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Showing metabocard for 4-Isothiocyanato-1-butene (HMDB0033867)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:26 UTC
Update Date2023-02-21 17:23:43 UTC
HMDB IDHMDB0033867
Secondary Accession Numbers
  • HMDB33867
Metabolite Identification
Common Name4-Isothiocyanato-1-butene
Description4-Isothiocyanato-1-butene 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. 4-Isothiocyanato-1-butene is an aromatic and pungent tasting compound. 4-Isothiocyanato-1-butene has been detected, but not quantified in, several different foods, such as brassicas, cabbages (Brassica oleracea var. capitata), cauliflowers (Brassica oleracea var. botrytis), horseradishes (Armoracia rusticana), and white cabbages (Brassica oleracea L. var. capitata L. f. alba DC.). This could make 4-isothiocyanato-1-butene a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 4-Isothiocyanato-1-butene.
Structure
Data?1677000223
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0033867 (4-Isothiocyanato-1-butene)


  Mrv0541 05061307242D          

  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  2  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 HMDB0033867 (4-Isothiocyanato-1-butene)

HMDB0033867
     RDKit          3D
4-Isothiocyanato-1-butene
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.3649    0.7439    0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5166   -0.2569    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140   -0.3239   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8832   -0.3296   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0461   -0.3911   -0.9547 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -0.0763   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.8649   -0.1195 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2593    1.5254   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942    0.8318    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -1.0782    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.5421   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5482   -1.2731   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428    0.4940    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8648   -1.2731    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
M  END
Download

3D SDF for HMDB0033867 (4-Isothiocyanato-1-butene)


  Mrv0541 05061307242D          

  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  2  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>
HMDB0033867

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CCCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2

> <INCHI_KEY>
SKIHGKNFJKJXPX-UHFFFAOYSA-N

> <FORMULA>
C5H7NS

> <MOLECULAR_WEIGHT>
113.181

> <EXACT_MASS>
113.029919919

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
12.442994924553336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-isothiocyanatobut-1-ene

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.0895610823333333

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1133055964788494

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
35.2468

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-butene, 4-isothiocyanato-

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0033867 (4-Isothiocyanato-1-butene)

HMDB0033867
     RDKit          3D
4-Isothiocyanato-1-butene
 14 13  0  0  0  0  0  0  0  0999 V2000
   -2.3649    0.7439    0.0850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5166   -0.2569    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4140   -0.3239   -0.9044 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8832   -0.3296   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0461   -0.3911   -0.9547 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -0.0763   -0.4476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4470    0.8649   -0.1195 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2593    1.5254   -0.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1942    0.8318    0.8040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -1.0782    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4845    0.5421   -1.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5482   -1.2731   -1.4587 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9428    0.4940    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8648   -1.2731    0.4851 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  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
  2 10  1  0
  3 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
M  END
Download

PDB for HMDB0033867 (4-Isothiocyanato-1-butene)

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 HMDB0033867 (4-Isothiocyanato-1-butene)

COMPND    HMDB0033867
HETATM    1  C1  UNL     1      -2.365   0.744   0.085  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.517  -0.257   0.092  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.414  -0.324  -0.904  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.883  -0.330  -0.134  1.00  0.00           C  
HETATM    5  N1  UNL     1       2.046  -0.391  -0.955  1.00  0.00           N  
HETATM    6  C5  UNL     1       3.167  -0.076  -0.448  1.00  0.00           C  
HETATM    7  S1  UNL     1       4.447   0.865  -0.119  1.00  0.00           S  
HETATM    8  H1  UNL     1      -2.259   1.525  -0.653  1.00  0.00           H  
HETATM    9  H2  UNL     1      -3.194   0.832   0.804  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.569  -1.078   0.811  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.485   0.542  -1.601  1.00  0.00           H  
HETATM   12  H5  UNL     1      -0.548  -1.273  -1.459  1.00  0.00           H  
HETATM   13  H6  UNL     1       0.943   0.494   0.587  1.00  0.00           H  
HETATM   14  H7  UNL     1       0.865  -1.273   0.485  1.00  0.00           H  
CONECT    1    2    2    8    9
CONECT    2    3   10
CONECT    3    4   11   12
CONECT    4    5   13   14
CONECT    5    6    6
CONECT    6    7    7
END
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SMILES for HMDB0033867 (4-Isothiocyanato-1-butene)

C=CCCN=C=S
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INCHI for HMDB0033867 (4-Isothiocyanato-1-butene)

InChI=1S/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Butene 4-isothiocyanateHMDB
1-Butene-4-isothiocyanateHMDB
3-Butenyl isothiocyanateHMDB
But-3-enyl isothiocyanateHMDB
Crotonyl mustard oilHMDB
Crotyl mustard oilHMDB
Isothiocyanic acid, 3-butenyl esterHMDB
BylITCMeSH, HMDB
ButenylisothiocyanateMeSH, HMDB
Chemical FormulaC5H7NS
Average Molecular Weight113.181
Monoisotopic Molecular Weight113.029919919
IUPAC Name4-isothiocyanatobut-1-ene
Traditional Name1-butene, 4-isothiocyanato-
CAS Registry Number3386-97-8
SMILES
C=CCCN=C=S
InChI Identifier
InChI=1S/C5H7NS/c1-2-3-4-6-5-7/h2H,1,3-4H2
InChI KeySKIHGKNFJKJXPX-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
Role
Biological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point163.00 to 164.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.46 mg/mL at 20 °CNot Available
LogP2.692 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.16 g/LALOGPS
logP2.41ALOGPS
logP2.09ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity35.25 m³·mol⁻¹ChemAxon
Polarizability12.44 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]+122.62531661259
DarkChem[M-H]-120.1331661259
DeepCCS[M+H]+127.13730932474
DeepCCS[M-H]-125.18530932474
DeepCCS[M-2H]-160.67430932474
DeepCCS[M+Na]+134.8430932474
AllCCS[M+H]+126.232859911
AllCCS[M+H-H2O]+121.932859911
AllCCS[M+NH4]+130.232859911
AllCCS[M+Na]+131.432859911
AllCCS[M-H]-130.632859911
AllCCS[M+Na-2H]-134.532859911
AllCCS[M+HCOO]-138.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Isothiocyanato-1-buteneC=CCCN=C=S1494.2Standard polar33892256
4-Isothiocyanato-1-buteneC=CCCN=C=S954.4Standard non polar33892256
4-Isothiocyanato-1-buteneC=CCCN=C=S969.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Isothiocyanato-1-butene EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Isothiocyanato-1-butene EI-B (Non-derivatized)splash10-05fr-9200000000-1a40200ada4e3470682d2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isothiocyanato-1-butene GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bf-9000000000-8f560f490ac3ff773e2d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Isothiocyanato-1-butene 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 - 4-Isothiocyanato-1-butene 10V, Positive-QTOFsplash10-03di-5900000000-6b5a0c36ac97abfbfafd2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 20V, Positive-QTOFsplash10-0a4i-9200000000-107fe6a8c4c497549b8f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 40V, Positive-QTOFsplash10-0a4i-9000000000-a06462555fc1d0881d1c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 10V, Negative-QTOFsplash10-03di-3900000000-2fd61d6aae4db1e2552b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 20V, Negative-QTOFsplash10-08fr-9400000000-b269adb37f1cf3ae532b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 40V, Negative-QTOFsplash10-0a4i-9000000000-ab47c48091b0e907f16e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 10V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 20V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 10V, Positive-QTOFsplash10-03di-8900000000-aca8f379641b5eeb32072021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 20V, Positive-QTOFsplash10-0a59-9000000000-d5971d80ffef88e54fb22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Isothiocyanato-1-butene 40V, Positive-QTOFsplash10-05fr-9000000000-b0672f53f73beb8ccafa2021-09-23Wishart 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
  • Cytoplasm
  • Extracellular
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 IDFDB012051
KNApSAcK IDC00052675
Chemspider ID69373
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76922
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1586801
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.. .