MiMeDB: Showing metabocard for Bufotenin (MMDBc0000674)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:27 UTC

Update Date

2024-10-11 01:03:33 UTC

Metabolite ID

MMDBc0000674

Metabolite Identification

Common Name

Bufotenin

Description

A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic. Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America.

Structure

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

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

1445
  Mrv1652304062013062D          

 15 16  0  0  0  0            999 V2000
    2.0930   -0.1082    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3370    1.4693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -1.5972    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2734    0.5149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171   -0.2693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0807    0.6851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2365   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4986   -0.9332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -0.1082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5220   -1.7582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -0.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1443    1.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7860    2.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8075   -1.3457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2  7  1  0  0  0  0
  2 13  1  0  0  0  0
  2 14  1  0  0  0  0
  3  8  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6  8  2  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 10 12  2  0  0  0  0
 11 15  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000674

> <DATABASE_NAME>
MIME

> <SMILES>
CN(C)CCC1=CNC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

> <INCHI_KEY>
VTTONGPRPXSUTJ-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.2682

> <EXACT_MASS>
204.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.290220670308504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

> <ALOGPS_LOGP>
2.04

> <JCHEM_LOGP>
1.2922694904624674

> <ALOGPS_LOGS>
-1.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.218197203699578

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.232412171709068

> <JCHEM_PKA_STRONGEST_BASIC>
9.910793391467232

> <JCHEM_POLAR_SURFACE_AREA>
39.26

> <JCHEM_REFRACTIVITY>
62.423100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.20e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bufotenine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

HEADER    PROTEIN                                 06-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1445                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-APR-20         0                                  
HETATM    1  O   UNK     0       3.907  -0.202   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      11.829   2.743   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       9.365  -2.981   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.844   0.961   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.365  -0.503   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.908  -0.972   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.351   1.279   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.908  -2.512   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.264  -1.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -0.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.574  -3.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.241  -0.972   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.336   3.060   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.801   3.889   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.241  -2.512   0.000  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2    7   13   14                                                  
CONECT    3    8    9                                                       
CONECT    4    5    7                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    8   10                                                  
CONECT    7    2    4                                                       
CONECT    8    3    6   11                                                  
CONECT    9    3    5                                                       
CONECT   10    6   12                                                       
CONECT   11    8   15                                                       
CONECT   12    1   10   15                                                  
CONECT   13    2                                                            
CONECT   14    2                                                            
CONECT   15   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0041842
HETATM    1  C1  UNL     1      -3.637   0.359   0.891  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.777  -0.774   0.649  1.00  0.00           N  
HETATM    3  C2  UNL     1      -3.518  -1.840  -0.047  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.678  -0.318  -0.184  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.844   0.638   0.613  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.327   1.138  -0.138  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.492   2.307  -0.847  1.00  0.00           C  
HETATM    8  N2  UNL     1       1.723   2.310  -1.387  1.00  0.00           N  
HETATM    9  C7  UNL     1       2.394   1.178  -1.062  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.670   0.714  -1.355  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.125  -0.504  -0.879  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.260  -1.240  -0.098  1.00  0.00           C  
HETATM   13  O1  UNL     1       3.697  -2.464   0.394  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.990  -0.781   0.195  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.521   0.447  -0.282  1.00  0.00           C  
HETATM   16  H1  UNL     1      -4.658  -0.017   1.107  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.632   1.017   0.021  1.00  0.00           H  
HETATM   18  H3  UNL     1      -3.182   0.887   1.771  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.834  -2.388  -0.725  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.341  -1.343  -0.574  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.842  -2.545   0.739  1.00  0.00           H  
HETATM   22  H7  UNL     1      -1.097  -1.191  -0.540  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.044   0.210  -1.101  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.395   1.505   1.020  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.491   0.059   1.521  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.297   3.062  -0.916  1.00  0.00           H  
HETATM   27  H12 UNL     1       2.147   3.056  -1.980  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.314   1.303  -1.956  1.00  0.00           H  
HETATM   29  H14 UNL     1       5.130  -0.861  -1.108  1.00  0.00           H  
HETATM   30  H15 UNL     1       4.172  -2.578   1.282  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.303  -1.346   0.806  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    7   15
CONECT    7    8   26
CONECT    8    9   27
CONECT    9   10   10   15
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   14
CONECT   13   30
CONECT   14   15   15   31
END

HMDB0041842
     RDKit          3D
Bufotenin
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.6372    0.3594    0.8906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7772   -0.7742    0.6489 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5183   -1.8396   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6785   -0.3176   -0.1842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8439    0.6383    0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3273    1.1379   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4922    2.3067   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7230    2.3096   -1.3867 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3944    1.1775   -1.0618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6703    0.7136   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1251   -0.5037   -0.8787 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2604   -1.2403   -0.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6973   -2.4636    0.3943 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9899   -0.7808    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5210    0.4466   -0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6578   -0.0174    1.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6317    1.0172    0.0212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1825    0.8868    1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8336   -2.3883   -0.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3408   -1.3429   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -2.5453    0.7391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0969   -1.1906   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    0.2098   -1.1011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3947    1.5050    1.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4915    0.0587    1.5212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2972    3.0624   -0.9159 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1470    3.0562   -1.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3144    1.3027   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1296   -0.8606   -1.1085 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1719   -2.5779    1.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3033   -1.3456    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  6  1  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
M  END

Synonyms

Value	Source
3-[2-(Dimethylamino)ethyl]-5-indolol	ChEBI
3-[2-(Dimethylamino)ethyl]indol-5-ol	ChEBI
3-[beta-(Dimethylamino)ethyl]-5-hydroxyindole	ChEBI
5-Hydroxy-N,N-dimethyltryptamine	ChEBI
Bufotenine	ChEBI
DM5-HT	ChEBI
N,N-Dimethylserotonin	ChEBI
3-[b-(Dimethylamino)ethyl]-5-hydroxyindole	Generator
3-[Β-(dimethylamino)ethyl]-5-hydroxyindole	Generator
1H-indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)	HMDB
3-(2-Dimethylaminoethyl)-5-indolol	HMDB
3-(2-Dimethylaminoethyl)indol-5-ol	HMDB
3-(beta-Dimethylaminoethyl)-5-hydroxyindole	HMDB
3-[2-(Dimethylamino)ethyl]-1H-indol-5-ol	HMDB
3-[2-(Dimethylamino)ethyl]-indol-5-ol	HMDB
5-Hydroxy-N, N-dimethyltryptamine	HMDB
Cinobufotenine	HMDB
Cohoba	HMDB
Dimethylserotonin	HMDB
indol-5-Ol, {3-[2-(dimethylamino)ethyl]-}	HMDB
Mapine	HMDB
Mappin	HMDB
Mappine	HMDB
N, N-Dimethylserotonin	HMDB
N,N-Dimethyl-5-hydroxytryptamine	HMDB
{3-[(2-dimethylamino)ethyl]-5-indolol}	HMDB
{3-[(beta-dimethylamino)ethyl]-5-hydroxyindole}	HMDB
N,N Dimethyl 5 hydroxytryptamine	HMDB
5 Hydroxy N,N dimethyltryptamine	HMDB
Bufotenin	KEGG

Molecular Formula

C₁₂H₁₆N₂O

Average Mass

204.2682

Monoisotopic Mass

204.126263144

IUPAC Name

3-[2-(dimethylamino)ethyl]-1H-indol-5-ol

Traditional Name

bufotenine

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=CNC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C12H16N2O/c1-14(2)6-5-9-8-13-12-4-3-10(15)7-11(9)12/h3-4,7-8,13,15H,5-6H2,1-2H3

InChI Key

VTTONGPRPXSUTJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Hydroxyindole
3-alkylindole
Indole
Alkaloid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amine (CHEBI:3210 )
tryptamine alkaloid (CHEBI:3210 )
Indole alkaloids (C08299 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.2 g/L	ALOGPS
logP	2.04	ALOGPS
logP	1.29	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.23	ChemAxon
pKa (Strongest Basic)	9.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.42 m³·mol⁻¹	ChemAxon
Polarizability	23.29 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-0af816b35b1e16d258a1	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9130000000-7bbf336895ab1b156223	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-af3dd65f76ad8654b621	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-08fr-0940000000-8952400d2cb6d011de82	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01qa-1900000000-34b8e0879f296431d1e8	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-59bc27deb381d771d0ae	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1290000000-c4aa46abeccd608387a9	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0536-5900000000-1b322d788e0c55bfa242	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190000000-aa5796e407ec72620b1b	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-0970000000-fa89d4528ce714421e8a	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-001i-1900000000-df031839bb432c50ef0d	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0190000000-7230690add489b3c18b9	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0bt9-1950000000-42c05e07b418d453a0a8	2021-09-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8900000000-cd0c40dcec1955a75dcb	2021-09-22	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9100000000-3e8c21621c306ca36dec	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

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

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0010289	S-Adenosylmethionine	S-Adenosylhomocysteine	indolethylamine N-methyltransferase		VMH; KEGG	30371894

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
Bacteria	Firmicutes	1	Human stool; Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified				HMDB
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0041842

DrugBank ID

DB01445

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bufotenin

METLIN ID

Not Available

PubChem Compound

10257

PDB ID

Not Available

ChEBI ID

3210

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Carpenter WT Jr, Fink EB, Narasimhachari N, Himwich HE: A test of the transmethylation hypothesis in acute schizophrenic patients. Am J Psychiatry. 1975 Oct;132(10):1067-71. doi: 10.1176/ajp.132.10.1067. [PubMed:1058643 ]
Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. doi: 10.1097/00001756-199511270-00024. [PubMed:8747157 ]
Ciprian-Ollivier J, Cetkovich-Bakmas MG: Altered consciousness states and endogenous psychoses: a common molecular pathway? Schizophr Res. 1997 Dec 19;28(2-3):257-65. doi: 10.1016/s0920-9964(97)00116-3. [PubMed:9468359 ]
Pomilio AB, Vitale AA, Ciprian-Ollivier J, Cetkovich-Bakmas M, Gomez R, Vazquez G: Ayahoasca: an experimental psychosis that mirrors the transmethylation hypothesis of schizophrenia. J Ethnopharmacol. 1999 Apr;65(1):29-51. doi: 10.1016/s0378-8741(98)00163-9. [PubMed:10350367 ]
Sponheim E, Myhre AM, Reichelt KL, Aalen OO: [Urine peptide patterns in children with milder types of autism]. Tidsskr Nor Laegeforen. 2006 May 25;126(11):1475-7. [PubMed:16732341 ]

Showing metabocard for Bufotenin (MMDBc0000674)

MOL for #<Metabolite:0x00007fdb1bf84758>

3D MOL for #<Metabolite:0x00007fdb1bf84758>

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3D-SDF for #<Metabolite:0x00007fdb1bf84758>

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3D PDB for #<Metabolite:0x00007fdb1bf84758>

SMILES for #<Metabolite:0x00007fdb1bf84758>

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Structure for #<Metabolite:0x00007fdb1bf84758>

3D Structure for #<Metabolite:0x00007fdb1bf84758>