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Showing metabocard for 1-Isothiocyanato-2-phenylethane (HMDB0038445)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:45:46 UTC
Update Date2023-02-21 17:26:36 UTC
HMDB IDHMDB0038445
Secondary Accession Numbers
  • HMDB38445
Metabolite Identification
Common Name1-Isothiocyanato-2-phenylethane
Description1-Isothiocyanato-2-phenylethane, also known as 2-phenylethyl isothiocyanate (PEITC) or (2-isothiocyanatoethyl) benzene is an isothiocyanate having a phenethyl group attached to the nitrogen. It is a naturally occurring compound found in some cruciferous vegetables (e.g. watercress) and is known to possess anticancer properties. It has a role as an antineoplastic agent, a metabolite and an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It 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. PEITC is found in high concentrations in kohlrabis. In terms of biosynthesis, PEITC is produced from gluconasturtiin by the action of the enzyme myrosinase. PEITC has been used in trials studying the prevention and treatment of leukemia, lung cancer, tobacco use disorder, and lymphoproliferative disorders.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

  Mrv1652305261923512D          

 11 11  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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    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
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
Download

3D MOL for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

HMDB0038445
     RDKit          3D
1-Isothiocyanato-2-phenylethane
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.8061    1.0117   -0.3638 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3346    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -1.2555    0.1554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -0.9498    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871   -0.3426   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    0.0243   -0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -0.9101   -0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258   -0.5691   -0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687    0.7039   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    1.6386    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6721    1.2839   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347   -1.8953    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7637   -0.2698    1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -1.1153   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.5417   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1024   -1.9061   -1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006   -1.3032   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    0.9944    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2641    2.6209    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    2.0321    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
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3D SDF for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

  Mrv1652305261923512D          

 11 11  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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    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
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    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
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038445

> <DATABASE_NAME>
hmdb

> <SMILES>
S=C=NCCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2

> <INCHI_KEY>
IZJDOKYDEWTZSO-UHFFFAOYSA-N

> <FORMULA>
C9H9NS

> <MOLECULAR_WEIGHT>
163.239

> <EXACT_MASS>
163.045569983

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
18.10142290717055

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2-isothiocyanatoethyl)benzene

> <ALOGPS_LOGP>
3.41

> <JCHEM_LOGP>
3.082784376333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.144110058525007

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
50.6967

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenethyl isothiocyanate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

HMDB0038445
     RDKit          3D
1-Isothiocyanato-2-phenylethane
 20 20  0  0  0  0  0  0  0  0999 V2000
    4.8061    1.0117   -0.3638 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.9726   -0.3346    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1148   -1.2555    0.1554 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7271   -0.9498    0.5318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0871   -0.3426   -0.6956 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    0.0243   -0.4842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036   -0.9101   -0.7544 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258   -0.5691   -0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9687    0.7039   -0.0901 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9910    1.6386    0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6721    1.2839   -0.0214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2347   -1.8953    0.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7637   -0.2698    1.3866 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1412   -1.1153   -1.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7009    0.5417   -0.9817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1024   -1.9061   -1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4006   -1.3032   -0.7692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0022    0.9944    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2641    2.6209    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1033    2.0321    0.1957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
  4 13  1  0
  5 14  1  0
  5 15  1  0
  7 16  1  0
  8 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
M  END
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PDB for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         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   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   11  S   UNK     0       5.335   7.700   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6    7    9                                                       
CONECT    7    6   10                                                       
CONECT    8   10   11                                                       
CONECT    9    4    5    6                                                  
CONECT   10    7    8                                                       
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

COMPND    HMDB0038445
HETATM    1  S1  UNL     1       4.806   1.012  -0.364  1.00  0.00           S  
HETATM    2  C1  UNL     1       3.973  -0.335   0.005  1.00  0.00           C  
HETATM    3  N1  UNL     1       3.115  -1.256   0.155  1.00  0.00           N  
HETATM    4  C2  UNL     1       1.727  -0.950   0.532  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.087  -0.343  -0.696  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.321   0.024  -0.484  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.304  -0.910  -0.754  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.626  -0.569  -0.557  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.969   0.704  -0.090  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.991   1.639   0.181  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.672   1.284  -0.021  1.00  0.00           C  
HETATM   12  H1  UNL     1       1.235  -1.895   0.832  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.764  -0.270   1.387  1.00  0.00           H  
HETATM   14  H3  UNL     1       1.141  -1.115  -1.494  1.00  0.00           H  
HETATM   15  H4  UNL     1       1.701   0.542  -0.982  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.102  -1.906  -1.116  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.401  -1.303  -0.769  1.00  0.00           H  
HETATM   18  H7  UNL     1      -4.002   0.994   0.073  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.264   2.621   0.541  1.00  0.00           H  
HETATM   20  H9  UNL     1       0.103   2.032   0.196  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3
CONECT    3    4
CONECT    4    5   12   13
CONECT    5    6   14   15
CONECT    6    7    7   11
CONECT    7    8   16
CONECT    8    9    9   17
CONECT    9   10   18
CONECT   10   11   11   19
CONECT   11   20
END
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SMILES for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

S=C=NCCC1=CC=CC=C1
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INCHI for HMDB0038445 (1-Isothiocyanato-2-phenylethane)

InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC9H9NS
Average Molecular Weight163.239
Monoisotopic Molecular Weight163.045569983
IUPAC Name(2-isothiocyanatoethyl)benzene
Traditional Namephenethyl isothiocyanate
CAS Registry Number2257-09-2
SMILES
S=C=NCCC1=CC=CC=C1
InChI Identifier
InChI=1S/C9H9NS/c11-8-10-7-6-9-4-2-1-3-5-9/h1-5H,6-7H2
InChI KeyIZJDOKYDEWTZSO-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
  • Isothiocyanate
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point139.00 to 140.00 °C. @ 11.00 mm HgThe Good Scents Company Information System
Water Solubility110 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP3.470The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane
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 IDDB12695
Phenol Explorer Compound IDNot Available
FooDB IDFDB004307
KNApSAcK IDC00057265
Chemspider ID15870
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPhenethyl_isothiocyanate
METLIN IDNot Available
PubChem Compound16741
PDB IDNot Available
ChEBI ID351346
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1049131
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .