Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:58:03 UTC
Update Date2022-03-07 02:55:51 UTC
HMDB IDHMDB0038634
Secondary Accession Numbers
  • HMDB38634
Metabolite Identification
Common Name(-)-Dioxibrassinin
Description(-)-Dioxibrassinin belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom (-)-Dioxibrassinin has been detected, but not quantified in, brassicas and cauliflowers (Brassica oleracea var. botrytis). This could make (-)-dioxibrassinin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (-)-Dioxibrassinin.
Structure
Data?1563863231
Synonyms
ValueSource
DioxibrassininHMDB
N-[(2,3-Dihydroxy-3H-indol-3-yl)methyl](methylsulfanyl)carboimidothioateGenerator
N-[(2,3-Dihydroxy-3H-indol-3-yl)methyl](methylsulphanyl)carboimidothioateGenerator
N-[(2,3-Dihydroxy-3H-indol-3-yl)methyl](methylsulphanyl)carboimidothioic acidGenerator
Chemical FormulaC11H12N2O2S2
Average Molecular Weight268.355
Monoisotopic Molecular Weight268.034019018
IUPAC NameN-[(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide
Traditional NameN-[(3-hydroxy-2-oxo-1H-indol-3-yl)methyl]methylsulfanylcarbothioamide
CAS Registry Number133761-64-5
SMILES
CSC(=S)NCC1(O)C(=O)NC2=C1C=CC=C2
InChI Identifier
InChI=1S/C11H12N2O2S2/c1-17-10(16)12-6-11(15)7-4-2-3-5-8(7)13-9(11)14/h2-5,15H,6H2,1H3,(H,12,16)(H,13,14)
InChI KeyDXLDPLVGKCAHPY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentBeta amino acids and derivatives
Alternative Parents
Substituents
  • Beta amino acid or derivatives
  • Indole or derivatives
  • Dihydroindole
  • Benzenoid
  • Tertiary alcohol
  • Dithiocarbamic acid ester
  • Carboxamide group
  • Lactam
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic oxide
  • Carbonyl group
  • Organic nitrogen compound
  • 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 Solubility6996 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.063 g/LALOGPS
logP0.95ALOGPS
logP1.72ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.5ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area61.36 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity74.19 m³·mol⁻¹ChemAxon
Polarizability27.13 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]+161.80931661259
DarkChem[M-H]-156.26331661259
DeepCCS[M+H]+160.09130932474
DeepCCS[M-H]-157.73330932474
DeepCCS[M-2H]-190.61830932474
DeepCCS[M+Na]+166.18430932474
AllCCS[M+H]+156.532859911
AllCCS[M+H-H2O]+153.032859911
AllCCS[M+NH4]+159.732859911
AllCCS[M+Na]+160.732859911
AllCCS[M-H]-158.632859911
AllCCS[M+Na-2H]-158.732859911
AllCCS[M+HCOO]-159.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(-)-DioxibrassininCSC(=S)NCC1(O)C(=O)NC2=C1C=CC=C24237.4Standard polar33892256
(-)-DioxibrassininCSC(=S)NCC1(O)C(=O)NC2=C1C=CC=C22439.2Standard non polar33892256
(-)-DioxibrassininCSC(=S)NCC1(O)C(=O)NC2=C1C=CC=C22735.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(-)-Dioxibrassinin,1TMS,isomer #1CSC(=S)NCC1(O[Si](C)(C)C)C(=O)NC2=CC=CC=C212576.6Semi standard non polar33892256
(-)-Dioxibrassinin,1TMS,isomer #2CSC(=S)N(CC1(O)C(=O)NC2=CC=CC=C21)[Si](C)(C)C2530.2Semi standard non polar33892256
(-)-Dioxibrassinin,1TMS,isomer #3CSC(=S)NCC1(O)C(=O)N([Si](C)(C)C)C2=CC=CC=C212503.6Semi standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C)C(=O)NC2=CC=CC=C21)[Si](C)(C)C2543.4Semi standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C)C(=O)NC2=CC=CC=C21)[Si](C)(C)C2426.5Standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #2CSC(=S)NCC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C212512.2Semi standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #2CSC(=S)NCC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C212308.7Standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #3CSC(=S)N(CC1(O)C(=O)N([Si](C)(C)C)C2=CC=CC=C21)[Si](C)(C)C2467.2Semi standard non polar33892256
(-)-Dioxibrassinin,2TMS,isomer #3CSC(=S)N(CC1(O)C(=O)N([Si](C)(C)C)C2=CC=CC=C21)[Si](C)(C)C2404.0Standard non polar33892256
(-)-Dioxibrassinin,3TMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C21)[Si](C)(C)C2509.8Semi standard non polar33892256
(-)-Dioxibrassinin,3TMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C)C(=O)N([Si](C)(C)C)C2=CC=CC=C21)[Si](C)(C)C2451.3Standard non polar33892256
(-)-Dioxibrassinin,1TBDMS,isomer #1CSC(=S)NCC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=CC=C212799.1Semi standard non polar33892256
(-)-Dioxibrassinin,1TBDMS,isomer #2CSC(=S)N(CC1(O)C(=O)NC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2762.4Semi standard non polar33892256
(-)-Dioxibrassinin,1TBDMS,isomer #3CSC(=S)NCC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C212750.2Semi standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2968.5Semi standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C(C)(C)C)C(=O)NC2=CC=CC=C21)[Si](C)(C)C(C)(C)C2872.0Standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #2CSC(=S)NCC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C212919.2Semi standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #2CSC(=S)NCC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C212757.7Standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #3CSC(=S)N(CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2944.5Semi standard non polar33892256
(-)-Dioxibrassinin,2TBDMS,isomer #3CSC(=S)N(CC1(O)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C2834.6Standard non polar33892256
(-)-Dioxibrassinin,3TBDMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3129.7Semi standard non polar33892256
(-)-Dioxibrassinin,3TBDMS,isomer #1CSC(=S)N(CC1(O[Si](C)(C)C(C)(C)C)C(=O)N([Si](C)(C)C(C)(C)C)C2=CC=CC=C21)[Si](C)(C)C(C)(C)C3063.1Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Dioxibrassinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-00xs-4920000000-a5f063a35aef4786117e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Dioxibrassinin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-5191000000-f2c3cefa052e8100f94d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (-)-Dioxibrassinin 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 - (-)-Dioxibrassinin 10V, Positive-QTOFsplash10-014i-1590000000-e78bec86dcf343acc64c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 20V, Positive-QTOFsplash10-004i-1930000000-0ecb55d2ec13fef6d2ab2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 40V, Positive-QTOFsplash10-07l6-4900000000-25f2be0639ba6b9e147a2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 10V, Negative-QTOFsplash10-014i-4290000000-42299a002f8efeb41dd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 20V, Negative-QTOFsplash10-014m-9780000000-bc1c5f3cf05d8fca6f8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 40V, Negative-QTOFsplash10-052f-9300000000-4f3a90c1e6f1fa25f5f62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 10V, Positive-QTOFsplash10-014i-0090000000-fc264598587d2b8ae50c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 20V, Positive-QTOFsplash10-01di-0790000000-6cb964256e4bbe3b43552021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 40V, Positive-QTOFsplash10-009g-7910000000-0fec0c7df407beca0ee22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 10V, Negative-QTOFsplash10-014i-0090000000-bcc6d510502be955bfaf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 20V, Negative-QTOFsplash10-014j-3970000000-1b9c697cfb245ff8367d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (-)-Dioxibrassinin 40V, Negative-QTOFsplash10-0007-9320000000-d2ce65cb5b35363c35662021-09-24Wishart 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 IDFDB018029
KNApSAcK IDC00037061
Chemspider ID9982363
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11807698
PDB IDNot Available
ChEBI ID173897
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1870031
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.. .