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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:52 UTC

Update Date

2022-03-07 02:52:02 UTC

HMDB ID

HMDB0015592

Secondary Accession Numbers

HMDB15592

Metabolite Identification

Common Name

Tetrabenazine

Description

Tetrabenazine, also known as nitoman or xenazine, belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. Tetrabenazine is a very strong basic compound (based on its pKa). A benzoquinolizine that is 1,2,3,4,4a,9,10,10a-octahydrophenanthrene in which the carbon at position 10a is replaced by a nitrogen and which is substituted by an isobutyl group at position 2, an oxo group at position 3, and methoxy groups at positions 6 and 7.

Structure

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

HMDB0015592
     RDKit          3D
Tetrabenazine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -5.0501   -3.1611    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -2.1152    0.2488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.3054    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -1.5323    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653   -0.7472    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008    0.2794    0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    0.5119   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -0.2811   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5360   -0.0396   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.9975   -2.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.1526    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012    1.1921   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    1.8239   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    2.5699   -1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    1.5356    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9546    1.3702    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    0.3091   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -1.0933   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    0.5162   -2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    0.3837    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6133    0.8971    1.5963 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    0.2526    2.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -1.0040    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183   -3.9147    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9785   -3.7178    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513   -2.7310    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -2.3482    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    1.3138   -1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3925    0.9655   -2.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.9707   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.9239   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    2.2030    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    1.7655   -1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    0.1621   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    2.4159    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3420    2.3487   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    1.2429    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5513    0.3497   -0.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.2378    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.4480   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -1.8204   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7535   -0.1799   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468    1.5235   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    0.1946   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    0.1128    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6438   -0.4747    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    0.0243    3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    0.9716    3.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.8691    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -1.2593    3.4287 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
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 21 11  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END


  Mrv0541 02231217572D          

 23 25  0  0  1  0            999 V2000
    5.2863    2.3071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499    0.2076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6499   -1.4822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2764   -0.2249    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619    0.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0337    1.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0271    0.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5487    1.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2764   -1.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2895    1.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7497    1.4622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -1.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8476   -1.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4625    1.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101    0.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1101   -1.4908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4593    0.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1785    1.4568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627   -1.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531    1.0325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6531   -2.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 11  2  0  0  0  0
  2 20  1  0  0  0  0
  2 22  1  0  0  0  0
  3 21  1  0  0  0  0
  3 23  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4  9  1  0  0  0  0
  5  8  1  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  6 12  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 10 16  2  0  0  0  0
 12 15  1  0  0  0  0
 13 14  1  0  0  0  0
 14 17  2  0  0  0  0
 15 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 17 21  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015592

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3

> <INCHI_KEY>
MKJIEFSOBYUXJB-UHFFFAOYSA-N

> <FORMULA>
C19H27NO3

> <MOLECULAR_WEIGHT>
317.4226

> <EXACT_MASS>
317.199093735

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.59489986304789

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

> <ALOGPS_LOGP>
3.23

> <JCHEM_LOGP>
3.4010616590000007

> <ALOGPS_LOGS>
-2.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.239992915266466

> <JCHEM_PKA_STRONGEST_BASIC>
7.411186284127676

> <JCHEM_POLAR_SURFACE_AREA>
38.77

> <JCHEM_REFRACTIVITY>
91.3074

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tetrabenazine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0015592
     RDKit          3D
Tetrabenazine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -5.0501   -3.1611    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -2.1152    0.2488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.3054    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -1.5323    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653   -0.7472    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008    0.2794    0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    0.5119   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -0.2811   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5360   -0.0396   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.9975   -2.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.1526    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012    1.1921   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    1.8239   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    2.5699   -1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    1.5356    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9546    1.3702    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    0.3091   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -1.0933   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    0.5162   -2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    0.3837    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6133    0.8971    1.5963 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    0.2526    2.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -1.0040    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183   -3.9147    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9785   -3.7178    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513   -2.7310    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -2.3482    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    1.3138   -1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3925    0.9655   -2.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.9707   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.9239   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    2.2030    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    1.7655   -1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    0.1621   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    2.4159    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3420    2.3487   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    1.2429    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5513    0.3497   -0.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.2378    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.4480   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -1.8204   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7535   -0.1799   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468    1.5235   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    0.1946   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    0.1128    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6438   -0.4747    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    0.0243    3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    0.9716    3.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.8691    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -1.2593    3.4287 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
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 21 11  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       9.868   4.307   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080   0.387   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.080  -2.767   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       9.849  -0.420   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       8.516   0.350   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.263   1.965   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.251   0.361   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.491   1.954   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.849  -1.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.182  -0.420   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.874   2.767   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      12.599   2.729   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.516  -2.730   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.182  -1.960   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.930   1.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.806   0.404   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.806  -2.783   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.924   0.415   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.267   2.719   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.410  -0.388   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.410  -1.992   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.086   1.927   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.086  -4.307   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   20   22                                                       
CONECT    3   21   23                                                       
CONECT    4    5    7    9                                                  
CONECT    5    4    8   10                                                  
CONECT    6    7   11   12                                                  
CONECT    7    4    6                                                       
CONECT    8    5   11                                                       
CONECT    9    4   13                                                       
CONECT   10    5   14   16                                                  
CONECT   11    1    6    8                                                  
CONECT   12    6   15                                                       
CONECT   13    9   14                                                       
CONECT   14   10   13   17                                                  
CONECT   15   12   18   19                                                  
CONECT   16   10   20                                                       
CONECT   17   14   21                                                       
CONECT   18   15                                                            
CONECT   19   15                                                            
CONECT   20    2   16   21                                                  
CONECT   21    3   17   20                                                  
CONECT   22    2                                                            
CONECT   23    3                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0015592
HETATM    1  C1  UNL     1      -5.050  -3.161   1.161  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.879  -2.115   0.249  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.735  -1.305   0.345  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.789  -1.532   1.324  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.665  -0.747   1.428  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.501   0.279   0.528  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.452   0.512  -0.461  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.584  -0.281  -0.563  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.536  -0.040  -1.562  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.394   0.998  -2.490  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.330   1.153   0.580  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.301   1.192  -0.817  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.645   1.824  -0.767  1.00  0.00           C  
HETATM   14  O3  UNL     1       1.998   2.570  -1.654  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.525   1.536   0.356  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.955   1.370   0.090  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.417   0.309  -0.820  1.00  0.00           C  
HETATM   18  C15 UNL     1       4.068  -1.093  -0.421  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.064   0.516  -2.278  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.894   0.384   1.149  1.00  0.00           C  
HETATM   21  N1  UNL     1       0.613   0.897   1.596  1.00  0.00           N  
HETATM   22  C18 UNL     1       0.126   0.253   2.773  1.00  0.00           C  
HETATM   23  C19 UNL     1      -0.660  -1.004   2.491  1.00  0.00           C  
HETATM   24  H1  UNL     1      -4.218  -3.915   1.084  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.978  -3.718   0.937  1.00  0.00           H  
HETATM   26  H3  UNL     1      -5.051  -2.731   2.194  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.919  -2.348   2.040  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.363   1.314  -1.193  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.393   0.965  -2.970  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.472   1.971  -1.971  1.00  0.00           H  
HETATM   31  H8  UNL     1      -5.208   0.924  -3.230  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.719   2.203   0.736  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.408   1.766  -1.449  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.334   0.162  -1.252  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.431   2.416   1.064  1.00  0.00           H  
HETATM   36  H13 UNL     1       4.342   2.349  -0.304  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.483   1.243   1.064  1.00  0.00           H  
HETATM   38  H15 UNL     1       5.551   0.350  -0.799  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.907  -1.238   0.652  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.205  -1.448  -1.055  1.00  0.00           H  
HETATM   41  H18 UNL     1       4.892  -1.820  -0.691  1.00  0.00           H  
HETATM   42  H19 UNL     1       4.753  -0.180  -2.846  1.00  0.00           H  
HETATM   43  H20 UNL     1       4.347   1.523  -2.617  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.054   0.195  -2.538  1.00  0.00           H  
HETATM   45  H22 UNL     1       2.479   0.113   2.027  1.00  0.00           H  
HETATM   46  H23 UNL     1       1.644  -0.475   0.478  1.00  0.00           H  
HETATM   47  H24 UNL     1       0.993   0.024   3.427  1.00  0.00           H  
HETATM   48  H25 UNL     1      -0.511   0.972   3.328  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.005  -1.869   2.259  1.00  0.00           H  
HETATM   50  H27 UNL     1      -1.200  -1.259   3.429  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   27
CONECT    5    6    6   23
CONECT    6    7   11
CONECT    7    8    8   28
CONECT    8    9
CONECT    9   10
CONECT   10   29   30   31
CONECT   11   12   21   32
CONECT   12   13   33   34
CONECT   13   14   14   15
CONECT   15   16   20   35
CONECT   16   17   36   37
CONECT   17   18   19   38
CONECT   18   39   40   41
CONECT   19   42   43   44
CONECT   20   21   45   46
CONECT   21   22
CONECT   22   23   47   48
CONECT   23   49   50
END

HMDB0015592
     RDKit          3D
Tetrabenazine
 50 52  0  0  0  0  0  0  0  0999 V2000
   -5.0501   -3.1611    1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8793   -2.1152    0.2488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7348   -1.3054    0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7889   -1.5323    1.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6653   -0.7472    1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5008    0.2794    0.5278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4520    0.5119   -0.4608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5835   -0.2811   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5360   -0.0396   -1.5620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3938    0.9975   -2.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3299    1.1526    0.5799 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3012    1.1921   -0.8171 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6449    1.8239   -0.7669 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9977    2.5699   -1.6539 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    1.5356    0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9546    1.3702    0.0899 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4172    0.3091   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0680   -1.0933   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0639    0.5162   -2.2778 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943    0.3837    1.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6133    0.8971    1.5963 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1263    0.2526    2.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6597   -1.0040    2.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2183   -3.9147    1.0837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9785   -3.7178    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0513   -2.7310    2.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9189   -2.3482    2.0396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3634    1.3138   -1.1931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3925    0.9655   -2.9703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4724    1.9707   -1.9706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2083    0.9239   -3.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7193    2.2030    0.7360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    1.7655   -1.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    0.1621   -1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4308    2.4159    1.0641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3420    2.3487   -0.3040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4826    1.2429    1.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5513    0.3497   -0.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9067   -1.2378    0.6523 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2046   -1.4480   -1.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8924   -1.8204   -0.6907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7535   -0.1799   -2.8455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3468    1.5235   -2.6170 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    0.1946   -2.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4794    0.1128    2.0268 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6438   -0.4747    0.4780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9928    0.0243    3.4270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5111    0.9716    3.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0051   -1.8691    2.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -1.2593    3.4287 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
  6 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  8  3  1  0
 21 11  1  0
 23  5  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 18 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,4,6,7,11b-Hexahydro-3-isobutyl-9,10-dimethoxy-2H-benzo[a]quinolizin-2-one	ChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11BH-benzo[a]quinolizine	ChEBI
2-oxo-3-Isobutyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizine	ChEBI
Nitoman	Kegg
Xenazine	Kegg
Ro 1-9569	HMDB
TBZ	HMDB
Tetra benazin	HMDB
Tetrabenzaine	HMDB
Tetrabenzine	HMDB
Tetrabenazine orphan brand	HMDB
Cambridge laboratories brand OF tetrabenazine	HMDB
Orphan brand OF tetrabenazine	HMDB
Roche brand OF tetrabenazine	HMDB
Shire brand OF tetrabenazine	HMDB
Tetrabenazine	MeSH

Chemical Formula

C₁₉H₂₇NO₃

Average Molecular Weight

317.4226

Monoisotopic Molecular Weight

317.199093735

IUPAC Name

9,10-dimethoxy-3-(2-methylpropyl)-1H,2H,3H,4H,6H,7H,11bH-pyrido[2,1-a]isoquinolin-2-one

Traditional Name

tetrabenazine

CAS Registry Number

58-46-8

SMILES

COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1

InChI Identifier

InChI=1S/C19H27NO3/c1-12(2)7-14-11-20-6-5-13-8-18(22-3)19(23-4)9-15(13)16(20)10-17(14)21/h8-9,12,14,16H,5-7,10-11H2,1-4H3

InChI Key

MKJIEFSOBYUXJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
Piperidinone
Aralkylamine
Piperidine
Benzenoid
Ketone
Tertiary amine
Tertiary aliphatic amine
Cyclic ketone
Ether
Azacycle
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:64028 )
tertiary amino compound (CHEBI:64028 )
benzoquinolizine (CHEBI:64028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0015592)
Membrane (HMDB: HMDB0015592)

Source

Exogenous

Exogenous (HMDB: HMDB0015592)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	128 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.36 g/L	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	182.6	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.36 g/L	ALOGPS
logP	3.23	ALOGPS
logP	3.4	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	18.24	ChemAxon
pKa (Strongest Basic)	7.41	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	38.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	91.31 m³·mol⁻¹	ChemAxon
Polarizability	36.59 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	176.403	31661259
DarkChem	[M-H]-	172.027	31661259
DeepCCS	[M+H]+	178.157	30932474
DeepCCS	[M-H]-	175.799	30932474
DeepCCS	[M-2H]-	208.745	30932474
DeepCCS	[M+Na]+	184.251	30932474
AllCCS	[M+H]+	178.2	32859911
AllCCS	[M+H-H2O]+	175.0	32859911
AllCCS	[M+NH4]+	181.1	32859911
AllCCS	[M+Na]+	182.0	32859911
AllCCS	[M-H]-	185.3	32859911
AllCCS	[M+Na-2H]-	185.7	32859911
AllCCS	[M+HCOO]-	186.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.83 minutes	32390414
Predicted by Siyang on May 30, 2022	10.4673 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.28 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	30.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1571.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	181.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	170.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	156.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	89.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	442.4 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	422.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	296.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	830.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	362.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1190.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	229.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	306.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	282.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	334.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tetrabenazine	COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1	3509.6	Standard polar	33892256
Tetrabenazine	COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1	2473.3	Standard non polar	33892256
Tetrabenazine	COC1=C(OC)C=C2C3CC(=O)C(CC(C)C)CN3CCC2=C1	2589.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tetrabenazine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C)=C(CC(C)C)CN1CC2	2573.9	Semi standard non polar	33892256
Tetrabenazine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C)=C(CC(C)C)CN1CC2	2581.9	Standard non polar	33892256
Tetrabenazine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C)=C(CC(C)C)CN1CC2	3308.2	Standard polar	33892256
Tetrabenazine,1TMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C)C(CC(C)C)CN1CC2	2534.1	Semi standard non polar	33892256
Tetrabenazine,1TMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C)C(CC(C)C)CN1CC2	2559.1	Standard non polar	33892256
Tetrabenazine,1TMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C)C(CC(C)C)CN1CC2	3347.3	Standard polar	33892256
Tetrabenazine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C(C)(C)C)=C(CC(C)C)CN1CC2	2826.9	Semi standard non polar	33892256
Tetrabenazine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C(C)(C)C)=C(CC(C)C)CN1CC2	2804.8	Standard non polar	33892256
Tetrabenazine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C1CC(O[Si](C)(C)C(C)(C)C)=C(CC(C)C)CN1CC2	3412.4	Standard polar	33892256
Tetrabenazine,1TBDMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C(C)(C)C)C(CC(C)C)CN1CC2	2793.9	Semi standard non polar	33892256
Tetrabenazine,1TBDMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C(C)(C)C)C(CC(C)C)CN1CC2	2754.9	Standard non polar	33892256
Tetrabenazine,1TBDMS,isomer #2	COC1=CC2=C(C=C1OC)C1C=C(O[Si](C)(C)C(C)(C)C)C(CC(C)C)CN1CC2	3449.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrabenazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6x-4292000000-399e16e38421335dc45d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrabenazine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tetrabenazine 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 - Tetrabenazine 10V, Positive-QTOF	splash10-014i-0019000000-02d6ea72dcc42a44288e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 20V, Positive-QTOF	splash10-014i-5269000000-f1240b2a09dcced1c899	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 40V, Positive-QTOF	splash10-0a4i-9430000000-cd11325cad96834bf22b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 10V, Negative-QTOF	splash10-014i-0009000000-484fd7bae49c0273c317	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 20V, Negative-QTOF	splash10-014j-7059000000-cbb7a83dafd4d674e753	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 40V, Negative-QTOF	splash10-0uec-9270000000-5581f9758fcb31092e0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 10V, Positive-QTOF	splash10-014i-0009000000-0041714e9cb69e8982f2	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 20V, Positive-QTOF	splash10-014i-0039000000-7d6e398b5d4a2227026e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 40V, Positive-QTOF	splash10-052f-9281000000-0c9b09c6cde8e368ca06	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 10V, Negative-QTOF	splash10-014i-0009000000-f61e4684d2f91b1d10d6	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 20V, Negative-QTOF	splash10-014i-0029000000-f7a121501bdf247273bc	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tetrabenazine 40V, Negative-QTOF	splash10-03di-1297000000-9bf4c9dd8adc56e35bd7	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04844	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB04844	21059682	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB04844

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

5796

KEGG Compound ID

C11168

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Tetrabenazine

METLIN ID

Not Available

PubChem Compound

6018

PDB ID

Not Available

ChEBI ID

64028

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

Jankovic J, Beach J: Long-term effects of tetrabenazine in hyperkinetic movement disorders. Neurology. 1997 Feb;48(2):358-62. [PubMed:9040721 ]
Guay DR: Tetrabenazine, a monoamine-depleting drug used in the treatment of hyperkinetic movement disorders. Am J Geriatr Pharmacother. 2010 Aug;8(4):331-73. doi: 10.1016/j.amjopharm.2010.08.006. [PubMed:20869622 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Poon LH, Kang GA, Lee AJ: Role of tetrabenazine for Huntington's disease-associated chorea. Ann Pharmacother. 2010 Jun;44(6):1080-9. doi: 10.1345/aph.1M582. Epub 2010 May 4. [PubMed:20442355 ]

Enzyme Details

2. Synaptic vesicular amine transporter

General function:: Involved in transmembrane transport
Specific function:: Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles. Requisite for vesicular amine storage prior to secretion via exocytosis
Gene Name:: SLC18A2
Uniprot ID:: Q05940
Molecular weight:: 55712.1

References

Zheng G, Dwoskin LP, Crooks PA: Vesicular monoamine transporter 2: role as a novel target for drug development. AAPS J. 2006 Nov 10;8(4):E682-92. [PubMed:17233532 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kim YS, Shin JH, Hall FS, Linden DJ: Dopamine signaling is required for depolarization-induced slow current in cerebellar Purkinje cells. J Neurosci. 2009 Jul 1;29(26):8530-8. doi: 10.1523/JNEUROSCI.0468-09.2009. [PubMed:19571144 ]
Goland R, Freeby M, Parsey R, Saisho Y, Kumar D, Simpson N, Hirsch J, Prince M, Maffei A, Mann JJ, Butler PC, Van Heertum R, Leibel RL, Ichise M, Harris PE: 11C-dihydrotetrabenazine PET of the pancreas in subjects with long-standing type 1 diabetes and in healthy controls. J Nucl Med. 2009 Mar;50(3):382-9. doi: 10.2967/jnumed.108.054866. Epub 2009 Feb 17. [PubMed:19223416 ]
Gros Y, Schuldiner S: Directed evolution reveals hidden properties of VMAT, a neurotransmitter transporter. J Biol Chem. 2010 Feb 12;285(7):5076-84. doi: 10.1074/jbc.M109.081216. Epub 2009 Dec 10. [PubMed:20007701 ]
Wimalasena K: Vesicular monoamine transporters: structure-function, pharmacology, and medicinal chemistry. Med Res Rev. 2011 Jul;31(4):483-519. doi: 10.1002/med.20187. Epub 2010 Feb 4. [PubMed:20135628 ]

Showing metabocard for Tetrabenazine (HMDB0015592)

MOL for HMDB0015592 (Tetrabenazine)

3D MOL for HMDB0015592 (Tetrabenazine)

3D SDF for HMDB0015592 (Tetrabenazine)

3D-SDF for HMDB0015592 (Tetrabenazine)

PDB for HMDB0015592 (Tetrabenazine)

3D PDB for HMDB0015592 (Tetrabenazine)

SMILES for HMDB0015592 (Tetrabenazine)

INCHI for HMDB0015592 (Tetrabenazine)

Structure for HMDB0015592 (Tetrabenazine)

3D Structure for HMDB0015592 (Tetrabenazine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References