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Showing metabocard for Isobutyl isothiocyanate (HMDB0032345)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:18 UTC
Update Date2023-02-21 17:21:57 UTC
HMDB IDHMDB0032345
Secondary Accession Numbers
  • HMDB32345
Metabolite Identification
Common NameIsobutyl isothiocyanate
DescriptionIsobutyl 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. Isobutyl isothiocyanate is a green tasting compound. Isobutyl isothiocyanate is found, on average, in the highest concentration within soft-necked garlics (Allium sativum L. var. sativum). Isobutyl isothiocyanate has also been detected, but not quantified in, cauliflowers (Brassica oleracea var. botrytis). This could make isobutyl isothiocyanate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Isobutyl isothiocyanate.
Structure
Data?1677000116
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032345 (Isobutyl isothiocyanate)


  Mrv0541 05061306282D          

  7  6  0  0  0  0            999 V2000
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    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
   -1.2375   -0.7145    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
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  2  0  0  0  0
M  END
Download

3D MOL for HMDB0032345 (Isobutyl isothiocyanate)

HMDB0032345
     RDKit          3D
Isobutyl isothiocyanate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0713   -0.1332    1.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215   -0.1353   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    1.1933   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.6210   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984    0.1536    0.0837 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364   -0.3468    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -1.2002    1.1846 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888    0.6254    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4810   -1.1029    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.1263    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197   -0.8557   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142    1.8954   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    1.6127   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184    0.9913   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8020   -0.5118   -1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -1.6910   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 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 HMDB0032345 (Isobutyl isothiocyanate)


  Mrv0541 05061306282D          

  7  6  0  0  0  0            999 V2000
   -1.6500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    0.0000    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
   -1.2375   -0.7145    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
  5  1  1  0  0  0  0
  5  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  3  1  0  0  0  0
  6  4  2  0  0  0  0
  7  4  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032345

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C5H9NS/c1-5(2)3-6-4-7/h5H,3H2,1-2H3

> <INCHI_KEY>
NSDDRJXKROCWRZ-UHFFFAOYSA-N

> <FORMULA>
C5H9NS

> <MOLECULAR_WEIGHT>
115.197

> <EXACT_MASS>
115.045569983

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.169272705696544

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-isothiocyanato-2-methylpropane

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
2.31395323

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9502671736081254

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
35.073299999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-isothiocyanato-2-methylpropane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0032345 (Isobutyl isothiocyanate)

HMDB0032345
     RDKit          3D
Isobutyl isothiocyanate
 16 15  0  0  0  0  0  0  0  0999 V2000
   -1.0713   -0.1332    1.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7215   -0.1353   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9210    1.1933   -0.8965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6707   -0.6210   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984    0.1536    0.0837 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8364   -0.3468    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9651   -1.2002    1.1846 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8888    0.6254    1.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4810   -1.1029    1.5620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2437    0.1263    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4197   -0.8557   -0.7441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1142    1.8954   -0.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355    1.6127   -0.6903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9184    0.9913   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8020   -0.5118   -1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -1.6910   -0.3251 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  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
  3 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 HMDB0032345 (Isobutyl isothiocyanate)

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      -3.080  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310  -1.334   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    5                                                            
CONECT    2    5                                                            
CONECT    3    5    6                                                       
CONECT    4    6    7                                                       
CONECT    5    1    2    3                                                  
CONECT    6    3    4                                                       
CONECT    7    4                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for HMDB0032345 (Isobutyl isothiocyanate)

COMPND    HMDB0032345
HETATM    1  C1  UNL     1      -1.071  -0.133   1.213  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.722  -0.135  -0.229  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.921   1.193  -0.896  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.671  -0.621  -0.530  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.698   0.154   0.084  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.836  -0.347   0.395  1.00  0.00           C  
HETATM    7  S1  UNL     1       3.965  -1.200   1.185  1.00  0.00           S  
HETATM    8  H1  UNL     1      -1.889   0.625   1.390  1.00  0.00           H  
HETATM    9  H2  UNL     1      -1.481  -1.103   1.562  1.00  0.00           H  
HETATM   10  H3  UNL     1      -0.244   0.126   1.887  1.00  0.00           H  
HETATM   11  H4  UNL     1      -1.420  -0.856  -0.744  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.114   1.895  -0.646  1.00  0.00           H  
HETATM   13  H6  UNL     1      -1.936   1.613  -0.690  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.918   0.991  -2.007  1.00  0.00           H  
HETATM   15  H8  UNL     1       0.802  -0.512  -1.647  1.00  0.00           H  
HETATM   16  H9  UNL     1       0.742  -1.691  -0.325  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    4   11
CONECT    3   12   13   14
CONECT    4    5   15   16
CONECT    5    6    6
CONECT    6    7    7
END
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SMILES for HMDB0032345 (Isobutyl isothiocyanate)

CC(C)CN=C=S
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INCHI for HMDB0032345 (Isobutyl isothiocyanate)

InChI=1S/C5H9NS/c1-5(2)3-6-4-7/h5H,3H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
Isobutyl isothiocyanic acidGenerator
1-isothiocyanato-2-Methyl-propaneHMDB
1-isothiocyanato-2-MethylpropaneHMDB
2-Methylpropyl isothiocyanateHMDB
I-butyl isothiocyanateHMDB
Isothiocyanic acid, isobutyl esterHMDB
Propane, 1-isothiocyanato-2-methyl- (9ci)HMDB
Thiocyanic acid, 2-methylpropyl esterHMDB
Chemical FormulaC5H9NS
Average Molecular Weight115.197
Monoisotopic Molecular Weight115.045569983
IUPAC Name1-isothiocyanato-2-methylpropane
Traditional Name1-isothiocyanato-2-methylpropane
CAS Registry Number591-82-2
SMILES
CC(C)CN=C=S
InChI Identifier
InChI=1S/C5H9NS/c1-5(2)3-6-4-7/h5H,3H2,1-2H3
InChI KeyNSDDRJXKROCWRZ-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 DescriptorsNot Available
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 PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.82Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.53 g/LALOGPS
logP2.57ALOGPS
logP2.31ChemAxon
logS-2.3ALOGPS
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity35.07 m³·mol⁻¹ChemAxon
Polarizability13.17 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]+123.93331661259
DarkChem[M-H]-118.21631661259
DeepCCS[M+H]+128.82730932474
DeepCCS[M-H]-126.85130932474
DeepCCS[M-2H]-162.42330932474
DeepCCS[M+Na]+136.82530932474
AllCCS[M+H]+125.832859911
AllCCS[M+H-H2O]+121.632859911
AllCCS[M+NH4]+129.732859911
AllCCS[M+Na]+130.832859911
AllCCS[M-H]-131.632859911
AllCCS[M+Na-2H]-135.732859911
AllCCS[M+HCOO]-140.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isobutyl isothiocyanateCC(C)CN=C=S1410.7Standard polar33892256
Isobutyl isothiocyanateCC(C)CN=C=S909.0Standard non polar33892256
Isobutyl isothiocyanateCC(C)CN=C=S947.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl isothiocyanate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9000000000-a658553b8abd107e0f622017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isobutyl isothiocyanate 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 - Isobutyl isothiocyanate 10V, Positive-QTOFsplash10-066r-5900000000-c41db98788b936425d082016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 20V, Positive-QTOFsplash10-0a4i-9100000000-97a0186a3758a101b8442016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 40V, Positive-QTOFsplash10-0a4i-9000000000-3dd66ef5aa8c2d9439b52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 10V, Negative-QTOFsplash10-03di-2900000000-db560f87c95c881627fa2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 20V, Negative-QTOFsplash10-08fr-8900000000-0cd0f9f47957c95e22922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-09559d186adbce832ff02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 10V, Negative-QTOFsplash10-03di-2900000000-d6de60ecb206d08e06152021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 20V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 10V, Positive-QTOFsplash10-014i-6900000000-bb6af81285fa888cce0a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 20V, Positive-QTOFsplash10-0a4i-9000000000-a894a387324982a8e8442021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isobutyl isothiocyanate 40V, Positive-QTOFsplash10-0ab9-9000000000-69bb2fd15475a0cd10ab2021-09-22Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB009641
KNApSAcK IDNot Available
Chemspider ID62183
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68960
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .