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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:04:01 UTC
Update Date2022-03-07 02:53:40 UTC
HMDB IDHMDB0033351
Secondary Accession Numbers
  • HMDB33351
Metabolite Identification
Common NameMethoxybrassinin
DescriptionMethoxybrassinin 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. Methoxybrassinin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers (Brassica oleracea var. botrytis), chinese cabbages (Brassica rapa), swedes (Brassica napus), and turnips (Brassica rapa var. rapa). This could make methoxybrassinin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Methoxybrassinin.
Structure
Data?1563862392
SynonymsNot Available
Chemical FormulaC12H14N2OS2
Average Molecular Weight266.382
Monoisotopic Molecular Weight266.05475446
IUPAC NameN-[(1-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide
Traditional NameN-[(1-methoxyindol-3-yl)methyl]methylsulfanylcarbothioamide
CAS Registry Number105748-60-5
SMILES
CON1C=C(CNC(=S)SC)C2=C1C=CC=C2
InChI Identifier
InChI=1S/C12H14N2OS2/c1-15-14-8-9(7-13-12(16)17-2)10-5-3-4-6-11(10)14/h3-6,8H,7H2,1-2H3,(H,13,16)
InChI KeyKFZBENSULWNJKD-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
  • Dithiocarbamic acid ester
  • Heteroaromatic compound
  • Sulfenyl compound
  • Azacycle
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organosulfur compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 Solubility0.027 g/LALOGPS
logP2.61ALOGPS
logP2.99ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)7.49ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area26.19 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.63 m³·mol⁻¹ChemAxon
Polarizability28.61 ųChemAxon
Number of Rings2ChemAxon
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]+160.85331661259
DarkChem[M-H]-157.34931661259
DeepCCS[M+H]+151.99830932474
DeepCCS[M-H]-149.6430932474
DeepCCS[M-2H]-183.49230932474
DeepCCS[M+Na]+158.32330932474
AllCCS[M+H]+156.732859911
AllCCS[M+H-H2O]+153.132859911
AllCCS[M+NH4]+160.032859911
AllCCS[M+Na]+161.032859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-158.732859911
AllCCS[M+HCOO]-158.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MethoxybrassininCON1C=C(CNC(=S)SC)C2=C1C=CC=C23885.5Standard polar33892256
MethoxybrassininCON1C=C(CNC(=S)SC)C2=C1C=CC=C22299.2Standard non polar33892256
MethoxybrassininCON1C=C(CNC(=S)SC)C2=C1C=CC=C22584.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Methoxybrassinin,1TMS,isomer #1CON1C=C(CN(C(=S)SC)[Si](C)(C)C)C2=CC=CC=C212431.9Semi standard non polar33892256
Methoxybrassinin,1TMS,isomer #1CON1C=C(CN(C(=S)SC)[Si](C)(C)C)C2=CC=CC=C212372.4Standard non polar33892256
Methoxybrassinin,1TBDMS,isomer #1CON1C=C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)C2=CC=CC=C212651.6Semi standard non polar33892256
Methoxybrassinin,1TBDMS,isomer #1CON1C=C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)C2=CC=CC=C212581.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Methoxybrassinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-1590000000-d7dbcf70d6ccf90ce3f42017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxybrassinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Methoxybrassinin 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 - Methoxybrassinin 10V, Positive-QTOFsplash10-014i-1490000000-4f8d5146199738d35d6e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 20V, Positive-QTOFsplash10-00or-1940000000-95c43507f2b0e6c33b0b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 40V, Positive-QTOFsplash10-002g-2900000000-c5da380421abf0cbd46f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 10V, Negative-QTOFsplash10-014i-3190000000-f33c19225e13fa9646e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 20V, Negative-QTOFsplash10-000i-1940000000-109ed46c8252053f77972016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 40V, Negative-QTOFsplash10-00n4-9710000000-fd441621bd211ae1fc1a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 10V, Positive-QTOFsplash10-014i-0290000000-b495fb7284a234a90da52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 20V, Positive-QTOFsplash10-014i-0790000000-94c0d5515759531d48fa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 40V, Positive-QTOFsplash10-053s-3900000000-dbfc68edcdac0d7f1ec42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 10V, Negative-QTOFsplash10-00kr-1940000000-4ced507f74157d770dde2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 20V, Negative-QTOFsplash10-0aor-9710000000-a69833b803b9cedf489a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Methoxybrassinin 40V, Negative-QTOFsplash10-0a4i-9510000000-fafdda5a6048bfb496022021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB011379
KNApSAcK IDC00001546
Chemspider ID2301195
KEGG Compound IDC08506
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound3037463
PDB IDNot Available
ChEBI ID6841
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.. .