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Showing NP-Card for 1-Isothiocyanatobutane (NP0046149)

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Record Information
Version2.0
Created at2022-03-17 19:49:16 UTC
Updated at2022-03-17 19:49:16 UTC
NP-MRD IDNP0046149
Secondary Accession NumbersNone
Natural Product Identification
Common Name1-Isothiocyanatobutane
Description1-Isothiocyanatobutane, also known as BITC or N-butyl isothiocyanate, belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S. An isothiocyanate having a butyl group attached to the nitrogen. 1-Isothiocyanatobutane is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Isothiocyanatobutane is a citrus, earthy, and fatty tasting compound. Outside of the human body, 1-Isothiocyanatobutane is found, on average, in the highest concentration within horseradish. 1-Isothiocyanatobutane has also been detected, but not quantified in, a few different foods, such as brassicas, cabbages, and cauliflowers. 1-Isothiocyanatobutane is found in Brassica carinata, Capparis spinosa and Eutrema japonicum. 1-Isothiocyanatobutane was first documented in 1991 (PMID: 1774231). This could make 1-isothiocyanatobutane a potential biomarker for the consumption of these foods (PMID: 21109004).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0046149 (1-Isothiocyanatobutane)


  Mrv0541 05061305532D          

  7  6  0  0  0  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  2  0  0  0  0
M  END
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3D MOL for NP0046149 (1-Isothiocyanatobutane)

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3D SDF for NP0046149 (1-Isothiocyanatobutane)

  Mrv0541 05061305532D          

  7  6  0  0  0  0            999 V2000
   -2.4750   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.0000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  7  5  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0046149

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3

> <INCHI_KEY>
LIMQQADUEULBSO-UHFFFAOYSA-N

> <FORMULA>
C5H9NS

> <MOLECULAR_WEIGHT>
115.197

> <EXACT_MASS>
115.045569983

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.377472596441937

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-isothiocyanatobutane

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
2.393549068666667

> <ALOGPS_LOGS>
-2.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.869921969440296

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
35.2027

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butyl isothiocyanate

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0046149 (1-Isothiocyanatobutane)
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PDB for NP0046149 (1-Isothiocyanatobutane)
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      -4.620  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    7  S   UNK     0       3.080   0.000   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    6                                                       
CONECT    5    6    7                                                       
CONECT    6    4    5                                                       
CONECT    7    5                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END

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3D PDB for NP0046149 (1-Isothiocyanatobutane)
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SMILES for NP0046149 (1-Isothiocyanatobutane)
CCCCN=C=S
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INCHI for NP0046149 (1-Isothiocyanatobutane)
InChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3
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View in JSmol
Synonyms
ValueSource
BITCChEBI
BuNCSChEBI
Butyl mustard oilChEBI
ButylsenfoelChEBI
Isothiocyanic acid N-butyl esterChEBI
Isothiocyanic acid, butyl esterChEBI
N-Butyl isothiocyanateChEBI
Isothiocyanate N-butyl esterGenerator
Isothiocyanate, butyl esterGenerator
N-Butyl isothiocyanic acidGenerator
1-Isothiocyanato-butaneHMDB
Butyl isothiocyanateHMDB
Butyl isothiocyanate, 8ciHMDB
Tert-butyl isothiocyanateHMDB
TBITC CPDHMDB
Butyl isothiocyanic acidGenerator
Chemical FormulaC5H9NS
Average Mass115.1970 Da
Monoisotopic Mass115.04557 Da
IUPAC Name1-isothiocyanatobutane
Traditional Namebutyl isothiocyanate
CAS Registry Number592-82-5
SMILES
CCCCN=C=S
InChI Identifier
InChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3
InChI KeyLIMQQADUEULBSO-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Armoracia rusticanaFooDB
Brassica carinataLOTUS Database
Brassica oleracea var. botrytisFooDB
Capparis spinosaLOTUS Database
Eutrema japonicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isothiocyanates. These are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S.
KingdomOrganic compounds  
Super ClassOrganosulfur compounds  
ClassIsothiocyanates  
Sub ClassNot Available
Direct ParentIsothiocyanates  
Alternative Parents
Substituents
  • Isothiocyanate
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP2.86ALOGPS
logP2.39ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.2 m³·mol⁻¹ChemAxon
Polarizability13.38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0031328  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003390  
KNApSAcK IDNot Available
Chemspider ID11124  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11613  
PDB IDNot Available
ChEBI ID50534  
Good Scents IDNot Available
References
General References
  1. Lawrence JF, Menard C: Confirmation of domoic acid in shellfish using butyl isothiocyanate and reversed-phase liquid chromatography. J Chromatogr. 1991 Jul 26;550(1-2):595-601. doi: 10.1016/s0021-9673(01)88565-4. [PubMed:1774231  ] 
  2. Ernst IM, Wagner AE, Schuemann C, Storm N, Hoppner W, Doring F, Stocker A, Rimbach G: Allyl-, butyl- and phenylethyl-isothiocyanate activate Nrf2 in cultured fibroblasts. Pharmacol Res. 2011 Mar;63(3):233-40. doi: 10.1016/j.phrs.2010.11.005. Epub 2010  Nov 23. [PubMed:21109004  ]