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Showing metabocard for Ethyl isothiocyanate (HMDB0303226)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 00:20:20 UTC
Update Date2021-09-24 00:20:20 UTC
HMDB IDHMDB0303226
Secondary Accession NumbersNone
Metabolite Identification
Common NameEthyl isothiocyanate
DescriptionEthyl isothiocyanate, also known as eitc or isothiocyanic acid, ethyl ester, is a member of the class of compounds known as isothiocyanates. Isothiocyanates are organic compounds containing the isothiocyanate group, an isocyanate analogue with the general formula RN=C=S. Ethyl isothiocyanate is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ethyl isothiocyanate is a garlic, mustard, and pungent tasting compound found in horseradish, which makes ethyl isothiocyanate a potential biomarker for the consumption of this food product.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0303226 (Ethyl isothiocyanate)


  Mrv0541 02241221052D          

  5  4  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 S   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
   -0.4125    0.7145    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
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
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3D MOL for HMDB0303226 (Ethyl isothiocyanate)

HMDB0303226
     RDKit          3D
Ethyl isothiocyanate
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.0312   -0.4240   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7134    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    0.8004   -0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   -0.0917   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -1.1430    0.3314 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.1791   -1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753   -1.3740   -0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -0.5073    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7966    1.6558    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607    0.5495    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
M  END
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3D SDF for HMDB0303226 (Ethyl isothiocyanate)


  Mrv0541 02241221052D          

  5  4  0  0  0  0            999 V2000
    1.6500    0.0000    0.0000 S   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
   -0.4125    0.7145    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
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303226

> <DATABASE_NAME>
hmdb

> <SMILES>
CCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C3H5NS/c1-2-4-3-5/h2H2,1H3

> <INCHI_KEY>
HBNYJWAFDZLWRS-UHFFFAOYSA-N

> <FORMULA>
C3H5NS

> <MOLECULAR_WEIGHT>
87.143

> <EXACT_MASS>
87.014269855

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
9.284183586814517

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
isothiocyanatoethane

> <ALOGPS_LOGP>
1.78

> <JCHEM_LOGP>
1.4264580086666665

> <ALOGPS_LOGS>
-1.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1005363282079235

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
26.0777

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isothiocyanatoethane

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0303226 (Ethyl isothiocyanate)

HMDB0303226
     RDKit          3D
Ethyl isothiocyanate
 10  9  0  0  0  0  0  0  0  0999 V2000
   -1.0312   -0.4240   -0.3004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2549    0.7134    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0108    0.8004   -0.3416 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9194   -0.0917   -0.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0138   -1.1430    0.3314 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2393   -0.1791   -1.3506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753   -1.3740   -0.2453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9861   -0.5073    0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7966    1.6558    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1607    0.5495    1.4301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  2  0
  1  6  1  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  2 10  1  0
M  END
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PDB for HMDB0303226 (Ethyl isothiocyanate)

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  S   UNK     0       3.080   0.000   0.000  0.00  0.00           S+0
HETATM    2  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      -0.770   1.334   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
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
MASTER        0    0    0    0    0    0    0    0    5    0    8    0
END
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3D PDB for HMDB0303226 (Ethyl isothiocyanate)

COMPND    HMDB0303226
HETATM    1  C1  UNL     1      -1.031  -0.424  -0.300  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.255   0.713   0.342  1.00  0.00           C  
HETATM    3  N1  UNL     1       1.011   0.800  -0.342  1.00  0.00           N  
HETATM    4  C3  UNL     1       1.919  -0.092  -0.268  1.00  0.00           C  
HETATM    5  S1  UNL     1       3.014  -1.143   0.331  1.00  0.00           S  
HETATM    6  H1  UNL     1      -1.239  -0.179  -1.351  1.00  0.00           H  
HETATM    7  H2  UNL     1      -0.475  -1.374  -0.245  1.00  0.00           H  
HETATM    8  H3  UNL     1      -1.986  -0.507   0.230  1.00  0.00           H  
HETATM    9  H4  UNL     1      -0.797   1.656   0.172  1.00  0.00           H  
HETATM   10  H5  UNL     1      -0.161   0.550   1.430  1.00  0.00           H  
CONECT    1    2    6    7    8
CONECT    2    3    9   10
CONECT    3    4    4
CONECT    4    5    5
END
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SMILES for HMDB0303226 (Ethyl isothiocyanate)

CCN=C=S
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INCHI for HMDB0303226 (Ethyl isothiocyanate)

InChI=1S/C3H5NS/c1-2-4-3-5/h2H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
EITCChEBI
Isothiocyanic acid, ethyl esterChEBI
Isothiocyanate, ethyl esterGenerator
Ethyl isothiocyanic acidGenerator
EthylisothiocyanateMeSH
Chemical FormulaC3H5NS
Average Molecular Weight87.143
Monoisotopic Molecular Weight87.014269855
IUPAC Nameisothiocyanatoethane
Traditional Nameisothiocyanatoethane
CAS Registry NumberNot Available
SMILES
CCN=C=S
InChI Identifier
InChI=1S/C3H5NS/c1-2-4-3-5/h2H2,1H3
InChI KeyHBNYJWAFDZLWRS-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
Source
ProcessNot Available
Role
Biological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.78ALOGPS
logP1.43ChemAxon
logS-1.8ALOGPS
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity26.08 m³·mol⁻¹ChemAxon
Polarizability9.28 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
AllCCS[M+H]+122.94232859911
AllCCS[M+H-H2O]+118.53532859911
AllCCS[M+Na]+128.24432859911
AllCCS[M+NH4]+127.05632859911
AllCCS[M-H]-136.94232859911
AllCCS[M+Na-2H]-142.57932859911
AllCCS[M+HCOO]-148.76432859911
DeepCCS[M+H]+121.31730932474
DeepCCS[M-H]-119.47730932474
DeepCCS[M-2H]-154.88530932474
DeepCCS[M+Na]+128.76330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 20229.8452 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.73 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1099.1 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid430.9 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid170.3 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid316.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid148.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid347.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid529.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)225.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid744.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid285.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid980.1 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid268.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid315.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate588.6 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA350.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water160.9 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 10V, Positive-QTOFsplash10-000i-9000000000-4585628da41fba3e20a42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 20V, Positive-QTOFsplash10-000i-9000000000-7cf44628ab049f8a98902016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 40V, Positive-QTOFsplash10-056r-9000000000-7a1395b7113808b2abcf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 10V, Negative-QTOFsplash10-000i-9000000000-e8e437ae77193a8d1e4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 20V, Negative-QTOFsplash10-052r-9000000000-0d544a1aa527999029412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-d2cda046199866c2bdfb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 10V, Positive-QTOFsplash10-052r-9000000000-d3073bec44fa78b1f66f2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 20V, Positive-QTOFsplash10-0a4i-9000000000-5c58097a39e9a3acf6752021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 40V, Positive-QTOFsplash10-0a4i-9000000000-5de8b72a59d83c75df272021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 10V, Negative-QTOFsplash10-0a4r-9000000000-96a9d62f794f8635c88b2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 20V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isothiocyanate 40V, Negative-QTOFsplash10-0a4i-9000000000-286b63d3516de7d14a122021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDFDB009395
KNApSAcK IDC00032761
Chemspider ID10501
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID85098
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1245361
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available