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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:09:57 UTC
Update Date2023-02-21 17:27:02 UTC
HMDB IDHMDB0039638
Secondary Accession Numbers
  • HMDB39638
Metabolite Identification
Common NameBrassilexin
DescriptionBrassilexin belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Brassilexin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers (Brassica oleracea var. botrytis), chinese cabbages (Brassica rapa), chinese mustards (Brassica juncea), and herbs and spices. This could make brassilexin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Brassilexin.
Structure
Data?1677000422
Synonyms
ValueSource
8H-isothiazolo(5,4-b)IndoleHMDB
BrassilexineHMDB
Chemical FormulaC9H6N2S
Average Molecular Weight174.222
Monoisotopic Molecular Weight174.025168892
IUPAC Name8H-[1,2]thiazolo[5,4-b]indole
Traditional Name8H-[1,2]thiazolo[5,4-b]indole
CAS Registry Number119752-76-0
SMILES
N1C2=C(C=NS2)C2=CC=CC=C12
InChI Identifier
InChI=1S/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,11H
InChI KeyNHMBEDDKDVIBQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct ParentIndoles
Alternative Parents
Substituents
  • Indole
  • Benzenoid
  • Heteroaromatic compound
  • Thiazole
  • Pyrrole
  • Azole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point164 - 167 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility8938 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.43ALOGPS
logP2.42ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.34 m³·mol⁻¹ChemAxon
Polarizability17.83 ųChemAxon
Number of Rings3ChemAxon
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]+134.5831661259
DarkChem[M-H]-133.06131661259
DeepCCS[M-2H]-162.78430932474
DeepCCS[M+Na]+138.24130932474
AllCCS[M+H]+134.832859911
AllCCS[M+H-H2O]+130.232859911
AllCCS[M+NH4]+139.032859911
AllCCS[M+Na]+140.332859911
AllCCS[M-H]-134.432859911
AllCCS[M+Na-2H]-134.532859911
AllCCS[M+HCOO]-134.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BrassilexinN1C2=C(C=NS2)C2=CC=CC=C122532.4Standard polar33892256
BrassilexinN1C2=C(C=NS2)C2=CC=CC=C121728.5Standard non polar33892256
BrassilexinN1C2=C(C=NS2)C2=CC=CC=C121914.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Brassilexin,1TMS,isomer #1C[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C22006.3Semi standard non polar33892256
Brassilexin,1TMS,isomer #1C[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C22013.8Standard non polar33892256
Brassilexin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C22191.8Semi standard non polar33892256
Brassilexin,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=C1SN=C22191.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Brassilexin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dj-0900000000-5d553191ff9f899717f92017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Brassilexin 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 - Brassilexin 10V, Negative-QTOFsplash10-00di-0900000000-797411d7ade8a948debd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 20V, Negative-QTOFsplash10-0002-0900000000-9ab2dd4c6e789b520d1b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 40V, Negative-QTOFsplash10-0002-0900000000-eafa615f6e5a764e75a92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 10V, Negative-QTOFsplash10-00di-0900000000-9bcf7e2f83bab5a3e2a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 20V, Negative-QTOFsplash10-00di-0900000000-9bcf7e2f83bab5a3e2a82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 40V, Negative-QTOFsplash10-00di-0900000000-3544992f5b647a14b42b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 10V, Positive-QTOFsplash10-004i-0900000000-bf8b8ee0b9b01fc0c2ec2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 20V, Positive-QTOFsplash10-004i-0900000000-be894386f7ed39d42b4d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 40V, Positive-QTOFsplash10-004j-1900000000-1a7dcfc66dbfca6644c92015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 10V, Positive-QTOFsplash10-004i-0900000000-2ca41d8f7758834ebb8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 20V, Positive-QTOFsplash10-004i-0900000000-2ca41d8f7758834ebb8f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Brassilexin 40V, Positive-QTOFsplash10-004i-0900000000-9c0501577d21d63675c82021-09-24Wishart 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+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 IDFDB019266
KNApSAcK IDC00027108
Chemspider ID19992709
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135413564
PDB IDNot Available
ChEBI ID169691
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1879001
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pedras MS, Jha M: Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation. J Org Chem. 2005 Mar 4;70(5):1828-34. [PubMed:15730307 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .