MiMeDB: Showing metabocard for N-Demethylsambutoxin (MMDBc0003270)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:23:06 UTC

Update Date

2025-10-07 16:04:42 UTC

Metabolite ID

MMDBc0003270

Metabolite Identification

Common Name

N-Demethylsambutoxin

Description

N-Demethylsambutoxin is a secondary metabolite belonging to the class of alkaloids. It has been identified as a product of fungal metabolism, specifically isolated from cultures of Fusarium species, indicating its potential ecological role and biological activity. In a study, N-Demethylsambutoxin was found alongside other compounds such as sambutoxin and fusaramin, highlighting its presence in complex natural mixtures (PMID:31204387 ). Additionally, it was isolated during bioassay-guided fractionation from Fusarium oxysporum, where it was categorized with several other known and novel compounds, suggesting its relevance in the context of fungal secondary metabolite research (PMID:16562855 ). The structural characteristics and biological implications of N-Demethylsambutoxin warrant further investigation, particularly regarding its potential pharmacological effects and mechanisms of action, given the increasing interest in fungal metabolites for therapeutic applications.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305142123232D          

 38 40  0  0  1  0            999 V2000
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 16  2  1  1  0  0  0
 16  6  1  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  6  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  1  0  0  0
 18  7  1  0  0  0  0
 19  5  1  0  0  0  0
 19 14  2  0  0  0  0
 20  8  2  0  0  0  0
 20  9  1  0  0  0  0
 21 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 15  2  0  0  0  0
 22 20  1  0  0  0  0
 23 12  1  0  0  0  0
 23 24  1  6  0  0  0
 25 22  1  0  0  0  0
 25 24  2  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  6  0  0  0
 27 24  1  0  0  0  0
 28 15  1  0  0  0  0
 28 27  2  0  0  0  0
 29 21  1  0  0  0  0
 30 25  1  0  0  0  0
 31 27  1  0  0  0  0
 32 23  1  0  0  0  0
 32 26  1  0  0  0  0
 33 14  1  0  0  0  0
 16 34  1  6  0  0  0
 17 35  1  1  0  0  0
 18 36  1  6  0  0  0
 23 37  1  1  0  0  0
 26 38  1  1  0  0  0
M  END


  Mrv1652305142123232D          

 38 40  0  0  1  0            999 V2000
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.1447   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.0026    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  1  0  0  0  0
 16  2  1  1  0  0  0
 16  6  1  0  0  0  0
 16 13  1  0  0  0  0
 17  3  1  6  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
 18  4  1  1  0  0  0
 18  7  1  0  0  0  0
 19  5  1  0  0  0  0
 19 14  2  0  0  0  0
 20  8  2  0  0  0  0
 20  9  1  0  0  0  0
 21 10  2  0  0  0  0
 21 11  1  0  0  0  0
 22 15  2  0  0  0  0
 22 20  1  0  0  0  0
 23 12  1  0  0  0  0
 23 24  1  6  0  0  0
 25 22  1  0  0  0  0
 25 24  2  0  0  0  0
 26 18  1  0  0  0  0
 26 19  1  6  0  0  0
 27 24  1  0  0  0  0
 28 15  1  0  0  0  0
 28 27  2  0  0  0  0
 29 21  1  0  0  0  0
 30 25  1  0  0  0  0
 31 27  1  0  0  0  0
 32 23  1  0  0  0  0
 32 26  1  0  0  0  0
 33 14  1  0  0  0  0
 16 34  1  6  0  0  0
 17 35  1  1  0  0  0
 18 36  1  6  0  0  0
 23 37  1  1  0  0  0
 26 38  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0003270

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\C)[C@]1([H])O[C@@]([H])(CC[C@@]1([H])C)C1=C(O)C(=CN=C1O)C1=CC=C(O)C=C1)[C@]([H])(C)C[C@@]([H])(C)CC

> <INCHI_IDENTIFIER>
InChI=1S/C27H37NO4/c1-6-16(2)13-17(3)14-19(5)26-18(4)7-12-23(32-26)24-25(30)22(15-28-27(24)31)20-8-10-21(29)11-9-20/h8-11,14-18,23,26,29H,6-7,12-13H2,1-5H3,(H2,28,30,31)/b19-14+/t16-,17+,18+,23-,26+/m0/s1

> <INCHI_KEY>
YDGOHTBOOYAVOP-JYCRKZTRSA-N

> <FORMULA>
C27H37NO4

> <MOLECULAR_WEIGHT>
439.596

> <EXACT_MASS>
439.272258675

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.748064517917584

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2S,5R,6R)-6-[(2E,4R,6S)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

> <ALOGPS_LOGP>
6.23

> <JCHEM_LOGP>
7.010769092666666

> <ALOGPS_LOGS>
-4.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.849441111610314

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.911982099154557

> <JCHEM_PKA_STRONGEST_BASIC>
0.8250234555774977

> <JCHEM_POLAR_SURFACE_AREA>
82.81000000000002

> <JCHEM_REFRACTIVITY>
129.43399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.35e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2S,5R,6R)-6-[(2E,4R,6S)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 14-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-21         0                                  
HETATM    1  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      13.337  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.005  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.004   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      14.670   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.005  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.672   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.338   3.850   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.672   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.338  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      20.005   3.850   0.000  0.00  0.00           N+0
HETATM   29  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      16.004   1.540   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      21.339   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      17.338  -0.770   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0      14.670  -0.770   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0       9.336  -3.850   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      12.003  -3.850   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      17.338  -3.850   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      20.005   0.770   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      16.004  -1.540   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    1   16                                                       
CONECT    7   12   18                                                       
CONECT    8   10   20                                                       
CONECT    9   11   20                                                       
CONECT   10    8   21                                                       
CONECT   11    9   21                                                       
CONECT   12    7   23                                                       
CONECT   13   16   17                                                       
CONECT   14   17   19   33                                                  
CONECT   15   22   28                                                       
CONECT   16    2    6   13   34                                             
CONECT   17    3   13   14   35                                             
CONECT   18    4    7   26   36                                             
CONECT   19    5   14   26                                                  
CONECT   20    8    9   22                                                  
CONECT   21   10   11   29                                                  
CONECT   22   15   20   25                                                  
CONECT   23   12   24   32   37                                             
CONECT   24   23   25   27                                                  
CONECT   25   22   24   30                                                  
CONECT   26   18   19   32   38                                             
CONECT   27   24   28   31                                                  
CONECT   28   15   27                                                       
CONECT   29   21                                                            
CONECT   30   25                                                            
CONECT   31   27                                                            
CONECT   32   23   26                                                       
CONECT   33   14                                                            
CONECT   34   16                                                            
CONECT   35   17                                                            
CONECT   36   18                                                            
CONECT   37   23                                                            
CONECT   38   26                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

Synonyms

Not Available

Molecular Formula

C₂₇H₃₇NO₄

Average Mass

439.596

Monoisotopic Mass

439.272258675

IUPAC Name

3-[(2S,5R,6R)-6-[(2E,4R,6S)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

Traditional Name

3-[(2S,5R,6R)-6-[(2E,4R,6S)-4,6-dimethyloct-2-en-2-yl]-5-methyloxan-2-yl]-5-(4-hydroxyphenyl)pyridine-2,4-diol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\C)[C@]1([H])O[C@@]([H])(CC[C@@]1([H])C)C1=C(O)C(=CN=C1O)C1=CC=C(O)C=C1)[C@]([H])(C)C[C@@]([H])(C)CC

InChI Identifier

InChI=1S/C27H37NO4/c1-6-16(2)13-17(3)14-19(5)26-18(4)7-12-23(32-26)24-25(30)22(15-28-27(24)31)20-8-10-21(29)11-9-20/h8-11,14-18,23,26,29H,6-7,12-13H2,1-5H3,(H2,28,30,31)/b19-14+/t16-,17+,18+,23-,26+/m0/s1

InChI Key

YDGOHTBOOYAVOP-JYCRKZTRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
3-phenylpyridine
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
1-hydroxy-2-unsubstituted benzenoid
Dihydropyridine
Pyridinone
Hydroxypyridine
Phenol
Monocyclic benzene moiety
Pyridine
Oxane
Benzenoid
Hydropyridine
Vinylogous acid
Heteroaromatic compound
Lactam
Azacycle
Oxacycle
Ether
Dialkyl ether
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.0054 g/L	ALOGPS
logP	6.23	ALOGPS
logP	7.01	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	5.91	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	82.81 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	129.43 m³·mol⁻¹	ChemAxon
Polarizability	51.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-20	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	47.2
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	33.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	665.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	816.4
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1083.2
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	428.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2789.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	85.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	225.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	677.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	185.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	197.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	261.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	8.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	225.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	554.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	491.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1782.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1676.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	N-Demethylsambutoxin_TMS_1	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard non polar	2025-10-23	1734.46
Gas Chromatography	N-Demethylsambutoxin_TMS_2	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O)C=C3)=C2O)CC[C@H]1C	standard non polar	2025-10-23	1423.83
Gas Chromatography	N-Demethylsambutoxin_TMS_3	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O)CC[C@H]1C	standard non polar	2025-10-23	2116.13
Gas Chromatography	N-Demethylsambutoxin_TMS_4	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard non polar	2025-10-23	2365.45
Gas Chromatography	N-Demethylsambutoxin_TMS_5	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard non polar	2025-10-23	1617.66
Gas Chromatography	N-Demethylsambutoxin_TMS_6	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O)CC[C@H]1C	standard non polar	2025-10-23	2510.37
Gas Chromatography	N-Demethylsambutoxin_TMS_7	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard non polar	2025-10-23	1996.83
Gas Chromatography	N-Demethylsambutoxin_TMS_1	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard polar	2025-10-23	1569.46
Gas Chromatography	N-Demethylsambutoxin_TMS_2	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O)C=C3)=C2O)CC[C@H]1C	standard polar	2025-10-23	2559.88
Gas Chromatography	N-Demethylsambutoxin_TMS_3	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O)CC[C@H]1C	standard polar	2025-10-23	2528.85
Gas Chromatography	N-Demethylsambutoxin_TMS_4	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard polar	2025-10-23	1783.55
Gas Chromatography	N-Demethylsambutoxin_TMS_5	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard polar	2025-10-23	1825.86
Gas Chromatography	N-Demethylsambutoxin_TMS_6	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O)CC[C@H]1C	standard polar	2025-10-23	999.511
Gas Chromatography	N-Demethylsambutoxin_TMS_7	CC[C@H](C)C[C@@H](C)/C=C(\C)[C@@H]1O[C@H](C2=C(O[Si](C)(C)C)N=CC(C3=CC=C(O[Si](C)(C)C)C=C3)=C2O[Si](C)(C)C)CC[C@H]1C	standard polar	2025-10-23	2272.5

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78442489

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139583791

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for N-Demethylsambutoxin (MMDBc0003270)

MOL for #<Metabolite:0x00007f2df9634e98>

3D MOL for #<Metabolite:0x00007f2df9634e98>

3D SDF for #<Metabolite:0x00007f2df9634e98>

3D-SDF for #<Metabolite:0x00007f2df9634e98>

PDB for #<Metabolite:0x00007f2df9634e98>

3D PDB for #<Metabolite:0x00007f2df9634e98>

SMILES for #<Metabolite:0x00007f2df9634e98>

INCHI for #<Metabolite:0x00007f2df9634e98>

Structure for #<Metabolite:0x00007f2df9634e98>

3D Structure for #<Metabolite:0x00007f2df9634e98>