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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:18:07 UTC

Update Date

2021-09-14 15:48:24 UTC

HMDB ID

HMDB0061098

Secondary Accession Numbers

HMDB61098

Metabolite Identification

Common Name

alpha-dihydrotetrabenazine

Description

alpha-dihydrotetrabenazine is a metabolite of tetrabenazine. Tetrabenazine is a drug for the symptomatic treatment of hyperkinetic movement disorder and is marketed under the trade names Nitoman in Canada and Xenazine in New Zealand and some parts of Europe, and is also available in the USA as an orphan drug. On August 15, 2008 the U.S. Food and Drug Administration (FDA) approved the use of tetrabenazine to treat chorea associated with Huntington's disease (HD), the first in the US. The compound has been known since the 1950s. (Wikipedia)

Structure

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

HMDB0061098
     RDKit          3D
alpha-dihydrotetrabenazine
 52 54  0  0  0  0  0  0  0  0999 V2000
   -6.3486   -1.6290   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8301   -0.9526   -0.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4973   -0.5661   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774   -0.8439   -1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546   -0.4695   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    0.1842   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    0.4466    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374    0.0900    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8681    0.3668    1.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    1.0484    2.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    0.6285   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504    0.0565    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -0.0977    0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0386   -1.4384    0.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.8083   -0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7373    0.6244   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    0.8252    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.5852   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7059    0.0801    1.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5617    0.7844   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125    0.3789   -1.4422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773   -0.9117   -2.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.7937   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601   -2.6665   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1124   -1.0727   -2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4364   -1.6652   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -1.3729   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205    0.9728    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9883    1.1982    3.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8955    2.0300    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688    0.5143    3.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.7488   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.9572    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.6675    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848    0.0663    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509   -2.0348    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    1.8871    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.3995   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251    1.2923   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    1.9192    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9574    1.0076    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1508    1.1290   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859   -0.4880   -0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -0.9395    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.0015    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    0.6627    2.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    1.8014   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    0.1103   -2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444   -1.7214   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.2015   -2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122   -1.7457   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.0539   -3.3072 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  1  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
 13 35  1  1
 14 36  1  0
 15 37  1  1
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
M  END


  Mrv0541 07091309182D          

 23 25  0  0  0  0            999 V2000
   -2.1730    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9355    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3480    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3645    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0145   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  7  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  1  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 17 14  1  0  0  0  0
 18  8  1  0  0  0  0
 19  9  1  0  0  0  0
 19 18  2  0  0  0  0
 20  6  1  0  0  0  0
 20 11  1  0  0  0  0
 20 16  1  0  0  0  0
 17 21  1  1  0  0  0
 22  3  1  0  0  0  0
 22 18  1  0  0  0  0
 23  4  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061098

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H29NO3/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/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16?,17+/m0/s1

> <INCHI_KEY>
WEQLWGNDNRARGE-DRXWIORDSA-N

> <FORMULA>
C19H29NO3

> <MOLECULAR_WEIGHT>
319.4385

> <EXACT_MASS>
319.214743799

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
37.16776269872673

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.672495206333334

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.847956288719477

> <JCHEM_PKA_STRONGEST_BASIC>
8.265522325632105

> <JCHEM_POLAR_SURFACE_AREA>
41.93000000000001

> <JCHEM_REFRACTIVITY>
92.39819999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061098
     RDKit          3D
alpha-dihydrotetrabenazine
 52 54  0  0  0  0  0  0  0  0999 V2000
   -6.3486   -1.6290   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8301   -0.9526   -0.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4973   -0.5661   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774   -0.8439   -1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546   -0.4695   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    0.1842   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    0.4466    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374    0.0900    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8681    0.3668    1.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    1.0484    2.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    0.6285   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504    0.0565    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -0.0977    0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0386   -1.4384    0.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.8083   -0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7373    0.6244   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    0.8252    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.5852   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7059    0.0801    1.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5617    0.7844   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125    0.3789   -1.4422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773   -0.9117   -2.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.7937   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601   -2.6665   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1124   -1.0727   -2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4364   -1.6652   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -1.3729   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205    0.9728    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9883    1.1982    3.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8955    2.0300    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688    0.5143    3.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.7488   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.9572    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.6675    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848    0.0663    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509   -2.0348    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    1.8871    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.3995   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251    1.2923   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    1.9192    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9574    1.0076    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1508    1.1290   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859   -0.4880   -0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -0.9395    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.0015    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    0.6627    2.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    1.8014   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    0.1103   -2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444   -1.7214   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.2015   -2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122   -1.7457   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.0539   -3.3072 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  1  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
 13 35  1  1
 14 36  1  0
 15 37  1  1
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
M  END

HEADER    PROTEIN                                 09-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-JUL-13         0                                  
HETATM    1  C   UNK     0      -4.056   2.104   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.746   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.034  -1.897   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.746   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.516   2.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.104   2.104   0.000  0.00  0.00           N+0
HETATM   21  O   UNK     0      -0.206  -1.897   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.034   0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       7.494  -1.897   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   22                                                            
CONECT    4   23                                                            
CONECT    5    6   13                                                       
CONECT    6    5   20                                                       
CONECT    7   12   14                                                       
CONECT    8   13   18                                                       
CONECT    9   15   19                                                       
CONECT   10   16   17                                                       
CONECT   11   14   20                                                       
CONECT   12    1    2    7                                                  
CONECT   13    5    8   15                                                  
CONECT   14    7   11   17                                                  
CONECT   15    9   13   16                                                  
CONECT   16   10   15   20                                                  
CONECT   17   10   14   21                                                  
CONECT   18    8   19   22                                                  
CONECT   19    9   18   23                                                  
CONECT   20    6   11   16                                                  
CONECT   21   17                                                            
CONECT   22    3   18                                                       
CONECT   23    4   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0061098
HETATM    1  C1  UNL     1      -6.349  -1.629  -1.505  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.830  -0.953  -0.375  1.00  0.00           O  
HETATM    3  C2  UNL     1      -4.497  -0.566  -0.341  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.677  -0.844  -1.414  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.355  -0.470  -1.400  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.858   0.184  -0.305  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.700   0.447   0.749  1.00  0.00           C  
HETATM    8  C7  UNL     1      -4.037   0.090   0.781  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.868   0.367   1.859  1.00  0.00           O  
HETATM   10  C8  UNL     1      -4.288   1.048   2.963  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.432   0.629  -0.203  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.250   0.057   1.001  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.755  -0.098   0.798  1.00  0.00           C  
HETATM   14  O3  UNL     1       2.039  -1.438   0.445  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.302   0.808  -0.210  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.737   0.624  -0.526  1.00  0.00           C  
HETATM   17  C14 UNL     1       4.771   0.825   0.504  1.00  0.00           C  
HETATM   18  C15 UNL     1       6.161   0.585  -0.166  1.00  0.00           C  
HETATM   19  C16 UNL     1       4.706   0.080   1.775  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.562   0.784  -1.537  1.00  0.00           C  
HETATM   21  N1  UNL     1       0.212   0.379  -1.442  1.00  0.00           N  
HETATM   22  C18 UNL     1      -0.077  -0.912  -2.020  1.00  0.00           C  
HETATM   23  C19 UNL     1      -1.497  -0.794  -2.594  1.00  0.00           C  
HETATM   24  H1  UNL     1      -5.960  -2.667  -1.577  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.112  -1.073  -2.448  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.436  -1.665  -1.391  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.084  -1.373  -2.298  1.00  0.00           H  
HETATM   28  H5  UNL     1      -2.320   0.973   1.642  1.00  0.00           H  
HETATM   29  H6  UNL     1      -4.988   1.198   3.788  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.896   2.030   2.569  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.369   0.514   3.331  1.00  0.00           H  
HETATM   32  H9  UNL     1      -0.485   1.749  -0.067  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.152  -0.957   1.183  1.00  0.00           H  
HETATM   34  H11 UNL     1       0.020   0.668   1.893  1.00  0.00           H  
HETATM   35  H12 UNL     1       2.185   0.066   1.783  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.951  -2.035   1.222  1.00  0.00           H  
HETATM   37  H14 UNL     1       2.226   1.887   0.179  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.927  -0.399  -0.994  1.00  0.00           H  
HETATM   39  H16 UNL     1       4.025   1.292  -1.423  1.00  0.00           H  
HETATM   40  H17 UNL     1       4.806   1.919   0.760  1.00  0.00           H  
HETATM   41  H18 UNL     1       6.957   1.008   0.463  1.00  0.00           H  
HETATM   42  H19 UNL     1       6.151   1.129  -1.133  1.00  0.00           H  
HETATM   43  H20 UNL     1       6.286  -0.488  -0.306  1.00  0.00           H  
HETATM   44  H21 UNL     1       4.292  -0.939   1.749  1.00  0.00           H  
HETATM   45  H22 UNL     1       5.792  -0.002   2.168  1.00  0.00           H  
HETATM   46  H23 UNL     1       4.227   0.663   2.604  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.616   1.801  -1.975  1.00  0.00           H  
HETATM   48  H25 UNL     1       2.082   0.110  -2.268  1.00  0.00           H  
HETATM   49  H26 UNL     1      -0.144  -1.721  -1.263  1.00  0.00           H  
HETATM   50  H27 UNL     1       0.651  -1.201  -2.776  1.00  0.00           H  
HETATM   51  H28 UNL     1      -1.812  -1.746  -3.068  1.00  0.00           H  
HETATM   52  H29 UNL     1      -1.464   0.054  -3.307  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   15   35
CONECT   14   36
CONECT   15   16   20   37
CONECT   16   17   38   39
CONECT   17   18   19   40
CONECT   18   41   42   43
CONECT   19   44   45   46
CONECT   20   21   47   48
CONECT   21   22
CONECT   22   23   49   50
CONECT   23   51   52
END

HMDB0061098
     RDKit          3D
alpha-dihydrotetrabenazine
 52 54  0  0  0  0  0  0  0  0999 V2000
   -6.3486   -1.6290   -1.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8301   -0.9526   -0.3750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4973   -0.5661   -0.3408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6774   -0.8439   -1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3546   -0.4695   -1.4000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8577    0.1842   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7005    0.4466    0.7490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0374    0.0900    0.7808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8681    0.3668    1.8587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2877    1.0484    2.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4315    0.6285   -0.2035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2504    0.0565    1.0007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -0.0977    0.7978 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0386   -1.4384    0.4453 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3022    0.8083   -0.2097 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7373    0.6244   -0.5259 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7709    0.8252    0.5039 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1614    0.5852   -0.1658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7059    0.0801    1.7755 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5617    0.7844   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2125    0.3789   -1.4422 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0773   -0.9117   -2.0205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.7937   -2.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9601   -2.6665   -1.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1124   -1.0727   -2.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4364   -1.6652   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -1.3729   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205    0.9728    1.6419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9883    1.1982    3.7877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8955    2.0300    2.5690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3688    0.5143    3.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846    1.7488   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1517   -0.9572    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0204    0.6675    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1848    0.0663    1.7832 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509   -2.0348    1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2263    1.8871    0.1788 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9267   -0.3995   -0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0251    1.2923   -1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8055    1.9192    0.7597 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9574    1.0076    0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1508    1.1290   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2859   -0.4880   -0.3060 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2915   -0.9395    1.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7920   -0.0015    2.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2267    0.6627    2.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6155    1.8014   -1.9746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    0.1103   -2.2679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1444   -1.7214   -1.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6513   -1.2015   -2.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8122   -1.7457   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4641    0.0539   -3.3072 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  1  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
 13 35  1  1
 14 36  1  0
 15 37  1  1
 16 38  1  0
 16 39  1  0
 17 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 19 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  0
 22 50  1  0
 23 51  1  0
 23 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Dihydrotetrabenazine	Generator
Α-dihydrotetrabenazine	Generator

Chemical Formula

C₁₉H₂₉NO₃

Average Molecular Weight

319.4385

Monoisotopic Molecular Weight

319.214743799

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1

InChI Identifier

InChI=1S/C19H29NO3/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/h8-9,12,14,16-17,21H,5-7,10-11H2,1-4H3/t14-,16?,17+/m0/s1

InChI Key

WEQLWGNDNRARGE-DRXWIORDSA-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
Aralkylamine
Piperidine
Benzenoid
Secondary alcohol
Tertiary amine
Tertiary aliphatic amine
Ether
Azacycle
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Alcohol
Organic oxygen compound
Amine
Hydrocarbon derivative
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 (HMDB: HMDB0061098)

Organ

Kidney (HMDB: HMDB0061098)
Liver (HMDB: HMDB0061098)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061098)

Cellular substructure

Cytoplasm (HMDB: HMDB0061098)
Membrane (HMDB: HMDB0061098)

Source

Endogenous

Endogenous (HMDB: HMDB0061098)

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
Water Solubility	0.28 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.67	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	14.85	ChemAxon
pKa (Strongest Basic)	8.27	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	92.4 m³·mol⁻¹	ChemAxon
Polarizability	37.17 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]+	176.131	31661259
DarkChem	[M-H]-	176.046	31661259
DeepCCS	[M+H]+	182.825	30932474
DeepCCS	[M-H]-	180.467	30932474
DeepCCS	[M-2H]-	214.354	30932474
DeepCCS	[M+Na]+	189.582	30932474
AllCCS	[M+H]+	179.7	32859911
AllCCS	[M+H-H2O]+	176.6	32859911
AllCCS	[M+NH4]+	182.6	32859911
AllCCS	[M+Na]+	183.4	32859911
AllCCS	[M-H]-	185.5	32859911
AllCCS	[M+Na-2H]-	186.0	32859911
AllCCS	[M+HCOO]-	186.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-dihydrotetrabenazine	COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1	3479.2	Standard polar	33892256
alpha-dihydrotetrabenazine	COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1	2417.1	Standard non polar	33892256
alpha-dihydrotetrabenazine	COC1=C(OC)C=C2C3C[C@@H](O)[C@@H](CC(C)C)CN3CCC2=C1	2623.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-dihydrotetrabenazine,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C1C[C@@H](O[Si](C)(C)C)[C@@H](CC(C)C)CN1CC2	2540.0	Semi standard non polar	33892256
alpha-dihydrotetrabenazine,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C1C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](CC(C)C)CN1CC2	2788.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-dihydrotetrabenazine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ufu-3292000000-616bc16f49d880cae9ed	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-dihydrotetrabenazine GC-MS (1 TMS) - 70eV, Positive	splash10-004i-8249000000-d0bbf8d456350af0aeef	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-dihydrotetrabenazine 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 - alpha-dihydrotetrabenazine 10V, Positive-QTOF	splash10-0uk9-0009000000-9c277b99782b8216a454	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 20V, Positive-QTOF	splash10-0zmi-4059000000-c1e43ba5cc1445d72ed7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 40V, Positive-QTOF	splash10-0a4i-9160000000-55276a50fa5b351231c5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 10V, Negative-QTOF	splash10-014i-0009000000-09a82e4b00c48172cc45	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 20V, Negative-QTOF	splash10-0gb9-0039000000-8d2acd244003542952ff	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 40V, Negative-QTOF	splash10-001i-3940000000-60f86c3141ca9b72260f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 10V, Negative-QTOF	splash10-014i-0009000000-53a97113085b5fcc385f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 20V, Negative-QTOF	splash10-014i-0039000000-4cb6994d57e2ef4d7c73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 40V, Negative-QTOF	splash10-03di-0191000000-d7833e906f014ec43363	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 10V, Positive-QTOF	splash10-00di-0009000000-c7fe7dbeb850d8698185	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 20V, Positive-QTOF	splash10-00di-0029000000-bdc12adf769c55736cc1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-dihydrotetrabenazine 40V, Positive-QTOF	splash10-0kml-4191000000-8b66742b9f56ae2b0858	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

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	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	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

Not Available

METLIN ID

Not Available

PubChem Compound

57378128

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

Not Available

Showing metabocard for alpha-dihydrotetrabenazine (HMDB0061098)

MOL for HMDB0061098 (alpha-dihydrotetrabenazine)

3D MOL for HMDB0061098 (alpha-dihydrotetrabenazine)

3D SDF for HMDB0061098 (alpha-dihydrotetrabenazine)

3D-SDF for HMDB0061098 (alpha-dihydrotetrabenazine)

PDB for HMDB0061098 (alpha-dihydrotetrabenazine)

3D PDB for HMDB0061098 (alpha-dihydrotetrabenazine)

SMILES for HMDB0061098 (alpha-dihydrotetrabenazine)

INCHI for HMDB0061098 (alpha-dihydrotetrabenazine)

Structure for HMDB0061098 (alpha-dihydrotetrabenazine)

3D Structure for HMDB0061098 (alpha-dihydrotetrabenazine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra