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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:42:16 UTC

Update Date

2022-03-07 02:56:52 UTC

HMDB ID

HMDB0041059

Secondary Accession Numbers

HMDB41059

Metabolite Identification

Common Name

N-Methoxyspirobrassinol methyl ether

Description

N-Methoxyspirobrassinol methyl ether belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. N-Methoxyspirobrassinol methyl ether has been detected, but not quantified in, brassicas and radishes (Raphanus sativus). This could make N-methoxyspirobrassinol methyl ether a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on N-Methoxyspirobrassinol methyl ether.

Structure

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

HMDB0041059
     RDKit          3D
N-Methoxyspirobrassinol methyl ether
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.5440   -2.9794    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.1776    0.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -0.8213    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -0.1124   -0.5632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.5236   -1.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.0269   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    1.1412   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411    2.2877   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    3.4070   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    3.3498   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    2.2268   -0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    1.0852   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -0.2258    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.1044   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -0.9936    0.0805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -0.5373    1.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -0.2936    2.0638 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261   -0.8191    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -0.1227    1.9272 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -2.7264    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557   -4.0267    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.9312    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -0.6346    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8332   -0.8458   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9169    0.6568    0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.5882   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    2.3345   -1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    4.3115   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    4.2157   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795    2.1541    0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401   -0.9383   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -2.1601   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398   -1.7472    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141   -0.9929    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0177    0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 13  3  1  0
 12  7  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
M  END


  Mrv0541 05061312212D          

 19 21  0  0  0  0            999 V2000
    0.4864    5.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097    4.9341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5453    1.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9011    1.8017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4077    2.4529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    1.9148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0970    3.2172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9703    2.1351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7732    2.6791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798    3.3303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245    3.7842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850    2.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9974    2.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1778    1.9060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8170    4.0133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3733    4.2908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0976    4.7891    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096    2.6161    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216    3.2402    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16  1  1  0  0  0  0
 16 11  1  0  0  0  0
 17  2  1  0  0  0  0
 17 15  1  0  0  0  0
 18  3  1  0  0  0  0
 18 12  1  0  0  0  0
 19 12  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041059

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1N(OC)C2=CC=CC=C2C11CN=C(SC)S1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O2S2/c1-16-11-13(8-14-12(18-3)19-13)9-6-4-5-7-10(9)15(11)17-2/h4-7,11H,8H2,1-3H3

> <INCHI_KEY>
KJSKSCBVIGFOKZ-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O2S2

> <MOLECULAR_WEIGHT>
296.408

> <EXACT_MASS>
296.065319146

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.927126597915844

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-dimethoxy-5'-(methylsulfanyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,4]thiazole]

> <ALOGPS_LOGP>
2.59

> <JCHEM_LOGP>
3.729777209

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.842429655753076

> <JCHEM_PKA_STRONGEST_BASIC>
3.4702485483377306

> <JCHEM_POLAR_SURFACE_AREA>
34.06

> <JCHEM_REFRACTIVITY>
90.0195

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.77e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dimethoxy-5'-(methylsulfanyl)-2H,3'H-spiro[indole-3,2'-[1,4]thiazole]

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041059
     RDKit          3D
N-Methoxyspirobrassinol methyl ether
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.5440   -2.9794    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.1776    0.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -0.8213    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -0.1124   -0.5632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.5236   -1.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.0269   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    1.1412   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411    2.2877   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    3.4070   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    3.3498   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    2.2268   -0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    1.0852   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -0.2258    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.1044   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -0.9936    0.0805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -0.5373    1.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -0.2936    2.0638 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261   -0.8191    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -0.1227    1.9272 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -2.7264    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557   -4.0267    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.9312    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -0.6346    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8332   -0.8458   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9169    0.6568    0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.5882   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    2.3345   -1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    4.3115   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    4.2157   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795    2.1541    0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401   -0.9383   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -2.1601   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398   -1.7472    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141   -0.9929    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0177    0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 13  3  1  0
 12  7  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.908   9.535   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.431   9.210   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.885   3.576   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.415   3.363   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.361   4.579   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.890   3.574   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.781   6.005   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.811   3.986   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.310   5.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.256   6.217   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.912   7.064   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.532   4.833   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.862   5.525   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.332   3.558   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.392   7.491   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       0.697   8.009   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       3.916   8.940   0.000  0.00  0.00           O+0
HETATM   18  S   UNK     0      -2.071   4.883   0.000  0.00  0.00           S+0
HETATM   19  S   UNK     0       0.414   6.048   0.000  0.00  0.00           S+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8   13   14                                                       
CONECT    9    6   10   13                                                  
CONECT   10    7    9   15                                                  
CONECT   11   13   15   16                                                  
CONECT   12   14   18   19                                                  
CONECT   13    8    9   11   19                                             
CONECT   14    8   12                                                       
CONECT   15   10   11   17                                                  
CONECT   16    1   11                                                       
CONECT   17    2   15                                                       
CONECT   18    3   12                                                       
CONECT   19   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0041059
HETATM    1  C1  UNL     1      -1.544  -2.979   1.222  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.072  -2.178   0.188  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.161  -0.821   0.485  1.00  0.00           C  
HETATM    4  N1  UNL     1      -1.914  -0.112  -0.563  1.00  0.00           N  
HETATM    5  O2  UNL     1      -3.025  -0.524  -1.216  1.00  0.00           O  
HETATM    6  C3  UNL     1      -4.184  -0.027  -0.591  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.267   1.141  -0.804  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.741   2.288  -1.453  1.00  0.00           C  
HETATM    9  C6  UNL     1      -0.947   3.407  -1.579  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.321   3.350  -1.043  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.797   2.227  -0.402  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.003   1.085  -0.270  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.190  -0.226   0.329  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.161  -1.104  -0.402  1.00  0.00           C  
HETATM   15  N2  UNL     1       2.448  -0.994   0.081  1.00  0.00           N  
HETATM   16  C12 UNL     1       2.686  -0.537   1.215  1.00  0.00           C  
HETATM   17  S1  UNL     1       4.249  -0.294   2.064  1.00  0.00           S  
HETATM   18  C13 UNL     1       5.626  -0.819   1.051  1.00  0.00           C  
HETATM   19  S2  UNL     1       1.090  -0.123   1.927  1.00  0.00           S  
HETATM   20  H1  UNL     1      -2.606  -2.726   1.402  1.00  0.00           H  
HETATM   21  H2  UNL     1      -1.556  -4.027   0.814  1.00  0.00           H  
HETATM   22  H3  UNL     1      -0.912  -2.931   2.113  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.584  -0.635   1.474  1.00  0.00           H  
HETATM   24  H5  UNL     1      -4.833  -0.846  -0.219  1.00  0.00           H  
HETATM   25  H6  UNL     1      -3.917   0.657   0.257  1.00  0.00           H  
HETATM   26  H7  UNL     1      -4.792   0.588  -1.287  1.00  0.00           H  
HETATM   27  H8  UNL     1      -2.736   2.334  -1.875  1.00  0.00           H  
HETATM   28  H9  UNL     1      -1.282   4.311  -2.075  1.00  0.00           H  
HETATM   29  H10 UNL     1       0.950   4.216  -1.134  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.779   2.154   0.025  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.040  -0.938  -1.494  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.810  -2.160  -0.215  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.440  -1.747   0.486  1.00  0.00           H  
HETATM   34  H15 UNL     1       6.514  -0.993   1.717  1.00  0.00           H  
HETATM   35  H16 UNL     1       5.974  -0.018   0.337  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4   13   23
CONECT    4    5    7
CONECT    5    6
CONECT    6   24   25   26
CONECT    7    8    8   12
CONECT    8    9   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   12   30
CONECT   12   13
CONECT   13   14   19
CONECT   14   15   31   32
CONECT   15   16   16
CONECT   16   17   19
CONECT   17   18
CONECT   18   33   34   35
END

HMDB0041059
     RDKit          3D
N-Methoxyspirobrassinol methyl ether
 35 37  0  0  0  0  0  0  0  0999 V2000
   -1.5440   -2.9794    1.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0722   -2.1776    0.1876 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1613   -0.8213    0.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9143   -0.1124   -0.5632 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0247   -0.5236   -1.2162 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1838   -0.0269   -0.5905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2673    1.1412   -0.8042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7411    2.2877   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9471    3.4070   -1.5788 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3214    3.3498   -1.0427 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7966    2.2268   -0.4022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0028    1.0852   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -0.2258    0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1614   -1.1044   -0.4018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4477   -0.9936    0.0805 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6863   -0.5373    1.2151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2487   -0.2936    2.0638 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6261   -0.8191    1.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -0.1227    1.9272 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6060   -2.7264    1.4020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5557   -4.0267    0.8138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9115   -2.9312    2.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842   -0.6346    1.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8332   -0.8458   -0.2186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9169    0.6568    0.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7920    0.5882   -1.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7358    2.3345   -1.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816    4.3115   -2.0752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    4.2157   -1.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795    2.1541    0.0246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401   -0.9383   -1.4940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8099   -2.1601   -0.2152 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4398   -1.7472    0.4857 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5141   -0.9929    1.7167 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9737   -0.0177    0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  4  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 16 19  1  0
 13  3  1  0
 12  7  1  0
 19 13  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  6 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-1-Methoxyspirobrassinol methyl ether	HMDB
1-Methoxyspirobrassinol methyl ether	HMDB
1,2-Dimethoxy-5'-(methylsulphanyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,4]thiazole]	Generator

Chemical Formula

C₁₃H₁₆N₂O₂S₂

Average Molecular Weight

296.408

Monoisotopic Molecular Weight

296.065319146

IUPAC Name

1,2-dimethoxy-5'-(methylsulfanyl)-1,2-dihydro-3'H-spiro[indole-3,2'-[1,4]thiazole]

Traditional Name

1,2-dimethoxy-5'-(methylsulfanyl)-2H,3'H-spiro[indole-3,2'-[1,4]thiazole]

CAS Registry Number

113866-41-4

SMILES

COC1N(OC)C2=CC=CC=C2C11CN=C(SC)S1

InChI Identifier

InChI=1S/C13H16N2O2S2/c1-16-11-13(8-14-12(18-3)19-13)9-6-4-5-7-10(9)15(11)17-2/h4-7,11H,8H2,1-3H3

InChI Key

KJSKSCBVIGFOKZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Not Available

Direct Parent

Indoles and derivatives

Alternative Parents

Substituents

Indole or derivatives
1-hydroxylamino, 4-unsubstituted benzenoid
1-hydroxylamino, 2-unsubstituted benzenoid
Benzenoid
Meta-thiazoline
Sulfenyl compound
Azacycle
N-organohydroxylamine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041059)
Cell membrane (HMDB: HMDB0041059)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041059)

Source

Exogenous

Exogenous (HMDB: HMDB0041059)

Food

Food (HMDB: HMDB0041059)

Vegetable

Root vegetable

Radish (FooDB: FOOD00153)

Brassica

Brassicas (FooDB: FOOD00857)

Endogenous

Plant

Plant (HMDB: HMDB0041059)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041059)

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	0.18 g/L	ALOGPS
logP	2.59	ALOGPS
logP	3.73	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	3.47	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	90.02 m³·mol⁻¹	ChemAxon
Polarizability	30.93 Å³	ChemAxon
Number of Rings	3	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]+	166.29	31661259
DarkChem	[M-H]-	163.521	31661259
DeepCCS	[M-2H]-	188.078	30932474
DeepCCS	[M+Na]+	163.623	30932474
AllCCS	[M+H]+	163.7	32859911
AllCCS	[M+H-H2O]+	160.4	32859911
AllCCS	[M+NH4]+	166.9	32859911
AllCCS	[M+Na]+	167.8	32859911
AllCCS	[M-H]-	167.5	32859911
AllCCS	[M+Na-2H]-	167.2	32859911
AllCCS	[M+HCOO]-	167.0	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.	4.2 minutes	32390414
Predicted by Siyang on May 30, 2022	16.0221 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2410.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	445.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	166.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	249.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	139.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	591.6 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	783.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	138.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1301.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	500.3 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	1710.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	372.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	469.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.3 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	44.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methoxyspirobrassinol methyl ether	COC1N(OC)C2=CC=CC=C2C11CN=C(SC)S1	3366.0	Standard polar	33892256
N-Methoxyspirobrassinol methyl ether	COC1N(OC)C2=CC=CC=C2C11CN=C(SC)S1	2194.3	Standard non polar	33892256
N-Methoxyspirobrassinol methyl ether	COC1N(OC)C2=CC=CC=C2C11CN=C(SC)S1	2258.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methoxyspirobrassinol methyl ether GC-MS (Non-derivatized) - 70eV, Positive	splash10-00vj-1890000000-9b71204d6749f0933790	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methoxyspirobrassinol methyl ether 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 - N-Methoxyspirobrassinol methyl ether 10V, Positive-QTOF	splash10-0002-8090000000-dc49c7682df5f3294cc4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 20V, Positive-QTOF	splash10-00kb-0090000000-00e7061687fb28f55422	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 40V, Positive-QTOF	splash10-00xv-3910000000-5f1b864ee1bf8d13dada	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 10V, Negative-QTOF	splash10-0a4i-0190000000-bcd8c4e6a3f0f7736df4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 20V, Negative-QTOF	splash10-0avi-7390000000-07122aedaebec1949ffa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 40V, Negative-QTOF	splash10-0a4i-9000000000-19b7045927cdb8197a76	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 10V, Positive-QTOF	splash10-0002-0090000000-850d3b0635973127eeee	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 20V, Positive-QTOF	splash10-0f6t-0090000000-e8d9178ce3e5f7b1686a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 40V, Positive-QTOF	splash10-0uk9-1690000000-3cc55b51fb82b01b5fe3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 10V, Negative-QTOF	splash10-0002-0090000000-c08eb31a9e56ce75929d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 20V, Negative-QTOF	splash10-0002-0090000000-ed7144e10e27fcb174a8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methoxyspirobrassinol methyl ether 40V, Negative-QTOF	splash10-0a4j-9550000000-dee2134f5dc244fefecf	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB020933

KNApSAcK ID

C00036441

Chemspider ID

8215801

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10040237

PDB ID

Not Available

ChEBI ID

169036

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 N-Methoxyspirobrassinol methyl ether (HMDB0041059)

MOL for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

3D MOL for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

3D SDF for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

3D-SDF for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

PDB for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

3D PDB for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

SMILES for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

INCHI for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

Structure for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

3D Structure for HMDB0041059 (N-Methoxyspirobrassinol methyl ether)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra