-5-6/h1-5,7H
InChI KeyRMVRSNDYEFQCLF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Monocyclic benzene moiety
    • 

  • Arylthiol
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
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
logP2.26ALOGPS
logP2.07ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)6.64ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity34.07 m³·mol⁻¹ChemAxon
Polarizability11.93 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033746  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011878  
KNApSAcK IDNot Available
Chemspider ID7681  
KEGG Compound IDNot Available
BioCyc IDCPD-8132  
BiGG IDNot Available
Wikipedia LinkThiophenol  
METLIN IDNot Available
PubChem Compound7969  
PDB IDBT6  
ChEBI ID48498  
Good Scents IDNot Available
References
General References
  1. Kitaguchi Y, Habuka S, Mitsui T, Okuyama H, Hatta S, Aruga T: Comparative study of phenol and thiophenol adsorption on Cu(110). J Chem Phys. 2013 Jul 28;139(4):044708. doi: 10.1063/1.4815968. [PubMed:23902004  ] 
  2. Cabalo J, Guicheteau JA, Christesen S: Toward understanding the influence of intermolecular interactions and molecular orientation on the chemical enhancement of SERS. J Phys Chem A. 2013 Sep 19;117(37):9028-38. doi: 10.1021/jp403458k. Epub 2013 Sep  5. [PubMed:23961762  ] 
  3. Barrese AA 3rd, Genis C, Fisher SZ, Orwenyo JN, Kumara MT, Dutta SK, Phillips E, Kiddle JJ, Tu C, Silverman DN, Govindasamy L, Agbandje-McKenna M, McKenna R, Tripp BC: Inhibition of carbonic anhydrase II by thioxolone: a mechanistic and structural study. Biochemistry. 2008 Mar 11;47(10):3174-84. doi: 10.1021/bi702385k. Epub 2008 Feb  12. [PubMed:18266323  ] 
  4. Patil G, Rudolph R, Lange C: In vitro-refolding of a single-chain Fv fragment in the presence of heteroaromatic thiols. J Biotechnol. 2008 Apr 30;134(3-4):218-21. doi: 10.1016/j.jbiotec.2008.01.009.  Epub 2008 Jan 18. [PubMed:18321603  ] 
  5. Park G, Lee KG, Lee SJ, Park TJ, Wi R, Wang KW, Kim DH: Ultrasound-aided formation of gold nanoparticles on multi-walled carbon nanotubes functionalized with mercaptobenzene moieties. J Nanosci Nanotechnol. 2011 Jul;11(7):6222-6. doi: 10.1166/jnn.2011.4445. [PubMed:22121689  ]