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Showing metabocard for Allyl isothiocyanate (HMDB0005843)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
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
Data?1676999829
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
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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
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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

$$$$
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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
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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
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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
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SMILES for HMDB0005843 (Allyl isothiocyanate)

C=CCN=C=S
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INCHI for HMDB0005843 (Allyl isothiocyanate)

InChI=1S/C4H5NS/c1-2-3-5-4-6/h2H,1,3H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2-Propenyl isothiocyanateChEBI
3-Isothiocyanato-1-propeneChEBI
AITChEBI
AITCChEBI
Allyl isosulfocyanateChEBI
Allyl mustard oilChEBI
AllylsenfoelChEBI
Isothiocyanate d'allyleChEBI
Isothiocyanic acid allyl esterChEBI
Mustard oilChEBI
Oil OF mustardChEBI
Oleum sinapisChEBI
Senf oelChEBI
Volatile mustard oilChEBI
Volatile oil OF mustardChEBI
2-Propenyl isothiocyanic acidGenerator
Allyl isosulfocyanic acidGenerator
Allyl isosulphocyanateGenerator
Allyl isosulphocyanic acidGenerator
Isothiocyanic acid d'allyleGenerator
Isothiocyanate allyl esterGenerator
Allyl isothiocyanic acidGenerator
3-iso-Thiocyanatoprop-1-eneHMDB
3-Isothiocyanatoprop-1-eneHMDB
Allyl isothiocyanate (natural)HMDB
Allyl isothiocyanate non-perfume gradeHMDB
Allyl sevenolumHMDB
AllylsenevolHMDB, MeSH
AllylsevenolumHMDB
AllyspolHMDB
Artificial mustard oilHMDB
CarbospolHMDB
Caswell no. 027HMDB
FEMA no. 2034HMDB
IsothiocyansaeureallylesterHMDB
Oleum sinapis volatileHMDB
RedskinHMDB
SenfoelHMDB
Synthetic mustard oilHMDB
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
Not AvailableNot Available
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
PropertyValueSource
Water Solubility0.32 g/LALOGPS
logP1.9ALOGPS
logP1.8ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area12.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity30.49 m³·mol⁻¹ChemAxon
Polarizability10.51 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]+118.68531661259
DarkChem[M-H]-115.01131661259
DeepCCS[M+H]+124.3630932474
DeepCCS[M-H]-122.47230932474
DeepCCS[M-2H]-157.93630932474
DeepCCS[M+Na]+132.00230932474
AllCCS[M+H]+123.632859911
AllCCS[M+H-H2O]+119.232859911
AllCCS[M+NH4]+127.732859911
AllCCS[M+Na]+128.932859911
AllCCS[M-H]-130.132859911
AllCCS[M+Na-2H]-134.732859911
AllCCS[M+HCOO]-139.832859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.52 minutes32390414
Predicted by Siyang on May 30, 202210.5519 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.03 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid92.0 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1195.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid430.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid172.9 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid316.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid177.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid345.5 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 Acid538.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)250.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid852.0 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid312.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1023.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid280.5 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid328.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate597.1 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA388.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water160.8 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Allyl isothiocyanateC=CCN=C=S1385.2Standard polar33892256
Allyl isothiocyanateC=CCN=C=S854.9Standard non polar33892256
Allyl isothiocyanateC=CCN=C=S874.4Semi standard non polar33892256
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)Download (PDF)
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 ]