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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:42:20 UTC
Update Date2022-03-07 02:56:52 UTC
HMDB IDHMDB0041060
Secondary Accession Numbers
  • HMDB41060
Metabolite Identification
Common NameDehydro-4-methoxycyclobrassinin
DescriptionDehydro-4-methoxycyclobrassinin 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. Dehydro-4-methoxycyclobrassinin has been detected, but not quantified in, brassicas and root vegetables. This could make dehydro-4-methoxycyclobrassinin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Dehydro-4-methoxycyclobrassinin.
Structure
Data?1563863619
Synonyms
ValueSource
5-Methoxy-2-(methylsulphanyl)-[1,3]thiazino[6,5-b]indoleHMDB
Chemical FormulaC12H10N2OS2
Average Molecular Weight262.351
Monoisotopic Molecular Weight262.023454332
IUPAC Name5-methoxy-2-(methylsulfanyl)-[1,3]thiazino[6,5-b]indole
Traditional Name5-methoxy-2-(methylsulfanyl)-[1,3]thiazino[6,5-b]indole
CAS Registry Number154933-74-1
SMILES
COC1=CC=CC2=C1C1=CN=C(SC)SC1=N2
InChI Identifier
InChI=1S/C12H10N2OS2/c1-15-9-5-3-4-8-10(9)7-6-13-12(16-2)17-11(7)14-8/h3-6H,1-2H3
InChI KeyJDYSKRAQSOYTDY-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
  • Aryl thioether
  • Anisole
  • Alkyl aryl ether
  • Alkylarylthioether
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Ether
  • Azacycle
  • Sulfenyl compound
  • Thioether
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxygen 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 Point142 - 143 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.073 g/LALOGPS
logP2.49ALOGPS
logP3.41ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)3.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area35.01 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity70.07 m³·mol⁻¹ChemAxon
Polarizability27.35 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+156.17131661259
DarkChem[M-H]-158.86331661259
DeepCCS[M+H]+148.49230932474
DeepCCS[M-H]-146.13430932474
DeepCCS[M-2H]-180.55930932474
DeepCCS[M+Na]+155.4630932474
AllCCS[M+H]+155.632859911
AllCCS[M+H-H2O]+151.932859911
AllCCS[M+NH4]+159.032859911
AllCCS[M+Na]+160.032859911
AllCCS[M-H]-158.132859911
AllCCS[M+Na-2H]-157.732859911
AllCCS[M+HCOO]-157.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Dehydro-4-methoxycyclobrassininCOC1=CC=CC2=C1C1=CN=C(SC)SC1=N23416.3Standard polar33892256
Dehydro-4-methoxycyclobrassininCOC1=CC=CC2=C1C1=CN=C(SC)SC1=N22457.4Standard non polar33892256
Dehydro-4-methoxycyclobrassininCOC1=CC=CC2=C1C1=CN=C(SC)SC1=N22537.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Dehydro-4-methoxycyclobrassinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-006t-1960000000-0a0ae368d89cb56042362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dehydro-4-methoxycyclobrassinin 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 - Dehydro-4-methoxycyclobrassinin 10V, Positive-QTOFsplash10-03di-1190000000-4ff2d12de800d5cc38f52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 20V, Positive-QTOFsplash10-03xr-1090000000-170ac3a6c0603a80f54f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 40V, Positive-QTOFsplash10-00ba-2910000000-461aaa000d3cba7ef8352017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 10V, Negative-QTOFsplash10-03xs-2090000000-2af6405a4f7705ed86002017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 20V, Negative-QTOFsplash10-01ba-9080000000-b317696a19613bb4f6302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 40V, Negative-QTOFsplash10-0a4i-9320000000-0e9c65965ca3b10e920e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 10V, Negative-QTOFsplash10-03di-0090000000-ebeed3751c7ccd8b58a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 20V, Negative-QTOFsplash10-03di-0090000000-ebeed3751c7ccd8b58a22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 40V, Negative-QTOFsplash10-0bti-0980000000-38d9f889fdb0ec3159d62021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 10V, Positive-QTOFsplash10-03di-0090000000-b5d742068d8cb3630b7e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 20V, Positive-QTOFsplash10-03di-0090000000-b5d742068d8cb3630b7e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dehydro-4-methoxycyclobrassinin 40V, Positive-QTOFsplash10-05o0-0290000000-9c7c393b110f6b233b4b2021-09-22Wishart 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 IDFDB020934
KNApSAcK IDC00055332
Chemspider ID8508391
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10332932
PDB IDNot Available
ChEBI ID169362
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.. .