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Showing NP-Card for 3-Benzylisothiocyanate (NP0046373)

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Record Information
Version2.0
Created at2022-03-17 19:56:58 UTC
Updated at2022-03-17 19:56:58 UTC
NP-MRD IDNP0046373
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Benzylisothiocyanate
DescriptionBenzyl isothiocyanate, also known as benzylsenfoel or a-isothiocyanatotoluene, 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. Benzyl isothiocyanate is an extremely weak basic (essentially neutral) compound (based on its pKa). A recent published study showed its impact on obesity, fatty liver, and insulin resistance in diet-induced obesity mouse model. Outside of the human body, Benzyl isothiocyanate has been detected, but not quantified in, horseradish. This could make benzyl isothiocyanate a potential biomarker for the consumption of these foods. Benzyl isothiocyanate, and other isothiocyanates in general, were found to be protective against pancreatic carcinogenesis in vitro via expression of p21/WAF1 gene. Benzyl isothiocyanate (BITC) is an isothiocyanate found in plants of the mustard family. 3-Benzylisothiocyanate is found in Acanthella cavernosa, Allium cepa, Brassica juncea , Carica papaya, Carica papaya , Descurainia sophia , Erucaria microcarpa, Lepidium apetalum, Lepidium meyenii, Lepidium meyenii Maca , Lepidium sativumt, Moringa oleifera , Moringa peregrine, Moringa stenopetala , Pentadiplandra brazzeana, Simicratea welwitschii, Sinapis alba and Tropaeolum majus . It can be found in Alliaria petiolata, pilu oil, and papaya seeds where it is the main product of the glucotropaeolin breakdown by the enzyme myrosinase.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046373 (3-Benzylisothiocyanate)


  Mrv0541 05061307282D          

 10 10  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
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  2  0  0  0  0
M  END
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3D MOL for NP0046373 (3-Benzylisothiocyanate)

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3D SDF for NP0046373 (3-Benzylisothiocyanate)

  Mrv0541 05061307282D          

 10 10  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
    0.0000    3.3000    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
    0.0000    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    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
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  7  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
S=C=NCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2

> <INCHI_KEY>
MDKCFLQDBWCQCV-UHFFFAOYSA-N

> <FORMULA>
C8H7NS

> <MOLECULAR_WEIGHT>
149.213

> <EXACT_MASS>
149.029919919

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
16.15908151966592

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(isothiocyanatomethyl)benzene

> <ALOGPS_LOGP>
3.22

> <JCHEM_LOGP>
2.794123171333333

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.163156684995442

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
45.9417

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl isothiocyanate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046373 (3-Benzylisothiocyanate)
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PDB for NP0046373 (3-Benzylisothiocyanate)
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   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   4.620   0.000  0.00  0.00           N+0
HETATM   10  S   UNK     0       0.000   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    8                                                       
CONECT    5    3    8                                                       
CONECT    6    8    9                                                       
CONECT    7    9   10                                                       
CONECT    8    4    5    6                                                  
CONECT    9    6    7                                                       
CONECT   10    7                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END

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3D PDB for NP0046373 (3-Benzylisothiocyanate)
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SMILES for NP0046373 (3-Benzylisothiocyanate)
S=C=NCC1=CC=CC=C1
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INCHI for NP0046373 (3-Benzylisothiocyanate)
InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
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View in JSmol
Synonyms
ValueSource
alpha-IsothiocyanatotolueneChEBI
BenzylsenfoelChEBI
Isothiocyanic acid, benzyl esterChEBI
a-IsothiocyanatotolueneGenerator
Α-isothiocyanatotolueneGenerator
Isothiocyanate, benzyl esterGenerator
Benzyl isothiocyanic acidGenerator
(Isothiocyanatomethyl)-benzeneHMDB
(Isothiocyanatomethyl)benzeneHMDB
(Isothiocyanatomethyl)benzene, 9ciHMDB
AB 2HMDB
alpha-Isothiocyanato-tolueneHMDB
Benzyl isothio cyanateHMDB
Benzyl mustard oilHMDB
Benzyl-isothiocyanateHMDB
BenzylisothiocyanateHMDB
Isothiocyanato-methyl-benzeneHMDB
Isothiocyanic acid benzyl esterHMDB
IsothiocyanotaomethylbenzeneHMDB
Phenylmethyl isothiocyanateHMDB
Pmitc CPDHMDB
TromacapsHMDB
TromalytHMDB
Tromalyt active substanceHMDB
TromocapsHMDB
UrogranHMDB
3-Benzylisothiocyanic acidGenerator
Chemical FormulaC8H7NS
Average Mass149.2130 Da
Monoisotopic Mass149.02992 Da
IUPAC Name(isothiocyanatomethyl)benzene
Traditional Namebenzyl isothiocyanate
CAS Registry Number622-78-6
SMILES
S=C=NCC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NS/c10-7-9-6-8-4-2-1-3-5-8/h1-5H,6H2
InChI KeyMDKCFLQDBWCQCV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Acanthella cavernosaLOTUS Database
Allium cepaLOTUS Database
Armoracia rusticanaFooDB
Brassica junceaPlant
Carica papayaLOTUS Database
Carica papaya L.Plant
Descurainia SophiaPlant
Erucaria microcarpaLOTUS Database
Lepidium apetalumPlant
Lepidium meyeniiLOTUS Database
Lepidium meyenii MacaPlant
Lepidium sativumFooDB
Lepidium sativumtPlant
Moringa oleiferaPlant
Moringa peregrinaPlant
Moringa stenopetalaPlant
Pentadiplandra brazzeanaLOTUS Database
Simicratea welwitschiiLOTUS Database
Sinapis albaLOTUS Database
Tropaeolum majusPlant
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
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
logP3.22ALOGPS
logP2.79ChemAxon
logS-3.4ALOGPS
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity45.94 m³·mol⁻¹ChemAxon
Polarizability16.16 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033969  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004133  
KNApSAcK IDC00007675  
Chemspider ID2256  
KEGG Compound IDC03098  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzyl isothiocyanate  
METLIN IDNot Available
PubChem Compound2346  
PDB IDNot Available
ChEBI ID17484  
Good Scents IDNot Available
References
General ReferencesNot Available