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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:36:34 UTC
Update Date2022-03-07 02:56:49 UTC
HMDB IDHMDB0040977
Secondary Accession Numbers
  • HMDB40977
Metabolite Identification
Common NameBrassitin
DescriptionBrassitin belongs to the class of organic compounds known as 3-alkylindoles. 3-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Brassitin has been detected, but not quantified in, brassicas and root vegetables. This could make brassitin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Brassitin.
Structure
Data?1563863610
Synonyms
ValueSource
S-Methyl 1H-indole-3-ylmethylcarbamothioate, 9ciHMDB
N-[(1H-indol-3-yl)Methyl](methylsulfanyl)carboximidateGenerator
N-[(1H-indol-3-yl)Methyl](methylsulphanyl)carboximidateGenerator
N-[(1H-indol-3-yl)Methyl](methylsulphanyl)carboximidic acidGenerator
BrassitinMeSH
Chemical FormulaC11H12N2OS
Average Molecular Weight220.291
Monoisotopic Molecular Weight220.067033706
IUPAC NameN-(1H-indol-3-ylmethyl)(methylsulfanyl)formamide
Traditional NameN-(1H-indol-3-ylmethyl)methylsulfanylformamide
CAS Registry Number113866-42-5
SMILES
CSC(=O)NCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H12N2OS/c1-15-11(14)13-7-8-6-12-10-5-3-2-4-9(8)10/h2-6,12H,7H2,1H3,(H,13,14)
InChI KeyGHGDPZHQDKPWOJ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Thiocarbamic acid derivative
  • Sulfenyl compound
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
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
Water Solubility0.054 g/LALOGPS
logP1.94ALOGPS
logP2.39ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)15.67ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area44.89 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity62.98 m³·mol⁻¹ChemAxon
Polarizability23.65 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.95831661259
DarkChem[M-H]-148.07131661259
DeepCCS[M+H]+147.07830932474
DeepCCS[M-H]-144.67530932474
DeepCCS[M-2H]-180.09830932474
DeepCCS[M+Na]+155.67930932474
AllCCS[M+H]+147.332859911
AllCCS[M+H-H2O]+143.332859911
AllCCS[M+NH4]+150.932859911
AllCCS[M+Na]+152.032859911
AllCCS[M-H]-150.432859911
AllCCS[M+Na-2H]-150.532859911
AllCCS[M+HCOO]-150.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BrassitinCSC(=O)NCC1=CNC2=C1C=CC=C23453.4Standard polar33892256
BrassitinCSC(=O)NCC1=CNC2=C1C=CC=C22285.9Standard non polar33892256
BrassitinCSC(=O)NCC1=CNC2=C1C=CC=C22314.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Brassitin,1TMS,isomer #1CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2273.4Semi standard non polar33892256
Brassitin,1TMS,isomer #1CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C2162.3Standard non polar33892256
Brassitin,1TMS,isomer #2CSC(=O)NCC1=CN([Si](C)(C)C)C2=CC=CC=C122259.5Semi standard non polar33892256
Brassitin,1TMS,isomer #2CSC(=O)NCC1=CN([Si](C)(C)C)C2=CC=CC=C122111.7Standard non polar33892256
Brassitin,2TMS,isomer #1CSC(=O)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2294.2Semi standard non polar33892256
Brassitin,2TMS,isomer #1CSC(=O)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C2224.5Standard non polar33892256
Brassitin,1TBDMS,isomer #1CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2509.9Semi standard non polar33892256
Brassitin,1TBDMS,isomer #1CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2366.1Standard non polar33892256
Brassitin,1TBDMS,isomer #2CSC(=O)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122473.1Semi standard non polar33892256
Brassitin,1TBDMS,isomer #2CSC(=O)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122330.1Standard non polar33892256
Brassitin,2TBDMS,isomer #1CSC(=O)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2710.2Semi standard non polar33892256
Brassitin,2TBDMS,isomer #1CSC(=O)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C2657.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brassitin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00aj-3910000000-6cc88fb2c28e0fc03b452017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brassitin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brassitin 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 - Brassitin 10V, Positive-QTOFsplash10-00di-2690000000-9fb7ce3c26fcad39aa502017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 20V, Positive-QTOFsplash10-0089-1900000000-8e5de214f757734412292017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 40V, Positive-QTOFsplash10-0f89-0900000000-d29d1a5798d1e0fae5952017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 10V, Negative-QTOFsplash10-00kb-9560000000-6144076e7c8bca5fed4e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 20V, Negative-QTOFsplash10-00r2-6900000000-3a54ed6c9c9088f8bc742017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 40V, Negative-QTOFsplash10-00kf-9500000000-c554adc6517d72f13f7d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 10V, Negative-QTOFsplash10-014i-0900000000-8f00b27a61dcc0752a042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 20V, Negative-QTOFsplash10-014j-6900000000-1842ce8eba551e0bc1122021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 40V, Negative-QTOFsplash10-00kb-9700000000-3f0a235889cf3d11b4562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 10V, Positive-QTOFsplash10-000t-0900000000-61660d63784cd1d03b532021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 20V, Positive-QTOFsplash10-001i-0900000000-3690349fa0a20150ac7d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassitin 40V, Positive-QTOFsplash10-0fwc-5900000000-768e4bd64d07a756e5ce2021-09-24Wishart 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 IDFDB020833
KNApSAcK IDC00036838
Chemspider ID8211978
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10036413
PDB IDNot Available
ChEBI ID173633
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .