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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:32:57 UTC

Update Date

2023-02-21 17:19:18 UTC

HMDB ID

HMDB0029835

Secondary Accession Numbers

HMDB29835

Metabolite Identification

Common Name

Tetrahydroharmol

Description

Tetrahydroharmol is found in fruits. Tetrahydroharmol is an alkaloid from Elaeagnus angustifolia (Russian olive) Harmaline is a reversible inhibitor of MAO-A (RIMA). Harmine is a reversible inhibitor of MAO-A (RIMA). It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors. Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine which was once known as Telepathine and Banisterine is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi, but not P. harmala. Dr. Alexander Shulgin has suggesed that harmaline may be a breakdown product of harmine. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine. The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3%, though tests have documented anywhere from 2-7%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline and 0.05-2.94% for tetrahydroharmine. Other psychoactive plants are often added to Ayahuasca to achieve visionary states of consciousness; for example leaves from Psychotria viridis, which is a source of dimethyltryptamine (DMT). The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are not especially psychoactive on their own, even at high dosages, when vomiting and diarrhea become the main effect

Structure

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

HMDB0029835
     RDKit          3D
Tetrahydroharmol
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.8106   -1.7519    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -1.0513   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700    0.0118   -0.5968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    1.1755   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995    0.8644   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422    0.2799   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.7036    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1835   -1.0828    1.0328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.3889    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671   -0.3884    1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    0.4631    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    0.4513    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.3297   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1488    1.3180   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    0.4771   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280   -1.1358    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2230   -2.7470    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -1.9488    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037   -1.8118   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    0.1680   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.6192   -1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    1.9568   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    0.1450   -2.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    1.7829   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.8155    1.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -1.0485    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5798   -0.1338    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.9847   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595    1.9806   -1.4446 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
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
M  END


  Mrv0541 02241216122D          

 15 17  0  0  0  0            999 V2000
    2.4305    0.2214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1761    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3689    1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8162    0.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0090    0.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5603    1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3690    1.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6219    0.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0705   -0.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647   -0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4036   -0.7053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718   -0.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8790   -0.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1320   -1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4305    0.0495    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  5 10  2  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029835

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1NCCC2=C1NC1=C2C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6-7,13-15H,4-5H2,1H3

> <INCHI_KEY>
AZTMWIPCEFFOJD-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O

> <MOLECULAR_WEIGHT>
202.2524

> <EXACT_MASS>
202.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
22.705260705409152

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <ALOGPS_LOGP>
1.58

> <JCHEM_LOGP>
1.2431738262445688

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.309750677533494

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.666803226402175

> <JCHEM_PKA_STRONGEST_BASIC>
8.96167395799267

> <JCHEM_POLAR_SURFACE_AREA>
48.05

> <JCHEM_REFRACTIVITY>
59.97929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.03e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029835
     RDKit          3D
Tetrahydroharmol
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.8106   -1.7519    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -1.0513   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700    0.0118   -0.5968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    1.1755   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995    0.8644   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422    0.2799   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.7036    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1835   -1.0828    1.0328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.3889    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671   -0.3884    1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    0.4631    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    0.4513    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.3297   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1488    1.3180   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    0.4771   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280   -1.1358    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2230   -2.7470    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -1.9488    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037   -1.8118   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    0.1680   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.6192   -1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    1.9568   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    0.1450   -2.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    1.7829   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.8155    1.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -1.0485    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5798   -0.1338    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.9847   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595    1.9806   -1.4446 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
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  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  N   UNK     0       4.537   0.413   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.062   1.879   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.555   2.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.524   1.055   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.017   1.055   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.046   2.197   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.555   1.879   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.028   0.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.998  -0.732   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.494  -0.411   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       0.753  -1.317   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.001  -0.411   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.507  -0.732   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.980  -2.197   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.537   0.092   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    4   11   13                                                  
CONECT   13    1   12   14                                                  
CONECT   14   13                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0029835
HETATM    1  C1  UNL     1      -2.811  -1.752   0.998  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.145  -1.051  -0.172  1.00  0.00           C  
HETATM    3  N1  UNL     1      -2.970   0.012  -0.597  1.00  0.00           N  
HETATM    4  C3  UNL     1      -2.324   1.176  -1.094  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.999   0.864  -1.703  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.142   0.280  -0.630  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.755  -0.704   0.144  1.00  0.00           C  
HETATM    8  N2  UNL     1       0.183  -1.083   1.033  1.00  0.00           N  
HETATM    9  C7  UNL     1       1.329  -0.389   0.845  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.567  -0.388   1.467  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.587   0.463   1.042  1.00  0.00           C  
HETATM   12  O1  UNL     1       4.823   0.451   1.676  1.00  0.00           O  
HETATM   13  C10 UNL     1       3.399   1.330  -0.005  1.00  0.00           C  
HETATM   14  C11 UNL     1       2.149   1.318  -0.621  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.144   0.477  -0.200  1.00  0.00           C  
HETATM   16  H1  UNL     1      -3.628  -1.136   1.431  1.00  0.00           H  
HETATM   17  H2  UNL     1      -3.223  -2.747   0.713  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.021  -1.949   1.769  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.104  -1.812  -1.006  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.829   0.168  -0.069  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.975   1.619  -1.901  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.151   1.957  -0.306  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.108   0.145  -2.539  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.520   1.783  -2.063  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.034  -1.816   1.764  1.00  0.00           H  
HETATM   26  H11 UNL     1       2.754  -1.048   2.287  1.00  0.00           H  
HETATM   27  H12 UNL     1       5.580  -0.134   1.401  1.00  0.00           H  
HETATM   28  H13 UNL     1       4.198   1.985  -0.325  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.960   1.981  -1.445  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    7   19
CONECT    3    4   20
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7    7   15
CONECT    7    8
CONECT    8    9   25
CONECT    9   10   10   15
CONECT   10   11   26
CONECT   11   12   13   13
CONECT   12   27
CONECT   13   14   28
CONECT   14   15   15   29
END

HMDB0029835
     RDKit          3D
Tetrahydroharmol
 29 31  0  0  0  0  0  0  0  0999 V2000
   -2.8106   -1.7519    0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1453   -1.0513   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9700    0.0118   -0.5968 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3243    1.1755   -1.0936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995    0.8644   -1.7032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422    0.2799   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7551   -0.7036    0.1441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1835   -1.0828    1.0328 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3292   -0.3889    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5671   -0.3884    1.4666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5866    0.4631    1.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    0.4513    1.6764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989    1.3297   -0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1488    1.3180   -0.6207 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1442    0.4771   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6280   -1.1358    1.4315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2230   -2.7470    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0214   -1.9488    1.7690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1037   -1.8118   -1.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8291    0.1680   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.6192   -1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1513    1.9568   -0.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1075    0.1450   -2.5392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5202    1.7829   -2.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0337   -1.8155    1.7636 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7541   -1.0485    2.2866 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5798   -0.1338    1.4009 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1978    1.9847   -0.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9595    1.9806   -1.4446 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
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
  7  2  1  0
 15  9  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  8 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-7-hydroxy-1-methyl-b-carboline	HMDB
2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indol-7-ol, 8ci	HMDB
Tetrahydroharmalol hydrochloride	HMDB
Tetrahydroharmol hydrochloride	HMDB

Chemical Formula

C₁₂H₁₄N₂O

Average Molecular Weight

202.2524

Monoisotopic Molecular Weight

202.11061308

IUPAC Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

Traditional Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

CAS Registry Number

17952-75-9

SMILES

CC1NCCC2=C1NC1=C2C=CC(O)=C1

InChI Identifier

InChI=1S/C12H14N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6-7,13-15H,4-5H2,1H3

InChI Key

AZTMWIPCEFFOJD-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harmaline
Harmalol
Harman
Beta-carboline
Pyridoindole
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Organoheterocyclic compound
Azacycle
Secondary aliphatic amine
Secondary amine
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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: HMDB0029835)
Cytoplasm (HMDB: HMDB0029835)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029835)

Source

Endogenous

Endogenous (HMDB: HMDB0029835)

Plant

Plant (HMDB: HMDB0029835)

Exogenous

Food

Food (HMDB: HMDB0029835)

Fruit

Fruits (FooDB: FOOD00871)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	254 - 255 °C	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	0.5 g/L	ALOGPS
logP	1.58	ALOGPS
logP	1.24	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	48.05 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	59.98 m³·mol⁻¹	ChemAxon
Polarizability	22.71 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	144.995	31661259
DarkChem	[M-H]-	144.56	31661259
DeepCCS	[M+H]+	142.742	30932474
DeepCCS	[M-H]-	140.211	30932474
DeepCCS	[M-2H]-	175.735	30932474
DeepCCS	[M+Na]+	151.258	30932474
AllCCS	[M+H]+	145.7	32859911
AllCCS	[M+H-H2O]+	141.4	32859911
AllCCS	[M+NH4]+	149.7	32859911
AllCCS	[M+Na]+	150.8	32859911
AllCCS	[M-H]-	149.9	32859911
AllCCS	[M+Na-2H]-	149.8	32859911
AllCCS	[M+HCOO]-	149.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydroharmol	CC1NCCC2=C1NC1=C2C=CC(O)=C1	3315.1	Standard polar	33892256
Tetrahydroharmol	CC1NCCC2=C1NC1=C2C=CC(O)=C1	2116.1	Standard non polar	33892256
Tetrahydroharmol	CC1NCCC2=C1NC1=C2C=CC(O)=C1	2333.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydroharmol,1TMS,isomer #1	CC1NCCC2=C1[NH]C1=CC(O[Si](C)(C)C)=CC=C21	2259.3	Semi standard non polar	33892256
Tetrahydroharmol,1TMS,isomer #2	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O)C=C1[NH]2	2385.2	Semi standard non polar	33892256
Tetrahydroharmol,1TMS,isomer #3	CC1NCCC2=C1N([Si](C)(C)C)C1=CC(O)=CC=C21	2300.6	Semi standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1[NH]2	2347.8	Semi standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1[NH]2	2299.4	Standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C)C1=CC(O[Si](C)(C)C)=CC=C21	2264.2	Semi standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C)C1=CC(O[Si](C)(C)C)=CC=C21	2086.5	Standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O)C=C1N2[Si](C)(C)C	2339.9	Semi standard non polar	33892256
Tetrahydroharmol,2TMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O)C=C1N2[Si](C)(C)C	2357.6	Standard non polar	33892256
Tetrahydroharmol,3TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1N2[Si](C)(C)C	2306.1	Semi standard non polar	33892256
Tetrahydroharmol,3TMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C=C1N2[Si](C)(C)C	2308.3	Standard non polar	33892256
Tetrahydroharmol,1TBDMS,isomer #1	CC1NCCC2=C1[NH]C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2509.0	Semi standard non polar	33892256
Tetrahydroharmol,1TBDMS,isomer #2	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1[NH]2	2607.7	Semi standard non polar	33892256
Tetrahydroharmol,1TBDMS,isomer #3	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC(O)=CC=C21	2516.4	Semi standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1[NH]2	2810.1	Semi standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1[NH]2	2778.7	Standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2683.3	Semi standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #2	CC1NCCC2=C1N([Si](C)(C)C(C)(C)C)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	2557.1	Standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1N2[Si](C)(C)C(C)(C)C	2723.0	Semi standard non polar	33892256
Tetrahydroharmol,2TBDMS,isomer #3	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O)C=C1N2[Si](C)(C)C(C)(C)C	2824.9	Standard non polar	33892256
Tetrahydroharmol,3TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1N2[Si](C)(C)C(C)(C)C	2905.4	Semi standard non polar	33892256
Tetrahydroharmol,3TBDMS,isomer #1	CC1C2=C(CCN1[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1N2[Si](C)(C)C(C)(C)C	2967.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-0910000000-70bfd23f847e808c0f3e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmol GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-3690000000-b50240f2dfd89efd370a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmol 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 - Tetrahydroharmol 10V, Positive-QTOF	splash10-0udi-0190000000-dbf0ba828934a3d16b85	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 20V, Positive-QTOF	splash10-0w29-1950000000-cd07495fb3fab4274fb4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 40V, Positive-QTOF	splash10-052f-0900000000-a9ba3cd5545cb553e8b7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 10V, Negative-QTOF	splash10-0udi-0090000000-54e3ee3f4a7697515db6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 20V, Negative-QTOF	splash10-0udi-0190000000-ffda0c873192bf93a9c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 40V, Negative-QTOF	splash10-0ac9-2900000000-8947f0a5c18fbf6a5813	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 10V, Negative-QTOF	splash10-0udi-0090000000-53c3fa4c5460be246d0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 20V, Negative-QTOF	splash10-0udi-0090000000-53c3fa4c5460be246d0c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 40V, Negative-QTOF	splash10-053s-0900000000-a644d6e5d295344f8a9f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 10V, Positive-QTOF	splash10-0udi-0090000000-ee2fb06e46c3edc2e07a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 20V, Positive-QTOF	splash10-0udi-0190000000-85a10545fbc1fd164f55	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmol 40V, Positive-QTOF	splash10-08g0-2900000000-4bc929863d4e520a914d	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX 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

FDB001050

KNApSAcK ID

C00057972

Chemspider ID

327573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrahydroharmol

METLIN ID

Not Available

PubChem Compound

368982

PDB ID

Not Available

ChEBI ID

114202

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 Tetrahydroharmol (HMDB0029835)

MOL for HMDB0029835 (Tetrahydroharmol)

3D MOL for HMDB0029835 (Tetrahydroharmol)

3D SDF for HMDB0029835 (Tetrahydroharmol)

3D-SDF for HMDB0029835 (Tetrahydroharmol)

PDB for HMDB0029835 (Tetrahydroharmol)

3D PDB for HMDB0029835 (Tetrahydroharmol)

SMILES for HMDB0029835 (Tetrahydroharmol)

INCHI for HMDB0029835 (Tetrahydroharmol)

Structure for HMDB0029835 (Tetrahydroharmol)

3D Structure for HMDB0029835 (Tetrahydroharmol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra