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Showing NP-Card for Methyl phenyl sulfide (NP0047972)

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Record Information
Version2.0
Created at2022-03-17 20:48:56 UTC
Updated at2022-03-17 20:48:56 UTC
NP-MRD IDNP0047972
Secondary Accession NumbersNone
Natural Product Identification
Common NameMethyl phenyl sulfide
DescriptionMethyl phenyl sulfide, also known as (methylthio)benzene or (1-thiaethyl)benzene, belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group. Methyl phenyl sulfide is possibly neutral. Methyl phenyl sulfide is a solvent, spicy, and toluene tasting compound. Outside of the human body, Methyl phenyl sulfide has been detected, but not quantified in, a few different foods, such as cereals and cereal products, coffee and coffee products, and herbs and spices. Methyl phenyl sulfide was first documented in 2001 (PMID: 11121113). This could make methyl phenyl sulfide a potential biomarker for the consumption of these foods (PMID: 21168267) (PMID: 21261073) (PMID: 23053095) (PMID: 24092008).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047972 (Methyl phenyl sulfide)


  Mrv0541 05061307492D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    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
    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
M  END
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3D MOL for NP0047972 (Methyl phenyl sulfide)

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3D SDF for NP0047972 (Methyl phenyl sulfide)

  Mrv0541 05061307492D          

  8  8  0  0  0  0            999 V2000
    0.0000    2.4750    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
    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3

> <INCHI_KEY>
HNKJADCVZUBCPG-UHFFFAOYSA-N

> <FORMULA>
C7H8S

> <MOLECULAR_WEIGHT>
124.203

> <EXACT_MASS>
124.034670946

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
13.906557275084708

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(methylsulfanyl)benzene

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.6014629543333334

> <ALOGPS_LOGS>
-2.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
38.8169

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.84e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
thioanisole

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0047972 (Methyl phenyl sulfide)
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PDB for NP0047972 (Methyl phenyl sulfide)
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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   0.000   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  S   UNK     0       1.334   3.850   0.000  0.00  0.00           S+0
CONECT    1    8                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    7                                                       
CONECT    7    5    6    8                                                  
CONECT    8    1    7                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END

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3D PDB for NP0047972 (Methyl phenyl sulfide)
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SMILES for NP0047972 (Methyl phenyl sulfide)
CSC1=CC=CC=C1
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INCHI for NP0047972 (Methyl phenyl sulfide)
InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
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View in JSmol
Synonyms
ValueSource
(1-Thiaethyl)benzeneChEBI
(Methylthio)benzeneChEBI
1-Phenyl-1-thiaethaneChEBI
Methyl phenyl thioetherChEBI
MethylphenylsulfideChEBI
MethylthiobenzeneChEBI
Phenyl methyl sulfideChEBI
PhenylthiomethaneChEBI
MethylphenylsulphideGenerator
Phenyl methyl sulphideGenerator
Methyl phenyl sulphideGenerator
Methylsulfanyl-benzeneHMDB
Methylsulphanyl-benzeneHMDB
(Methylsulfanyl)benzeneHMDB
(Methylthio)-benzeneHMDB
(Methylthio)benzene, 9ciHMDB
FEMA 3873HMDB
Methyl phenylsulfideHMDB
MethylmercaptobenzeneHMDB
Sulfide, methyl phenylHMDB
Sulfide, methyl phenyl (6ci,8ci)HMDB
Thio-anisoleHMDB
ThioanisolHMDB
ThioanisoleHMDB
Methyl phenyl sulfideMeSH
Chemical FormulaC7H8S
Average Mass124.2030 Da
Monoisotopic Mass124.03467 Da
IUPAC Name(methylsulfanyl)benzene
Traditional Namethioanisole
CAS Registry Number100-68-5
SMILES
CSC1=CC=CC=C1
InChI Identifier
InChI=1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3
InChI KeyHNKJADCVZUBCPG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aryl thioethers. These are organosulfur compounds containing a thioether group that is substituted by an aryl group.
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassThioethers  
Sub ClassAryl thioethers  
Direct ParentAryl thioethers  
Alternative Parents
Substituents
  • Aryl thioether
    • 

  • Thiophenol ether
    • 

  • Alkylarylthioether
    • 

  • Benzenoid
    • 

  • Monocyclic benzene moiety
    • 

  • Sulfenyl compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP2.86ALOGPS
logP2.6ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.82 m³·mol⁻¹ChemAxon
Polarizability13.91 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034448  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012855  
KNApSAcK IDNot Available
Chemspider ID7239  
KEGG Compound IDNot Available
BioCyc IDCPD-14757  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7520  
PDB ID16R  
ChEBI ID134281  
Good Scents IDNot Available
References
General References
  1. ten Brink HB, Schoemaker HE, Wever R: Sulfoxidation mechanism of vanadium bromoperoxidase from Ascophyllum nodosum. Evidence for direct oxygen transfer catalysis. Eur J Biochem. 2001 Jan;268(1):132-8. doi: 10.1046/j.1432-1327.2001.01856.x. [PubMed:11121113  ] 
  2. Wan S, Li G, An T, Guo B: Co-treatment of single, binary and ternary mixture gas of ethanethiol, dimethyl disulfide and thioanisole in a biotrickling filter seeded with Lysinibacillus sphaericus RG-1. J Hazard Mater. 2011 Feb 28;186(2-3):1050-7. doi: 10.1016/j.jhazmat.2010.11.099.  Epub 2010 Nov 30. [PubMed:21168267  ] 
  3. El'kin AA, Grishko VV, Ivshina IB: [Oxidative biotransformation of thioanisole by Rhodococcus rhodochrous IEGM 66 cells]. Prikl Biokhim Mikrobiol. 2010 Nov-Dec;46(6):637-43. [PubMed:21261073  ] 
  4. Ramadhan SH, Matsui T, Nakano K, Minami H: High cell density cultivation of Pseudomonas putida strain HKT554 and its application for optically active sulfoxide production. Appl Microbiol Biotechnol. 2013 Mar;97(5):1903-7. doi: 10.1007/s00253-012-4445-x. Epub 2012 Sep 29. [PubMed:23053095  ] 
  5. He YC, Ma CL, Yang ZX, Zhou M, Xing Z, Ma JT, Yu HL: Highly enantioselective oxidation of phenyl methyl sulfide and its derivatives into optically pure (S)-sulfoxides with Rhodococcus sp. CCZU10-1 in an n-octane-water biphasic system. Appl Microbiol Biotechnol. 2013 Dec;97(24):10329-37. doi: 10.1007/s00253-013-5258-2. Epub 2013 Oct 5. [PubMed:24092008  ]