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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:22:33 UTC

Update Date

2022-03-07 02:56:44 UTC

HMDB ID

HMDB0040790

Secondary Accession Numbers

HMDB40790

Metabolite Identification

Common Name

4-Methoxybrassinin

Description

4-Methoxybrassinin 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. 4-Methoxybrassinin has been detected, but not quantified in, brassicas. This could make 4-methoxybrassinin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Methoxybrassinin.

Structure

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

HMDB0040790
     RDKit          3D
4-Methoxybrassinin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3804    3.0682    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520    1.8742    0.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.6073    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    0.4202    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0331   -0.8751    0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614   -1.9243    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.7527    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.5807    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -1.8785   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -0.5588    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735    0.5980    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    0.2397   -0.0151 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.2460   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    2.8088    0.0111 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210    0.8280   -0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -0.9850   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -0.4556    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    3.8567    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    3.3998   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    3.0162    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2210    1.2650    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1114   -1.0931    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9504    0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -3.6199   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254   -2.3308   -0.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    1.2616    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066    1.2463   -0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906   -0.7460   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3360   -1.2554   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411   -1.3707    0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.3591   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17  3  1  0
 17  7  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
M  END


  Mrv0541 02241218232D          

 17 18  0  0  0  0            999 V2000
   -0.6596   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -1.6909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -0.5359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -0.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    1.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    2.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    0.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971    1.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -1.4433    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0040790

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=CC2=C1C(CNC(=S)SC)=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2OS2/c1-15-10-5-3-4-9-11(10)8(6-13-9)7-14-12(16)17-2/h3-6,13H,7H2,1-2H3,(H,14,16)

> <INCHI_KEY>
JVKOHVNWMQYCIN-UHFFFAOYSA-N

> <FORMULA>
C12H14N2OS2

> <MOLECULAR_WEIGHT>
266.382

> <EXACT_MASS>
266.05475446

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.026190560942695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.1227418096666666

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.243797278858878

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.487158851251522

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857500229977964

> <JCHEM_POLAR_SURFACE_AREA>
37.05

> <JCHEM_REFRACTIVITY>
77.4351

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(4-methoxy-1H-indol-3-yl)methyl]methylsulfanylcarbothioamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0040790
     RDKit          3D
4-Methoxybrassinin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3804    3.0682    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520    1.8742    0.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.6073    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    0.4202    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0331   -0.8751    0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614   -1.9243    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.7527    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.5807    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -1.8785   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -0.5588    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735    0.5980    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    0.2397   -0.0151 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.2460   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    2.8088    0.0111 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210    0.8280   -0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -0.9850   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -0.4556    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    3.8567    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    3.3998   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    3.0162    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2210    1.2650    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1114   -1.0931    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9504    0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -3.6199   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254   -2.3308   -0.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    1.2616    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066    1.2463   -0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906   -0.7460   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3360   -1.2554   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411   -1.3707    0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.3591   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17  3  1  0
 17  7  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
M  END

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  -3.772   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.617  -3.156   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -2.771  -1.616   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -4.157  -1.000   0.000  0.00  0.00           S+0
HETATM    5  N   UNK     0      -1.539  -0.692   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.693   0.846   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.461   1.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.461   3.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.077   3.772   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.001   2.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.077   1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.693  -0.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.233  -0.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.157   1.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.541   2.386   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.923  -1.462   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.693  -2.694   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11    7   10   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   12   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0040790
HETATM    1  C1  UNL     1      -2.380   3.068   0.125  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.652   1.874   0.093  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.195   0.607   0.086  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.554   0.420   0.112  1.00  0.00           C  
HETATM    5  C4  UNL     1      -4.033  -0.875   0.103  1.00  0.00           C  
HETATM    6  C5  UNL     1      -3.161  -1.924   0.070  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.785  -1.753   0.043  1.00  0.00           C  
HETATM    8  N1  UNL     1      -0.734  -2.581   0.009  1.00  0.00           N  
HETATM    9  C7  UNL     1       0.438  -1.878  -0.005  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.073  -0.559   0.022  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.974   0.598   0.019  1.00  0.00           C  
HETATM   12  N2  UNL     1       2.375   0.240  -0.015  1.00  0.00           N  
HETATM   13  C10 UNL     1       3.373   1.246  -0.021  1.00  0.00           C  
HETATM   14  S1  UNL     1       2.901   2.809   0.011  1.00  0.00           S  
HETATM   15  S2  UNL     1       5.121   0.828  -0.064  1.00  0.00           S  
HETATM   16  C11 UNL     1       5.266  -0.985  -0.094  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.301  -0.456   0.052  1.00  0.00           C  
HETATM   18  H1  UNL     1      -1.709   3.857   0.571  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.510   3.400  -0.943  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.322   3.016   0.673  1.00  0.00           H  
HETATM   21  H4  UNL     1      -4.221   1.265   0.138  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.111  -1.093   0.123  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.517  -2.950   0.062  1.00  0.00           H  
HETATM   24  H7  UNL     1      -0.814  -3.620  -0.004  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.425  -2.331  -0.032  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.840   1.262   0.896  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.707   1.246  -0.868  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.691  -0.746  -0.036  1.00  0.00           H  
HETATM   29  H12 UNL     1       6.336  -1.255  -0.195  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.841  -1.371   0.864  1.00  0.00           H  
HETATM   31  H14 UNL     1       4.641  -1.359  -0.930  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   21
CONECT    5    6    6   22
CONECT    6    7   23
CONECT    7    8   17   17
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11   17
CONECT   11   12   26   27
CONECT   12   13   28
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   29   30   31
END

HMDB0040790
     RDKit          3D
4-Methoxybrassinin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.3804    3.0682    0.1253 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6520    1.8742    0.0929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1950    0.6073    0.0860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5542    0.4202    0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0331   -0.8751    0.1032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1614   -1.9243    0.0698 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7853   -1.7527    0.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7342   -2.5807    0.0095 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -1.8785   -0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0732   -0.5588    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9735    0.5980    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3747    0.2397   -0.0151 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3732    1.2460   -0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9009    2.8088    0.0111 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1210    0.8280   -0.0642 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.2656   -0.9850   -0.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3011   -0.4556    0.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7087    3.8567    0.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5101    3.3998   -0.9426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3223    3.0162    0.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2210    1.2650    0.1379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1114   -1.0931    0.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169   -2.9504    0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8137   -3.6199   -0.0039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4254   -2.3308   -0.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8400    1.2616    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7066    1.2463   -0.8677 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6906   -0.7460   -0.0361 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3360   -1.2554   -0.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8411   -1.3707    0.8636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6414   -1.3591   -0.9297 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10 17  1  0
 17  3  1  0
 17  7  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-(1H-Indazol-5-ylazo)-N-methyl-benzenamine	HMDB
5-(4-methylaminophenylazo)Indazole	HMDB
Ma5i	HMDB
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carboimidothioate	Generator
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboimidothioate	Generator
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboimidothioic acid	Generator

Chemical Formula

C₁₂H₁₄N₂OS₂

Average Molecular Weight

266.382

Monoisotopic Molecular Weight

266.05475446

IUPAC Name

N-[(4-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide

Traditional Name

N-[(4-methoxy-1H-indol-3-yl)methyl]methylsulfanylcarbothioamide

CAS Registry Number

129602-03-5

SMILES

COC1=CC=CC2=C1C(CNC(=S)SC)=CN2

InChI Identifier

InChI=1S/C12H14N2OS2/c1-15-10-5-3-4-9-11(10)8(6-13-9)7-14-12(16)17-2/h3-6,13H,7H2,1-2H3,(H,14,16)

InChI Key

JVKOHVNWMQYCIN-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
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Dithiocarbamic acid ester
Ether
Sulfenyl compound
Azacycle
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0040790)
Cytoplasm (HMDB: HMDB0040790)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0040790)

Source

Exogenous

Exogenous (HMDB: HMDB0040790)

Food

Food (HMDB: HMDB0040790)

Vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0040790)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0040790)

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	1507 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0066 g/L	ALOGPS
logP	2.43	ALOGPS
logP	3.12	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.44 m³·mol⁻¹	ChemAxon
Polarizability	28.03 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]+	159.727	31661259
DarkChem	[M-H]-	156.074	31661259
DeepCCS	[M+H]+	160.01	30932474
DeepCCS	[M-H]-	157.652	30932474
DeepCCS	[M-2H]-	191.411	30932474
DeepCCS	[M+Na]+	166.47	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.0	32859911
AllCCS	[M-H]-	158.9	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	159.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.69 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0407 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.73 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2563.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	507.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	179.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	308.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	390.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	642.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	822.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	218.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1389.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	487.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1510.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	545.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	497.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	484.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	515.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	54.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Methoxybrassinin	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2	3916.7	Standard polar	33892256
4-Methoxybrassinin	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2	2478.7	Standard non polar	33892256
4-Methoxybrassinin	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2	2831.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Methoxybrassinin,1TMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C)=C[NH]2	2584.1	Semi standard non polar	33892256
4-Methoxybrassinin,1TMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C)=C[NH]2	2452.4	Standard non polar	33892256
4-Methoxybrassinin,1TMS,isomer #2	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2[Si](C)(C)C	2676.6	Semi standard non polar	33892256
4-Methoxybrassinin,1TMS,isomer #2	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2[Si](C)(C)C	2417.5	Standard non polar	33892256
4-Methoxybrassinin,2TMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C)=CN2[Si](C)(C)C	2624.2	Semi standard non polar	33892256
4-Methoxybrassinin,2TMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C)=CN2[Si](C)(C)C	2507.1	Standard non polar	33892256
4-Methoxybrassinin,1TBDMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)=C[NH]2	2825.4	Semi standard non polar	33892256
4-Methoxybrassinin,1TBDMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)=C[NH]2	2665.4	Standard non polar	33892256
4-Methoxybrassinin,1TBDMS,isomer #2	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2[Si](C)(C)C(C)(C)C	2865.0	Semi standard non polar	33892256
4-Methoxybrassinin,1TBDMS,isomer #2	COC1=CC=CC2=C1C(CNC(=S)SC)=CN2[Si](C)(C)C(C)(C)C	2624.5	Standard non polar	33892256
4-Methoxybrassinin,2TBDMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	3063.1	Semi standard non polar	33892256
4-Methoxybrassinin,2TBDMS,isomer #1	COC1=CC=CC2=C1C(CN(C(=S)SC)[Si](C)(C)C(C)(C)C)=CN2[Si](C)(C)C(C)(C)C	2906.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxybrassinin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0wt9-5890000000-b6a691c3d521d3e8feb4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxybrassinin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Methoxybrassinin 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 - 4-Methoxybrassinin 10V, Positive-QTOF	splash10-014i-1490000000-dc13cd816675cef5b853	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 20V, Positive-QTOF	splash10-03xr-2940000000-cedbd2b589dbd5876cff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 40V, Positive-QTOF	splash10-0j5c-1900000000-06206fc66b89e6a11bc8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 10V, Negative-QTOF	splash10-014i-1090000000-c0c501f38935df712f3a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 20V, Negative-QTOF	splash10-014j-3690000000-bd47e285a3789a75d08f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 40V, Negative-QTOF	splash10-052b-9610000000-ac6938f8ba0abc9acb20	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 10V, Negative-QTOF	splash10-066r-5790000000-f93bcff702aec9024d57	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 20V, Negative-QTOF	splash10-053r-3900000000-3edf0dcf7fc5d49f54b5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 40V, Negative-QTOF	splash10-0a4i-9610000000-a50778711b92b4df3408	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 10V, Positive-QTOF	splash10-014i-0290000000-034ddc1f6877fba6dc53	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 20V, Positive-QTOF	splash10-03xr-0920000000-ddce98a5773954714bfc	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Methoxybrassinin 40V, Positive-QTOF	splash10-0ab9-9600000000-3c5df4f17bc9a80ebb5a	2021-09-25	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

FDB020606

KNApSAcK ID

C00036583

Chemspider ID

9186134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11010948

PDB ID

Not Available

ChEBI ID

169342

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1886421

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 4-Methoxybrassinin (HMDB0040790)

MOL for HMDB0040790 (4-Methoxybrassinin)

3D MOL for HMDB0040790 (4-Methoxybrassinin)

3D SDF for HMDB0040790 (4-Methoxybrassinin)

3D-SDF for HMDB0040790 (4-Methoxybrassinin)

PDB for HMDB0040790 (4-Methoxybrassinin)

3D PDB for HMDB0040790 (4-Methoxybrassinin)

SMILES for HMDB0040790 (4-Methoxybrassinin)

INCHI for HMDB0040790 (4-Methoxybrassinin)

Structure for HMDB0040790 (4-Methoxybrassinin)

3D Structure for HMDB0040790 (4-Methoxybrassinin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra