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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:03:58 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033350

Secondary Accession Numbers

HMDB33350

Metabolite Identification

Common Name

Brassinin

Description

Brassinin 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. Brassinin has been detected, but not quantified in, a few different foods, such as brassicas, cauliflowers (Brassica oleracea var. botrytis), and chinese cabbages (Brassica rapa). This could make brassinin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Brassinin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241220082D          

 15 16  0  0  0  0            999 V2000
   -0.6595   -2.0199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4018   -1.6901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4838   -0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8243   -0.3703    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9072    0.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2469    0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2469    1.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    2.0199    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0713    1.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8964    1.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2262    0.5360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7307   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5766    0.7009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2262   -0.5352    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 15  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 14  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033350

> <DATABASE_NAME>
hmdb

> <SMILES>
CSC(=S)NCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2S2/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_KEY>
QYKQWFZDEDFELK-UHFFFAOYSA-N

> <FORMULA>
C11H12N2S2

> <MOLECULAR_WEIGHT>
236.356

> <EXACT_MASS>
236.044189774

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.577180947202553

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(1H-indol-3-ylmethyl)(methylsulfanyl)carbothioamide

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
3.280413075333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.013165934221902

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.483291404259634

> <JCHEM_POLAR_SURFACE_AREA>
27.82

> <JCHEM_REFRACTIVITY>
70.9719

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.99e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
brassinin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.231  -3.770   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.617  -3.155   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -2.770  -1.616   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.539  -0.691   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -1.693   0.846   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.461   1.769   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.461   3.310   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.076   3.770   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.000   2.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.540   2.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.156   1.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.231  -0.230   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.692  -0.076   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.076   1.308   0.000  0.00  0.00           C+0
HETATM   15  S   UNK     0      -4.156  -0.999   0.000  0.00  0.00           S+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   14                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    6    9   13                                                  
CONECT   15    3                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0033350
HETATM    1  C1  UNL     1       4.791   0.845  -0.412  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.757  -0.952  -0.348  1.00  0.00           S  
HETATM    3  C2  UNL     1       3.111  -1.588  -0.204  1.00  0.00           C  
HETATM    4  S2  UNL     1       2.874  -3.191  -0.131  1.00  0.00           S  
HETATM    5  N1  UNL     1       2.007  -0.687  -0.154  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.647  -1.144  -0.037  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.274   0.005  -0.009  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.013   1.341  -0.074  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.212   2.006  -0.009  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.197   1.097   0.095  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.578   1.249   0.192  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.361   0.119   0.289  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.812  -1.147   0.292  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.430  -1.295   0.195  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.649  -0.166   0.098  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.775   1.138  -0.864  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.989   1.280  -1.045  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.771   1.317   0.589  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.201   0.325  -0.203  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.557  -1.737   0.922  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.364  -1.840  -0.857  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.949   1.827  -0.162  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.351   3.034  -0.034  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.014   2.251   0.190  1.00  0.00           H  
HETATM   25  H10 UNL     1      -5.457   0.211   0.367  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.455  -2.013   0.369  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.987  -2.284   0.196  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6   19
CONECT    6    7   20   21
CONECT    7    8    8   15
CONECT    8    9   22
CONECT    9   10   23
CONECT   10   11   11   15
CONECT   11   12   24
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Brassinine	ChEBI
Methyl (1H-indol-3-ylmethyl)dithiocarbamate	ChEBI
Methyl (1H-indol-3-ylmethyl)dithiocarbamic acid	Generator
Brassinin, 1	HMDB
Carbamodithioic acid, (1H-indol-3-ylmethyl)-, methyl ester	HMDB
Methyl (1H-indol-3-ylmethyl)carbamodithioate	HMDB
Methyl (1H-indol-3-ylmethyl)carbamodithioate, 9ci	HMDB

Chemical Formula

C₁₁H₁₂N₂S₂

Average Molecular Weight

236.356

Monoisotopic Molecular Weight

236.044189774

IUPAC Name

N-(1H-indol-3-ylmethyl)(methylsulfanyl)carbothioamide

Traditional Name

brassinin

CAS Registry Number

105748-59-2

SMILES

CSC(=S)NCC1=CNC2=C1C=CC=C2

InChI Identifier

InChI=1S/C11H12N2S2/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 Key

QYKQWFZDEDFELK-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Dithiocarbamic acid ester
Pyrrole
Azacycle
Sulfenyl compound
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organosulfur compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

dithiocarbamic ester (CHEBI:38119 )
indole phytoalexin (CHEBI:38119 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033350)
Cytoplasm (HMDB: HMDB0033350)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033350)

Source

Exogenous

Food

Food (HMDB: HMDB0033350)

Vegetable

Cabbage

Chinese cabbage (FooDB: FOOD00035)
Cauliflower (FooDB: FOOD00031)

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0033350)

Not Available

Nutrient (HMDB: HMDB0033350)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 133 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	2.24	ALOGPS
logP	3.28	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.48	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	27.82 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.97 m³·mol⁻¹	ChemAxon
Polarizability	25.58 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.889	31661259
DarkChem	[M-H]-	151.029	31661259
DeepCCS	[M+H]+	149.883	30932474
DeepCCS	[M-H]-	147.315	30932474
DeepCCS	[M-2H]-	182.907	30932474
DeepCCS	[M+Na]+	158.473	30932474
AllCCS	[M+H]+	149.1	32859911
AllCCS	[M+H-H2O]+	145.3	32859911
AllCCS	[M+NH4]+	152.6	32859911
AllCCS	[M+Na]+	153.6	32859911
AllCCS	[M-H]-	151.0	32859911
AllCCS	[M+Na-2H]-	151.0	32859911
AllCCS	[M+HCOO]-	151.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brassinin	CSC(=S)NCC1=CNC2=C1C=CC=C2	3663.9	Standard polar	33892256
Brassinin	CSC(=S)NCC1=CNC2=C1C=CC=C2	2307.8	Standard non polar	33892256
Brassinin	CSC(=S)NCC1=CNC2=C1C=CC=C2	2600.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brassinin,1TMS,isomer #1	CSC(=S)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2419.3	Semi standard non polar	33892256
Brassinin,1TMS,isomer #1	CSC(=S)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2247.7	Standard non polar	33892256
Brassinin,1TMS,isomer #2	CSC(=S)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2464.6	Semi standard non polar	33892256
Brassinin,1TMS,isomer #2	CSC(=S)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2235.8	Standard non polar	33892256
Brassinin,2TMS,isomer #1	CSC(=S)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2444.4	Semi standard non polar	33892256
Brassinin,2TMS,isomer #1	CSC(=S)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2335.3	Standard non polar	33892256
Brassinin,1TBDMS,isomer #1	CSC(=S)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2661.2	Semi standard non polar	33892256
Brassinin,1TBDMS,isomer #1	CSC(=S)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2456.0	Standard non polar	33892256
Brassinin,1TBDMS,isomer #2	CSC(=S)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2649.8	Semi standard non polar	33892256
Brassinin,1TBDMS,isomer #2	CSC(=S)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2442.6	Standard non polar	33892256
Brassinin,2TBDMS,isomer #1	CSC(=S)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2854.6	Semi standard non polar	33892256
Brassinin,2TBDMS,isomer #1	CSC(=S)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2766.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brassinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-2920000000-b82fc85c71b666b10bc6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 10V, Positive-QTOF	splash10-000i-0390000000-f3d95440d3eb56cb3ca4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 20V, Positive-QTOF	splash10-001r-1940000000-3bb37b9ca2f778c0df30	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 40V, Positive-QTOF	splash10-001i-1900000000-8946cb4f82b68db4186e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 10V, Negative-QTOF	splash10-000i-3970000000-c670428db53472202f47	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 20V, Negative-QTOF	splash10-000i-2920000000-e4ec9d50bb998f68a17c	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 40V, Negative-QTOF	splash10-0a4i-9400000000-dabf3b978489bc55c31e	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 10V, Positive-QTOF	splash10-0012-0940000000-39bb845d7b7c014057a5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 20V, Positive-QTOF	splash10-001i-0900000000-2f6d68ada482fea61582	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 40V, Positive-QTOF	splash10-0f7o-8900000000-5591977ac9bd7849cb18	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 10V, Negative-QTOF	splash10-00kr-1920000000-5b5bb812be9e86966c5e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 20V, Negative-QTOF	splash10-0aor-9700000000-0a692e51b61eef05078b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassinin 40V, Negative-QTOF	splash10-0a4j-9100000000-d290e1b0e134a083b0aa	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011378

KNApSAcK ID

C00027106

Chemspider ID

2299508

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3035211

PDB ID

Not Available

ChEBI ID

38119

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Brassinin (HMDB0033350)

MOL for HMDB0033350 (Brassinin)

3D MOL for HMDB0033350 (Brassinin)

3D SDF for HMDB0033350 (Brassinin)

3D-SDF for HMDB0033350 (Brassinin)

PDB for HMDB0033350 (Brassinin)

3D PDB for HMDB0033350 (Brassinin)

SMILES for HMDB0033350 (Brassinin)

INCHI for HMDB0033350 (Brassinin)

Structure for HMDB0033350 (Brassinin)

3D Structure for HMDB0033350 (Brassinin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra