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Showing metabocard for Phenylmethanethiol (HMDB0029633)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:40 UTC
Update Date2023-02-21 17:18:53 UTC
HMDB IDHMDB0029633
Secondary Accession Numbers
  • HMDB29633
Metabolite Identification
Common NamePhenylmethanethiol
DescriptionPhenylmethanethiol, also known as alpha-mercaptotoluene or alpha-toluenethiol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Phenylmethanethiol is an alliaceous, coffee, and garlic tasting compound. Phenylmethanethiol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Phenylmethanethiol.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0029633 (Phenylmethanethiol)

  Mrv0541 02241216292D          

  8  8  0  0  0  0            999 V2000
    1.0727    1.2383    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
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3D MOL for HMDB0029633 (Phenylmethanethiol)

HMDB0029633
     RDKit          3D
Phenylmethanethiol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.9919    0.3888    0.7081 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260    0.6647   -0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530    0.2253   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -1.0585   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2901   -1.4142   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -0.4975    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    0.7775    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    1.1580    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.8090    1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1216    0.1154   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8635    1.7487   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -1.7845   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -2.4161   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -0.7748    0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.5054    1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    2.1707    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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3D SDF for HMDB0029633 (Phenylmethanethiol)

  Mrv0541 02241216292D          

  8  8  0  0  0  0            999 V2000
    1.0727    1.2383    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0727    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3295   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295   -1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3295    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029633

> <DATABASE_NAME>
hmdb

> <SMILES>
SCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2

> <INCHI_KEY>
UENWRTRMUIOCKN-UHFFFAOYSA-N

> <FORMULA>
C7H8S

> <MOLECULAR_WEIGHT>
124.203

> <EXACT_MASS>
124.034670946

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
13.785797934410102

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
phenylmethanethiol

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.4572654446666666

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.93118052784932

> <JCHEM_PKA_STRONGEST_BASIC>
-9.721234435270564

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
38.9025

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.50e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl mercaptan

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0029633 (Phenylmethanethiol)

HMDB0029633
     RDKit          3D
Phenylmethanethiol
 16 16  0  0  0  0  0  0  0  0999 V2000
    2.9919    0.3888    0.7081 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.8260    0.6647   -0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4530    0.2253   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0118   -1.0585   -0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2901   -1.4142   -0.1988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1376   -0.4975    0.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6654    0.7775    0.6184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3745    1.1580    0.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6833   -0.8090    1.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1216    0.1154   -1.5681 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8635    1.7487   -0.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6649   -1.7845   -1.0091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6565   -2.4161   -0.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463   -0.7748    0.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.5054    1.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0210    2.1707    0.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  3  1  0
  1  9  1  0
  2 10  1  0
  2 11  1  0
  4 12  1  0
  5 13  1  0
  6 14  1  0
  7 15  1  0
  8 16  1  0
M  END
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PDB for HMDB0029633 (Phenylmethanethiol)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0       2.002   2.311   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0       2.002   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.615  -0.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.615  -1.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.615  -2.311   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.002  -1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.002  -0.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.615   0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0029633 (Phenylmethanethiol)

COMPND    HMDB0029633
HETATM    1  S1  UNL     1       2.992   0.389   0.708  1.00  0.00           S  
HETATM    2  C1  UNL     1       1.826   0.665  -0.658  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.453   0.225  -0.307  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.012  -1.058  -0.551  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.290  -1.414  -0.199  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.138  -0.497   0.388  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.665   0.777   0.618  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.374   1.158   0.278  1.00  0.00           C  
HETATM    9  H1  UNL     1       2.683  -0.809   1.366  1.00  0.00           H  
HETATM   10  H2  UNL     1       2.122   0.115  -1.568  1.00  0.00           H  
HETATM   11  H3  UNL     1       1.864   1.749  -0.896  1.00  0.00           H  
HETATM   12  H4  UNL     1       0.665  -1.784  -1.009  1.00  0.00           H  
HETATM   13  H5  UNL     1      -1.656  -2.416  -0.381  1.00  0.00           H  
HETATM   14  H6  UNL     1      -3.146  -0.775   0.660  1.00  0.00           H  
HETATM   15  H7  UNL     1      -2.325   1.505   1.080  1.00  0.00           H  
HETATM   16  H8  UNL     1      -0.021   2.171   0.469  1.00  0.00           H  
CONECT    1    2    9
CONECT    2    3   10   11
CONECT    3    4    4    8
CONECT    4    5   12
CONECT    5    6    6   13
CONECT    6    7   14
CONECT    7    8    8   15
CONECT    8   16
END
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SMILES for HMDB0029633 (Phenylmethanethiol)

SCC1=CC=CC=C1
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INCHI for HMDB0029633 (Phenylmethanethiol)

InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC7H8S
Average Molecular Weight124.203
Monoisotopic Molecular Weight124.034670946
IUPAC Namephenylmethanethiol
Traditional Namebenzyl mercaptan
CAS Registry Number100-53-8
SMILES
SCC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8S/c8-6-7-4-2-1-3-5-7/h1-5,8H,6H2
InChI KeyUENWRTRMUIOCKN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • Alkylthiol
  • Hydrocarbon derivative
  • Organosulfur compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-30 °CNot Available
Boiling Point194.00 to 195.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility732.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.739 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000803
KNApSAcK IDNot Available
Chemspider ID13851383
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl mercaptan
METLIN IDNot Available
PubChem Compound7509
PDB IDNot Available
ChEBI ID137674
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1017561
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Henderson AP, Bleasdale C, Delaney K, Lindstrom AB, Rappaport SM, Waidyanatha S, Watson WP, Golding BT: Evidence for the formation of Michael adducts from reactions of (E,E)-muconaldehyde with glutathione and other thiols. Bioorg Chem. 2005 Oct;33(5):363-73. Epub 2005 Jul 11. [PubMed:16005934 ]
  2. Muglali MI, Liu J, Bashir A, Borissov D, Xu M, Wang Y, Woll C, Rohwerder M: On the complexation kinetics for metallization of organic layers: palladium onto a pyridine-terminated araliphatic thiol film. Phys Chem Chem Phys. 2012 Apr 14;14(14):4703-12. doi: 10.1039/c2cp40072c. Epub 2012 Feb 29. [PubMed:22377589 ]
  3. Wood WF, Sollers BG, Dragoo GA, Dragoo JW: Volatile components in defensive spray of the hooded skunk, Mephitis macroura. J Chem Ecol. 2002 Sep;28(9):1865-70. [PubMed:12449512 ]
  4. Labarbe B, Cheynier V, Brossaud F, Souquet JM, Moutounet M: Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J Agric Food Chem. 1999 Jul;47(7):2719-23. [PubMed:10552552 ]
  5. Pelyvas I, Hasegawa A, Whistler RL: Synthesis of N-trifluoroacetyl-L-acosamine, N-trifluoroacetyl-L-daunosamine, and their 1-thio analogs. Carbohydr Res. 1986 Feb 1;146(2):193-203. [PubMed:3955573 ]
  6. Hasegawa JY, Hamada M, Miyamoto T, Nishide K, Kajimoto T, Uenishi J, Node M: The application of phenylmethanethiol and benzenethiol derivatives as odorless organosulfur reagents in the synthesis of thiosugars and thioglycosides. Carbohydr Res. 2005 Oct 31;340(15):2360-8. [PubMed:16143318 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .