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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 13:01:45 UTC

Update Date

2021-09-26 23:07:42 UTC

HMDB ID

HMDB0254015

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Tetrahydroharmine

Description

Leptaflorine, also known as tetrahydroharmine, 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. Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015). Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi. A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. Leptaflorine is a very strong basic compound (based on its pKa). THH weakly inhibits serotonin reuptake. THH does not inhibit monoamine oxidase B, however two other harmala alkaloids in B. caapi, harmaline and harmine, are reversible inhibitors of monoamine oxidase A. While THH may not play a significant role in the inhibition of MAO it may contribute psychoactivity indirectly by inhibiting the uptake of Serotonin in platelets and presynaptic neurons . This compound has been identified in human blood as reported by (PMID: 31557052 ). Tetrahydroharmine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Tetrahydroharmine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0254015
     RDKit          3D
Tetrahydroharmine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.0307    1.3170    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.0133    0.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -0.2830    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.6070   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -1.8832   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -0.8966   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -0.8585   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.4343   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    1.1862    0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    0.4164   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432    0.7085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.6902   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899    1.9795    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -0.3811    0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575   -1.5975    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -1.9191   -0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5007    2.0107   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.5997    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222    1.3795    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -2.3683   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -2.8872   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    2.2329    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    1.7343    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    0.9052   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.7699    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    2.5302    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.6500   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1377    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.5800    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049   -2.4019    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.7991   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -2.9309   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  3  1  0
 10  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

  Mrv1533004241519492D          

 16 18  0  0  0  0            999 V2000
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544   -0.7152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0254015

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3

> <INCHI_KEY>
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.284

> <EXACT_MASS>
216.126263143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.930443888684195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.8491500276666664

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.304032245419247

> <JCHEM_PKA_STRONGEST_BASIC>
8.815955364534469

> <JCHEM_POLAR_SURFACE_AREA>
37.05

> <JCHEM_REFRACTIVITY>
64.4616

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0254015
     RDKit          3D
Tetrahydroharmine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.0307    1.3170    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.0133    0.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -0.2830    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.6070   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -1.8832   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -0.8966   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -0.8585   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.4343   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    1.1862    0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    0.4164   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432    0.7085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.6902   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899    1.9795    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -0.3811    0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575   -1.5975    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -1.9191   -0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5007    2.0107   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.5997    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222    1.3795    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -2.3683   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -2.8872   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    2.2329    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    1.7343    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    0.9052   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.7699    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    2.5302    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.6500   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1377    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.5800    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049   -2.4019    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.7991   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -2.9309   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  3  1  0
 10  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.155  -1.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
CONECT   15   12   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0254015
HETATM    1  C1  UNL     1       5.031   1.317   0.383  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.569  -0.013   0.203  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.217  -0.283   0.080  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.831  -1.607  -0.095  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.495  -1.883  -0.218  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.524  -0.897  -0.174  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.842  -0.858  -0.264  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.297   0.434  -0.152  1.00  0.00           C  
HETATM    9  N1  UNL     1      -0.190   1.186   0.008  1.00  0.00           N  
HETATM   10  C8  UNL     1       0.915   0.416  -0.001  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.243   0.709   0.123  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.747   0.690  -0.224  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.090   1.979   0.510  1.00  0.00           C  
HETATM   14  N2  UNL     1      -3.578  -0.381   0.193  1.00  0.00           N  
HETATM   15  C12 UNL     1      -2.957  -1.598   0.570  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.858  -1.919  -0.451  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.501   2.011  -0.299  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.868   1.600   1.441  1.00  0.00           H  
HETATM   19  H3  UNL     1       6.122   1.379   0.144  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.590  -2.368  -0.127  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.164  -2.887  -0.352  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.216   2.233   0.123  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.558   1.734   0.259  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.975   0.905  -1.308  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.625   1.770   1.464  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.170   2.530   0.783  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.725   2.650  -0.087  1.00  0.00           H  
HETATM   28  H12 UNL     1      -4.444  -0.138   0.676  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.453  -1.580   1.553  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.705  -2.402   0.584  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.313  -1.799  -1.441  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.443  -2.931  -0.286  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   10
CONECT    7    8    8   16
CONECT    8    9   12
CONECT    9   10   22
CONECT   10   11   11
CONECT   11   23
CONECT   12   13   14   24
CONECT   13   25   26   27
CONECT   14   15   28
CONECT   15   16   29   30
CONECT   16   31   32
END

HMDB0254015
     RDKit          3D
Tetrahydroharmine
 32 34  0  0  0  0  0  0  0  0999 V2000
    5.0307    1.3170    0.3829 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5693   -0.0133    0.2029 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -0.2830    0.0795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8310   -1.6070   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4954   -1.8832   -0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5241   -0.8966   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8424   -0.8585   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2966    0.4343   -0.1517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1896    1.1862    0.0085 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9154    0.4164   -0.0011 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2432    0.7085    0.1230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7475    0.6902   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0899    1.9795    0.5102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5783   -0.3811    0.1928 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9575   -1.5975    0.5701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8581   -1.9191   -0.4510 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5007    2.0107   -0.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    1.5997    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1222    1.3795    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5898   -2.3683   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1641   -2.8872   -0.3523 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2162    2.2329    0.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5584    1.7343    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9748    0.9052   -1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6250    1.7699    1.4640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1701    2.5302    0.7826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7252    2.6500   -0.0866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4441   -0.1377    0.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4530   -1.5800    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049   -2.4019    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3127   -1.7991   -1.4411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4433   -2.9309   -0.2855 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 11  3  1  0
 10  6  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  9 22  1  0
 11 23  1  0
 12 24  1  0
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Tetrahydroharmine	MeSH
1,2,3,4-Tetrahydroharmine	MeSH

Chemical Formula

C₁₃H₁₆N₂O

Average Molecular Weight

216.284

Monoisotopic Molecular Weight

216.126263143

IUPAC Name

7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

Traditional Name

7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1

InChI Identifier

InChI=1S/C13H16N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-4,7-8,14-15H,5-6H2,1-2H3

InChI Key

ZXLDQJLIBNPEFJ-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
Harman
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary amine
Azacycle
Ether
Secondary aliphatic amine
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	2.09	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	16.3	ChemAxon
pKa (Strongest Basic)	8.82	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.05 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.46 m³·mol⁻¹	ChemAxon
Polarizability	24.93 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
DeepCCS	[M+H]+	157.786	30932474
DeepCCS	[M-H]-	155.391	30932474
DeepCCS	[M-2H]-	188.298	30932474
DeepCCS	[M+Na]+	163.814	30932474
AllCCS	[M+H]+	151.9	32859911
AllCCS	[M+H-H2O]+	148.0	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.5	32859911
AllCCS	[M-H]-	153.3	32859911
AllCCS	[M+Na-2H]-	153.3	32859911
AllCCS	[M+HCOO]-	153.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydroharmine	COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1	3225.3	Standard polar	33892256
Tetrahydroharmine	COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1	2059.5	Standard non polar	33892256
Tetrahydroharmine	COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1	2261.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrahydroharmine,1TMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C)C2=C1	2256.7	Semi standard non polar	33892256
Tetrahydroharmine,1TMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C)C2=C1	2048.6	Standard non polar	33892256
Tetrahydroharmine,1TMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C)C2=C1	2591.4	Standard polar	33892256
Tetrahydroharmine,1TMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C)CC3	2315.6	Semi standard non polar	33892256
Tetrahydroharmine,1TMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C)CC3	2245.2	Standard non polar	33892256
Tetrahydroharmine,1TMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C)CC3	2721.6	Standard polar	33892256
Tetrahydroharmine,2TMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C)CC3)N([Si](C)(C)C)C2=C1	2264.3	Semi standard non polar	33892256
Tetrahydroharmine,2TMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C)CC3)N([Si](C)(C)C)C2=C1	2286.6	Standard non polar	33892256
Tetrahydroharmine,2TMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C)CC3)N([Si](C)(C)C)C2=C1	2488.0	Standard polar	33892256
Tetrahydroharmine,1TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C(C)(C)C)C2=C1	2440.3	Semi standard non polar	33892256
Tetrahydroharmine,1TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C(C)(C)C)C2=C1	2289.1	Standard non polar	33892256
Tetrahydroharmine,1TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)NCC3)N([Si](C)(C)C(C)(C)C)C2=C1	2696.3	Standard polar	33892256
Tetrahydroharmine,1TBDMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C(C)(C)C)CC3	2552.4	Semi standard non polar	33892256
Tetrahydroharmine,1TBDMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C(C)(C)C)CC3	2474.5	Standard non polar	33892256
Tetrahydroharmine,1TBDMS,isomer #2	COC1=CC=C2C3=C([NH]C2=C1)C(C)N([Si](C)(C)C(C)(C)C)CC3	2914.3	Standard polar	33892256
Tetrahydroharmine,2TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C(C)(C)C)CC3)N([Si](C)(C)C(C)(C)C)C2=C1	2652.5	Semi standard non polar	33892256
Tetrahydroharmine,2TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C(C)(C)C)CC3)N([Si](C)(C)C(C)(C)C)C2=C1	2720.2	Standard non polar	33892256
Tetrahydroharmine,2TBDMS,isomer #1	COC1=CC=C2C3=C(C(C)N([Si](C)(C)C(C)(C)C)CC3)N([Si](C)(C)C(C)(C)C)C2=C1	2739.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uk9-0930000000-4c184374a876545d7f01	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrahydroharmine 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 - Tetrahydroharmine 10V, Positive-QTOF	splash10-014i-0090000000-b3b3217a7e594f652193	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmine 20V, Positive-QTOF	splash10-01b9-0690000000-6304e017d872a91b0939	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmine 40V, Positive-QTOF	splash10-00xr-1930000000-0d84c739ef6e6210bc14	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmine 10V, Negative-QTOF	splash10-014i-0090000000-810ec31dac75bb9d724b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmine 20V, Negative-QTOF	splash10-014i-0490000000-ea487dba85e0bf97d8a5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrahydroharmine 40V, Negative-QTOF	splash10-00ea-0900000000-0f960b93d64d645936a2	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrahydroharmine

METLIN ID

Not Available

PubChem Compound

159809

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Tetrahydroharmine (HMDB0254015)

MOL for HMDB0254015 (Tetrahydroharmine)

3D MOL for HMDB0254015 (Tetrahydroharmine)

3D SDF for HMDB0254015 (Tetrahydroharmine)

3D-SDF for HMDB0254015 (Tetrahydroharmine)

PDB for HMDB0254015 (Tetrahydroharmine)

3D PDB for HMDB0254015 (Tetrahydroharmine)

SMILES for HMDB0254015 (Tetrahydroharmine)

INCHI for HMDB0254015 (Tetrahydroharmine)

Structure for HMDB0254015 (Tetrahydroharmine)

3D Structure for HMDB0254015 (Tetrahydroharmine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra