Hmdb loader

Showing metabocard for Allyl isothiocyanate (HMDB0005843)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2007-04-12 15:38:43 UTC
Update Date2023-02-21 17:17:09 UTC
HMDB IDHMDB0005843
Secondary Accession Numbers
  • HMDB05843
Metabolite Identification
Common NameAllyl isothiocyanate
DescriptionAllyl isothiocyanate is a volatile organic compound. Allyl isothiocyanate (AITC) is a constituent of mustard, horseradish and wasabi and certain vegetables found in the human diet, mostly in cruciferous vegetables. AITC is a colorless to pale yellow liquid that is slightly soluble in water, but soluble in most organic solvents. AITC possesses numerous biochemical and physiological activities. It is cytotoxic and tumorigenic at high doses and is also a modulator of enzymes involved in metabolism of xenobiotics, including carcinogens. It is plausible that the wide consumption of dietary AITC may have profound effects on human health. oxidative DNA damage may play important roles in carcinogenic processes induced by AITC. Allergic contact dermatitis from AICT is well known but infrequently reported. AITC is occasionally found as a volatile component of normal human biofluids. (PMID:5556886 , 8222057 , 8000299 , 10754276 , 15373848 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005843 (Allyl isothiocyanate)

  Mrv1652305271900022D          

  6  5  0  0  0  0            999 V2000
   19.5231   -4.2764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0942   -3.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3798   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6652   -3.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9507   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8088   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
Download

3D MOL for HMDB0005843 (Allyl isothiocyanate)

HMDB0005843
     RDKit          3D
Allyl isothiocyanate
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.1005    0.9828   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592   -0.3132   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -1.0974    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.2309    1.0683 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    0.3384    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.6036    0.2117 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    1.5196   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582    1.5219    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.8294   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643   -1.5672   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524   -1.9281    0.8255 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  2  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
M  END
Download

3D SDF for HMDB0005843 (Allyl isothiocyanate)

  Mrv1652305271900022D          

  6  5  0  0  0  0            999 V2000
   19.5231   -4.2764    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0942   -3.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3798   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6652   -3.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9507   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8088   -3.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  2  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005843

> <DATABASE_NAME>
hmdb

> <SMILES>
C=CCN=C=S

> <INCHI_IDENTIFIER>
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2

> <INCHI_KEY>
ZOJBYZNEUISWFT-UHFFFAOYSA-N

> <FORMULA>
C4H5NS

> <MOLECULAR_WEIGHT>
99.154

> <EXACT_MASS>
99.014269855

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
11

> <JCHEM_AVERAGE_POLARIZABILITY>
10.514580270585387

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-isothiocyanatoprop-1-ene

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
1.8008998773333331

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8517148435124207

> <JCHEM_POLAR_SURFACE_AREA>
12.36

> <JCHEM_REFRACTIVITY>
30.491799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
allyl isothiocyanate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005843 (Allyl isothiocyanate)

HMDB0005843
     RDKit          3D
Allyl isothiocyanate
 11 10  0  0  0  0  0  0  0  0999 V2000
   -1.1005    0.9828   -0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9592   -0.3132   -0.4847 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0906   -1.0974    0.2280 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.2309    1.0683 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    0.3384    0.5846 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7963    1.6036    0.2117 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    1.5196   -0.8305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4582    1.5219    0.3710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204   -0.8294   -1.1693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7643   -1.5672   -0.5020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3524   -1.9281    0.8255 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  2  0
  5  6  2  0
  1  7  1  0
  1  8  1  0
  2  9  1  0
  3 10  1  0
  3 11  1  0
M  END
Download

PDB for HMDB0005843 (Allyl isothiocyanate)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  S   UNK     0      36.443  -7.983   0.000  0.00  0.00           S+0
HETATM    2  N   UNK     0      33.776  -6.443   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      32.442  -7.213   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      31.108  -6.443   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.775  -7.213   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.110  -7.213   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    3    6                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    1    2                                                       
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
Download

3D PDB for HMDB0005843 (Allyl isothiocyanate)

COMPND    HMDB0005843
HETATM    1  C1  UNL     1      -1.100   0.983  -0.303  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.959  -0.313  -0.485  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.091  -1.097   0.228  1.00  0.00           C  
HETATM    4  N1  UNL     1       0.839  -0.231   1.068  1.00  0.00           N  
HETATM    5  C4  UNL     1       1.867   0.338   0.585  1.00  0.00           C  
HETATM    6  S1  UNL     1       2.796   1.604   0.212  1.00  0.00           S  
HETATM    7  H1  UNL     1      -1.866   1.520  -0.830  1.00  0.00           H  
HETATM    8  H2  UNL     1      -0.458   1.522   0.371  1.00  0.00           H  
HETATM    9  H3  UNL     1      -1.620  -0.829  -1.169  1.00  0.00           H  
HETATM   10  H4  UNL     1       0.764  -1.567  -0.502  1.00  0.00           H  
HETATM   11  H5  UNL     1      -0.352  -1.928   0.826  1.00  0.00           H  
CONECT    1    2    2    7    8
CONECT    2    3    9
CONECT    3    4   10   11
CONECT    4    5    5
CONECT    5    6    6
END
Download

SMILES for HMDB0005843 (Allyl isothiocyanate)

C=CCN=C=S
Download

INCHI for HMDB0005843 (Allyl isothiocyanate)

InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
Download
View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC4H5NS
Average Molecular Weight99.154
Monoisotopic Molecular Weight99.014269855
IUPAC Name3-isothiocyanatoprop-1-ene
Traditional Nameallyl isothiocyanate
CAS Registry Number57-06-7
SMILES
C=CCN=C=S
InChI Identifier
InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
InChI KeyZOJBYZNEUISWFT-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
Health effectOrganoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-80 °CNot Available
Boiling Point150.00 to 152.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 20 °CNot Available
LogP2.150The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.14 +/- 0.098 uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB012440
KNApSAcK IDNot Available
Chemspider ID21105854
KEGG Compound IDC19317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAllyl_isothiocyanate
METLIN IDNot Available
PubChem Compound5971
PDB IDNot Available
ChEBI ID73224
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002981
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Zlatkis A, Liebich HM: Profile of volatile metabolites in human urine. Clin Chem. 1971 Jul;17(7):592-4. [PubMed:5556886 ]
  2. Jiao D, Ho CT, Foiles P, Chung FL: Identification and quantification of the N-acetylcysteine conjugate of allyl isothiocyanate in human urine after ingestion of mustard. Cancer Epidemiol Biomarkers Prev. 1994 Sep;3(6):487-92. [PubMed:8000299 ]
  3. Musk SR, Johnson IT: Allyl isothiocyanate is selectively toxic to transformed cells of the human colorectal tumour line HT29. Carcinogenesis. 1993 Oct;14(10):2079-83. [PubMed:8222057 ]
  4. Murata M, Yamashita N, Inoue S, Kawanishi S: Mechanism of oxidative DNA damage induced by carcinogenic allyl isothiocyanate. Free Radic Biol Med. 2000 Mar 1;28(5):797-805. [PubMed:10754276 ]
  5. Lerbaek A, Rastogi SC, Menne T: Allergic contact dermatitis from allyl isothiocyanate in a Danish cohort of 259 selected patients. Contact Dermatitis. 2004 Aug;51(2):79-83. [PubMed:15373848 ]