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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:36:34 UTC

Update Date

2022-03-07 02:56:49 UTC

HMDB ID

HMDB0040977

Secondary Accession Numbers

HMDB40977

Metabolite Identification

Common Name

Brassitin

Description

Brassitin 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. Brassitin has been detected, but not quantified in, brassicas and root vegetables. This could make brassitin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Brassitin.

Structure

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

  Mrv0541 02241220122D          

 15 16  0  0  0  0            999 V2000
   -0.0916    0.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    0.9118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791    0.3640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6446   -0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791   -1.0030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828   -0.2736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4563   -0.8206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -0.6383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4592    0.1816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    0.9118    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798    0.2728    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    1.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040977

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2OS/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>
GHGDPZHQDKPWOJ-UHFFFAOYSA-N

> <FORMULA>
C11H12N2OS

> <MOLECULAR_WEIGHT>
220.291

> <EXACT_MASS>
220.067033706

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.646290697193976

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.94

> <JCHEM_LOGP>
2.390543491

> <ALOGPS_LOGS>
-3.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.884973935720232

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.67210150708458

> <JCHEM_POLAR_SURFACE_AREA>
44.89

> <JCHEM_REFRACTIVITY>
62.981

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-(1H-indol-3-ylmethyl)methylsulfanylformamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      -0.171   1.020   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -1.531   1.702   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.552   0.679   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.254   0.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.937  -0.681   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.254  -1.872   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.723  -2.043   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.872  -0.681   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.341  -0.511   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.852  -1.532   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       2.213  -1.191   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.724   0.339   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.043   1.702   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       4.256   0.509   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       4.937   2.043   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0040977
HETATM    1  C1  UNL     1       5.175  -0.975   0.267  1.00  0.00           C  
HETATM    2  S1  UNL     1       4.313   0.132  -0.850  1.00  0.00           S  
HETATM    3  C2  UNL     1       2.666   0.481  -0.273  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.293  -0.063   0.816  1.00  0.00           O  
HETATM    5  N1  UNL     1       1.798   1.338  -1.002  1.00  0.00           N  
HETATM    6  C3  UNL     1       0.463   1.620  -0.542  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.346   0.376  -0.494  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.043  -0.915  -0.823  1.00  0.00           C  
HETATM    9  N2  UNL     1      -1.126  -1.699  -0.614  1.00  0.00           N  
HETATM   10  C6  UNL     1      -2.159  -0.961  -0.149  1.00  0.00           C  
HETATM   11  C7  UNL     1      -3.443  -1.320   0.200  1.00  0.00           C  
HETATM   12  C8  UNL     1      -4.300  -0.345   0.651  1.00  0.00           C  
HETATM   13  C9  UNL     1      -3.843   0.949   0.736  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.556   1.290   0.382  1.00  0.00           C  
HETATM   15  C11 UNL     1      -1.681   0.330  -0.072  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.544  -1.217   1.122  1.00  0.00           H  
HETATM   17  H2  UNL     1       6.094  -0.481   0.668  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.467  -1.894  -0.314  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.151   1.759  -1.883  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.006   2.351  -1.264  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.463   2.151   0.435  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.913  -1.256  -1.197  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.125  -2.721  -0.797  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.743  -2.356   0.112  1.00  0.00           H  
HETATM   25  H10 UNL     1      -5.298  -0.607   0.926  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.501   1.728   1.087  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.183   2.306   0.444  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
S-Methyl 1H-indole-3-ylmethylcarbamothioate, 9ci	HMDB
N-[(1H-indol-3-yl)Methyl](methylsulfanyl)carboximidate	Generator
N-[(1H-indol-3-yl)Methyl](methylsulphanyl)carboximidate	Generator
N-[(1H-indol-3-yl)Methyl](methylsulphanyl)carboximidic acid	Generator
Brassitin	MeSH

Chemical Formula

C₁₁H₁₂N₂OS

Average Molecular Weight

220.291

Monoisotopic Molecular Weight

220.067033706

IUPAC Name

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

Traditional Name

N-(1H-indol-3-ylmethyl)methylsulfanylformamide

CAS Registry Number

113866-42-5

SMILES

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

InChI Identifier

InChI=1S/C11H12N2OS/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

GHGDPZHQDKPWOJ-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
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carbonic acid derivative
Thiocarbamic acid derivative
Sulfenyl compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040977)
Cytoplasm (HMDB: HMDB0040977)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040977)

Source

Exogenous

Exogenous (HMDB: HMDB0040977)

Food

Food (HMDB: HMDB0040977)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0040977)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040977)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.054 g/L	ALOGPS
logP	1.94	ALOGPS
logP	2.39	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.67	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	44.89 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.98 m³·mol⁻¹	ChemAxon
Polarizability	23.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	149.958	31661259
DarkChem	[M-H]-	148.071	31661259
DeepCCS	[M+H]+	147.078	30932474
DeepCCS	[M-H]-	144.675	30932474
DeepCCS	[M-2H]-	180.098	30932474
DeepCCS	[M+Na]+	155.679	30932474
AllCCS	[M+H]+	147.3	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	150.4	32859911
AllCCS	[M+Na-2H]-	150.5	32859911
AllCCS	[M+HCOO]-	150.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Brassitin	CSC(=O)NCC1=CNC2=C1C=CC=C2	3453.4	Standard polar	33892256
Brassitin	CSC(=O)NCC1=CNC2=C1C=CC=C2	2285.9	Standard non polar	33892256
Brassitin	CSC(=O)NCC1=CNC2=C1C=CC=C2	2314.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Brassitin,1TMS,isomer #1	CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2273.4	Semi standard non polar	33892256
Brassitin,1TMS,isomer #1	CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C	2162.3	Standard non polar	33892256
Brassitin,1TMS,isomer #2	CSC(=O)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2259.5	Semi standard non polar	33892256
Brassitin,1TMS,isomer #2	CSC(=O)NCC1=CN([Si](C)(C)C)C2=CC=CC=C12	2111.7	Standard non polar	33892256
Brassitin,2TMS,isomer #1	CSC(=O)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2294.2	Semi standard non polar	33892256
Brassitin,2TMS,isomer #1	CSC(=O)N(CC1=CN([Si](C)(C)C)C2=CC=CC=C12)[Si](C)(C)C	2224.5	Standard non polar	33892256
Brassitin,1TBDMS,isomer #1	CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2509.9	Semi standard non polar	33892256
Brassitin,1TBDMS,isomer #1	CSC(=O)N(CC1=C[NH]C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2366.1	Standard non polar	33892256
Brassitin,1TBDMS,isomer #2	CSC(=O)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2473.1	Semi standard non polar	33892256
Brassitin,1TBDMS,isomer #2	CSC(=O)NCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12	2330.1	Standard non polar	33892256
Brassitin,2TBDMS,isomer #1	CSC(=O)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2710.2	Semi standard non polar	33892256
Brassitin,2TBDMS,isomer #1	CSC(=O)N(CC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C12)[Si](C)(C)C(C)(C)C	2657.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Brassitin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00aj-3910000000-6cc88fb2c28e0fc03b45	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassitin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Brassitin 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 - Brassitin 10V, Positive-QTOF	splash10-00di-2690000000-9fb7ce3c26fcad39aa50	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 20V, Positive-QTOF	splash10-0089-1900000000-8e5de214f75773441229	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 40V, Positive-QTOF	splash10-0f89-0900000000-d29d1a5798d1e0fae595	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 10V, Negative-QTOF	splash10-00kb-9560000000-6144076e7c8bca5fed4e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 20V, Negative-QTOF	splash10-00r2-6900000000-3a54ed6c9c9088f8bc74	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 40V, Negative-QTOF	splash10-00kf-9500000000-c554adc6517d72f13f7d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 10V, Negative-QTOF	splash10-014i-0900000000-8f00b27a61dcc0752a04	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 20V, Negative-QTOF	splash10-014j-6900000000-1842ce8eba551e0bc112	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 40V, Negative-QTOF	splash10-00kb-9700000000-3f0a235889cf3d11b456	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 10V, Positive-QTOF	splash10-000t-0900000000-61660d63784cd1d03b53	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 20V, Positive-QTOF	splash10-001i-0900000000-3690349fa0a20150ac7d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Brassitin 40V, Positive-QTOF	splash10-0fwc-5900000000-768e4bd64d07a756e5ce	2021-09-24	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

FDB020833

KNApSAcK ID

C00036838

Chemspider ID

8211978

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10036413

PDB ID

Not Available

ChEBI ID

173633

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 Brassitin (HMDB0040977)

MOL for HMDB0040977 (Brassitin)

3D MOL for HMDB0040977 (Brassitin)

3D SDF for HMDB0040977 (Brassitin)

3D-SDF for HMDB0040977 (Brassitin)

PDB for HMDB0040977 (Brassitin)

3D PDB for HMDB0040977 (Brassitin)

SMILES for HMDB0040977 (Brassitin)

INCHI for HMDB0040977 (Brassitin)

Structure for HMDB0040977 (Brassitin)

3D Structure for HMDB0040977 (Brassitin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra