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Showing metabocard for 1-Isothiocyanatobutane (HMDB0031328)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:42:21 UTC
Update Date2023-02-21 17:20:24 UTC
HMDB IDHMDB0031328
Secondary Accession Numbers
  • HMDB31328
Metabolite Identification
Common Name1-Isothiocyanatobutane
Description1-Isothiocyanatobutane, also known as BITC or buncs, 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. 1-Isothiocyanatobutane is a citrus, earthy, and fatty tasting compound. 1-Isothiocyanatobutane is found, on average, in the highest concentration within horseradishes (Armoracia rusticana). 1-Isothiocyanatobutane has also been detected, but not quantified in, a few different foods, such as brassicas, cabbages (Brassica oleracea var. capitata), and cauliflowers (Brassica oleracea var. botrytis). This could make 1-isothiocyanatobutane a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 1-Isothiocyanatobutane.
Structure
Data?1677000024
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031328 (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
Download

3D MOL for HMDB0031328 (1-Isothiocyanatobutane)

HMDB0031328
     RDKit          3D
1-Isothiocyanatobutane
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.7741    0.2903   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.6898    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1498   -1.1982   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.0819   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    0.6135    0.5515 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072    1.5997    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    3.1724    0.2334 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    0.3325   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066    1.3210    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8610    0.0105   -0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5561   -0.2289    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -1.5383    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.9401    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -1.7276   -1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.6143   -1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -0.5495   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
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3D SDF for HMDB0031328 (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>
HMDB0031328

> <DATABASE_NAME>
hmdb

> <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 HMDB0031328 (1-Isothiocyanatobutane)

HMDB0031328
     RDKit          3D
1-Isothiocyanatobutane
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.7741    0.2903   -0.1344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9999   -0.6898    0.7019 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1498   -1.1982   -0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0703   -0.0819   -0.5688 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484    0.6135    0.5515 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4072    1.5997    0.2959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8266    3.1724    0.2334 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4727    0.3325   -1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7066    1.3210    0.3119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8610    0.0105   -0.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5561   -0.2289    1.6083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6045   -1.5383    1.0310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7011   -1.9401    0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2730   -1.7276   -1.0099 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5468    0.6143   -1.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8977   -0.5495   -1.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  2  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
M  END
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PDB for HMDB0031328 (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 HMDB0031328 (1-Isothiocyanatobutane)

COMPND    HMDB0031328
HETATM    1  C1  UNL     1      -1.774   0.290  -0.134  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.000  -0.690   0.702  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.150  -1.198  -0.134  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.070  -0.082  -0.569  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.648   0.614   0.552  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.407   1.600   0.296  1.00  0.00           C  
HETATM    7  S1  UNL     1       2.827   3.172   0.233  1.00  0.00           S  
HETATM    8  H1  UNL     1      -1.473   0.332  -1.183  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.707   1.321   0.312  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.861   0.011  -0.048  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.556  -0.229   1.608  1.00  0.00           H  
HETATM   12  H5  UNL     1      -1.604  -1.538   1.031  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.701  -1.940   0.468  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.273  -1.728  -1.010  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.547   0.614  -1.238  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.898  -0.550  -1.139  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4   13   14
CONECT    4    5   15   16
CONECT    5    6    6
CONECT    6    7    7
END
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SMILES for HMDB0031328 (1-Isothiocyanatobutane)

CCCCN=C=S
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INCHI for HMDB0031328 (1-Isothiocyanatobutane)

InChI=1S/C5H9NS/c1-2-3-4-6-5-7/h2-4H2,1H3
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View in JSmolView Stereo Labels
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
TBITC CPDMeSH
Tert-butyl isothiocyanateMeSH
1-isothiocyanato-ButaneHMDB
Butyl isothiocyanateHMDB
Butyl isothiocyanate, 8ciHMDB
Butyl isothiocyanic acidGenerator
Chemical FormulaC5H9NS
Average Molecular Weight115.197
Monoisotopic Molecular Weight115.045569983
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point168.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility335.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.92Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.33 g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+122.88431661259
DarkChem[M-H]-119.15331661259
DeepCCS[M+H]+129.73530932474
DeepCCS[M-H]-127.85330932474
DeepCCS[M-2H]-163.26830932474
DeepCCS[M+Na]+137.42930932474
AllCCS[M+H]+126.932859911
AllCCS[M+H-H2O]+122.732859911
AllCCS[M+NH4]+130.932859911
AllCCS[M+Na]+132.032859911
AllCCS[M-H]-133.332859911
AllCCS[M+Na-2H]-137.232859911
AllCCS[M+HCOO]-141.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-IsothiocyanatobutaneCCCCN=C=S1319.5Standard polar33892256
1-IsothiocyanatobutaneCCCCN=C=S947.4Standard non polar33892256
1-IsothiocyanatobutaneCCCCN=C=S975.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Isothiocyanatobutane GC-MS (Non-derivatized) - 70eV, Positivesplash10-054o-9000000000-560d0620f11fca8bf0812017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Isothiocyanatobutane GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 10V, Positive-QTOFsplash10-014i-4900000000-eb58ea6e66635e47ce262016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 20V, Positive-QTOFsplash10-0a4i-9200000000-fb596a2252e6005219fc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 40V, Positive-QTOFsplash10-0a4i-9000000000-2eea33fc6554478f434c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 10V, Negative-QTOFsplash10-03di-3900000000-ac70a67f3404af2235e42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 20V, Negative-QTOFsplash10-08fr-9500000000-aece654d61547421b82a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 40V, Negative-QTOFsplash10-0a4i-9000000000-02f332b3b3a55984d9a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 10V, Positive-QTOFsplash10-014i-5900000000-c8aeec829a815978ba682021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 20V, Positive-QTOFsplash10-0a4i-9000000000-24317ff79d02e63773052021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 40V, Positive-QTOFsplash10-00di-9000000000-705a4be681e05422e8852021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 10V, Negative-QTOFsplash10-03di-0900000000-b06b82844c0f8177681e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 20V, Negative-QTOFsplash10-0a4i-9200000000-4d7524c3cb79108954b62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Isothiocyanatobutane 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1226161
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.. .