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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-09 16:15:58 UTC

Update Date

2019-07-23 07:15:41 UTC

HMDB ID

HMDB0061061

Secondary Accession Numbers

HMDB61061

Metabolite Identification

Common Name

9'-desmethylgranisetron

Description

9'-desmethylgranisetron is a metabolite of granisetron. Granisetron is a serotonin 5-HT3 receptor antagonist used as an antiemetic to treat nausea and vomiting following chemotherapy. Its main effect is to reduce the activity of the vagus nerve, which is a nerve that activates the vomiting center in the medulla oblongata. It does not have much effect on vomiting due to motion sickness. This drug does not have any effect on dopamine receptors or muscarinic receptors. (Wikipedia)

Structure

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

HMDB0061061
     RDKit          3D
9'-desmethylgranisetron
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1758   -2.1153    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -1.1872    0.2807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361   -0.7014   -1.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8121    0.4829   -1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892    1.5381   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0905    0.8718    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0090   -0.1727    1.2651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6391    0.4227    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -0.1803    0.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4613    0.4619   -0.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -0.1689    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.3678    0.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.5397   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    1.8397   -0.3899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315    2.1159   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    1.0311   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5225    0.8139   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9783   -0.4381    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0956   -1.4752    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.1949    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399    0.0409    0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.2385   -1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -2.5993    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433   -2.9279   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -1.6880    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -1.4996   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.9573   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432    0.2008   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8230    2.0402   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    2.2866   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0466    0.3235    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886    1.5754    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -0.6342    2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6549    1.5201    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    0.1271    2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -1.2490    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.4864   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8410    3.0561   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2602    1.5734   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319   -0.6848    0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4680   -2.4568    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -1.9666    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.0408   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6817   -1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
  7  2  1  0
 21 13  1  0
 22  3  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  1
 10 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 22 44  1  0
M  END


  Mrv0541 07091309152D          

 24 27  0  0  0  0            999 V2000
    2.1310    0.5900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1929   -1.4572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7062   -2.1031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1175   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2444   -0.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6220   -0.9357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3769   -1.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4035   -2.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2248   -1.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290   -1.9119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8127   -2.0914    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1634   -0.5574    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5820   -0.9250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0742   -2.3463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5875   -2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3013   -2.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6135   -2.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1249   -2.5470    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -3.6799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3369   -3.4591    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7132   -0.1214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6643   -1.3558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.2013    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1480   -0.3248    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  2  0  0  0  0
 15  8  2  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  1  0  0  0  0
 11 18  1  1  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20 16  2  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21 12  1  0  0  0  0
 21 13  1  0  0  0  0
 22 17  2  0  0  0  0
 12 23  1  6  0  0  0
 13 24  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0061061

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CCC[C@]([H])(C[C@@H](C1)NC(=O)C1=NNC3=CC=CC=C13)N2C

> <INCHI_IDENTIFIER>
InChI=1S/C17H22N4O/c1-21-12-5-4-6-13(21)10-11(9-12)18-17(22)16-14-7-2-3-8-15(14)19-20-16/h2-3,7-8,11-13H,4-6,9-10H2,1H3,(H,18,22)(H,19,20)/t11-,12+,13-

> <INCHI_KEY>
GHVQAOGYNZNTIA-CLLJXQQHSA-N

> <FORMULA>
C17H22N4O

> <MOLECULAR_WEIGHT>
298.3828

> <EXACT_MASS>
298.179361346

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.3152261759528

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide

> <ALOGPS_LOGP>
2.57

> <JCHEM_LOGP>
1.3349142853794491

> <ALOGPS_LOGS>
-3.67

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
15.650106458151413

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.249547476205642

> <JCHEM_PKA_STRONGEST_BASIC>
8.976393439732629

> <JCHEM_POLAR_SURFACE_AREA>
61.02

> <JCHEM_REFRACTIVITY>
86.60969999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0061061
     RDKit          3D
9'-desmethylgranisetron
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1758   -2.1153    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -1.1872    0.2807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361   -0.7014   -1.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8121    0.4829   -1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892    1.5381   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0905    0.8718    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0090   -0.1727    1.2651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6391    0.4227    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -0.1803    0.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4613    0.4619   -0.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -0.1689    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.3678    0.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.5397   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    1.8397   -0.3899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315    2.1159   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    1.0311   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5225    0.8139   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9783   -0.4381    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0956   -1.4752    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.1949    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399    0.0409    0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.2385   -1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -2.5993    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433   -2.9279   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -1.6880    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -1.4996   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.9573   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432    0.2008   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8230    2.0402   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    2.2866   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0466    0.3235    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886    1.5754    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -0.6342    2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6549    1.5201    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    0.1271    2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -1.2490    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.4864   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8410    3.0561   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2602    1.5734   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319   -0.6848    0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4680   -2.4568    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -1.9666    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.0408   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6817   -1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
  7  2  1  0
 21 13  1  0
 22  3  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  1
 10 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 22 44  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       3.978   1.101   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.960  -2.720   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.918  -3.926   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.219  -2.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.456  -1.042   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.161  -1.747   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.437  -2.947   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.353  -5.358   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.286  -2.820   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.041  -3.569   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.517  -3.904   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.172  -1.040   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.953  -1.727   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.872  -4.380   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.830  -5.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.429  -4.918   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.145  -4.068   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       0.233  -4.754   0.000  0.00  0.00           N+0
HETATM   19  N   UNK     0      -3.979  -6.869   0.000  0.00  0.00           N+0
HETATM   20  N   UNK     0      -2.496  -6.457   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0       3.198  -0.227   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      -1.240  -2.531   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       2.777   0.376   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0       4.010  -0.606   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2    3    7                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4   12                                                       
CONECT    6    4   13                                                       
CONECT    7    2   14                                                       
CONECT    8    3   15                                                       
CONECT    9   11   12                                                       
CONECT   10   11   13                                                       
CONECT   11    9   10   18                                                  
CONECT   12    5    9   21   23                                             
CONECT   13    6   10   21   24                                             
CONECT   14    7   15   16                                                  
CONECT   15    8   14   19                                                  
CONECT   16   14   17   20                                                  
CONECT   17   16   18   22                                                  
CONECT   18   11   17                                                       
CONECT   19   15   20                                                       
CONECT   20   16   19                                                       
CONECT   21    1   12   13                                                  
CONECT   22   17                                                            
CONECT   23   12                                                            
CONECT   24   13                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0061061
HETATM    1  C1  UNL     1      -4.176  -2.115   0.444  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.108  -1.187   0.281  1.00  0.00           N  
HETATM    3  C2  UNL     1      -2.936  -0.701  -1.063  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.812   0.483  -1.381  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.789   1.538  -0.307  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.091   0.872   1.018  1.00  0.00           C  
HETATM    7  C6  UNL     1      -3.009  -0.173   1.265  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.639   0.423   1.249  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.804  -0.180   0.158  1.00  0.00           C  
HETATM   10  N2  UNL     1       0.461   0.462  -0.016  1.00  0.00           N  
HETATM   11  C9  UNL     1       1.711  -0.169   0.167  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.744  -1.368   0.504  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.957   0.540  -0.026  1.00  0.00           C  
HETATM   14  N3  UNL     1       3.142   1.840  -0.390  1.00  0.00           N  
HETATM   15  N4  UNL     1       4.432   2.116  -0.461  1.00  0.00           N  
HETATM   16  C11 UNL     1       5.162   1.031  -0.153  1.00  0.00           C  
HETATM   17  C12 UNL     1       6.522   0.814  -0.085  1.00  0.00           C  
HETATM   18  C13 UNL     1       6.978  -0.438   0.269  1.00  0.00           C  
HETATM   19  C14 UNL     1       6.096  -1.475   0.556  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.748  -1.195   0.471  1.00  0.00           C  
HETATM   21  C16 UNL     1       4.240   0.041   0.121  1.00  0.00           C  
HETATM   22  C17 UNL     1      -1.497  -0.239  -1.171  1.00  0.00           C  
HETATM   23  H1  UNL     1      -4.064  -2.599   1.441  1.00  0.00           H  
HETATM   24  H2  UNL     1      -4.043  -2.928  -0.308  1.00  0.00           H  
HETATM   25  H3  UNL     1      -5.185  -1.688   0.325  1.00  0.00           H  
HETATM   26  H4  UNL     1      -3.190  -1.500  -1.775  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.365   0.957  -2.304  1.00  0.00           H  
HETATM   28  H6  UNL     1      -4.843   0.201  -1.661  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.823   2.040  -0.339  1.00  0.00           H  
HETATM   30  H8  UNL     1      -4.564   2.287  -0.567  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.047   0.323   0.896  1.00  0.00           H  
HETATM   32  H10 UNL     1      -4.189   1.575   1.848  1.00  0.00           H  
HETATM   33  H11 UNL     1      -3.274  -0.634   2.258  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.655   1.520   1.252  1.00  0.00           H  
HETATM   35  H13 UNL     1      -1.147   0.127   2.222  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.606  -1.249   0.459  1.00  0.00           H  
HETATM   37  H15 UNL     1       0.416   1.486  -0.304  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.841   3.056  -0.723  1.00  0.00           H  
HETATM   39  H17 UNL     1       7.260   1.573  -0.295  1.00  0.00           H  
HETATM   40  H18 UNL     1       8.032  -0.685   0.344  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.468  -2.457   0.834  1.00  0.00           H  
HETATM   42  H20 UNL     1       4.009  -1.967   0.684  1.00  0.00           H  
HETATM   43  H21 UNL     1      -0.971  -1.041  -1.767  1.00  0.00           H  
HETATM   44  H22 UNL     1      -1.393   0.682  -1.763  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    7
CONECT    3    4   22   26
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8   33
CONECT    8    9   34   35
CONECT    9   10   22   36
CONECT   10   11   37
CONECT   11   12   12   13
CONECT   13   14   14   21
CONECT   14   15
CONECT   15   16   38
CONECT   16   17   17   21
CONECT   17   18   39
CONECT   18   19   19   40
CONECT   19   20   41
CONECT   20   21   21   42
CONECT   22   43   44
END

HMDB0061061
     RDKit          3D
9'-desmethylgranisetron
 44 47  0  0  0  0  0  0  0  0999 V2000
   -4.1758   -2.1153    0.4438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1083   -1.1872    0.2807 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9361   -0.7014   -1.0627 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.8121    0.4829   -1.3814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7892    1.5381   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0905    0.8718    1.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0090   -0.1727    1.2651 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6391    0.4227    1.2492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8042   -0.1803    0.1579 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4613    0.4619   -0.0163 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7108   -0.1689    0.1673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7444   -1.3678    0.5044 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.5397   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1418    1.8397   -0.3899 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4315    2.1159   -0.4611 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625    1.0311   -0.1526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5225    0.8139   -0.0848 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9783   -0.4381    0.2692 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0956   -1.4752    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7481   -1.1949    0.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2399    0.0409    0.1210 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4974   -0.2385   -1.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0637   -2.5993    1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433   -2.9279   -0.3080 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -1.6880    0.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1896   -1.4996   -1.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3655    0.9573   -2.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8432    0.2008   -1.6615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8230    2.0402   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5639    2.2866   -0.5666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0466    0.3235    0.8965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1886    1.5754    1.8483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2744   -0.6342    2.2579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6549    1.5201    1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1469    0.1271    2.2221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6063   -1.2490    0.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4161    1.4864   -0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8410    3.0561   -0.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2602    1.5734   -0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0319   -0.6848    0.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4680   -2.4568    0.8338 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0091   -1.9666    0.6838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9705   -1.0408   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3928    0.6817   -1.7625 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
  9 22  1  0
  7  2  1  0
 21 13  1  0
 22  3  1  0
 21 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  6
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  1
  8 34  1  0
  8 35  1  0
  9 36  1  1
 10 37  1  0
 15 38  1  0
 17 39  1  0
 18 40  1  0
 19 41  1  0
 20 42  1  0
 22 43  1  0
 22 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₂₂N₄O

Average Molecular Weight

298.3828

Monoisotopic Molecular Weight

298.179361346

IUPAC Name

N-[(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide

Traditional Name

N-[(1R,3r,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide

CAS Registry Number

Not Available

SMILES

[H][C@]12CCC[C@]([H])(C[C@@H](C1)NC(=O)C1=NNC3=CC=CC=C13)N2C

InChI Identifier

InChI=1S/C17H22N4O/c1-21-12-5-4-6-13(21)10-11(9-12)18-17(22)16-14-7-2-3-8-15(14)19-20-16/h2-3,7-8,11-13H,4-6,9-10H2,1H3,(H,18,22)(H,19,20)/t11-,12+,13-

InChI Key

GHVQAOGYNZNTIA-CLLJXQQHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indazole-3-carboxamides. These are aromatic compounds containing an indazole ring system that is substituted at the 3-position with a carboxamide group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrazoles

Sub Class

Indazoles

Direct Parent

Indazole-3-carboxamides

Alternative Parents

Substituents

Indazole-3-carboxamide
2-heteroaryl carboxamide
Pyrazole-5-carboxamide
Piperidine
Benzenoid
Azole
Heteroaromatic compound
Pyrazole
Amino acid or derivatives
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Amine
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Kidney (HMDB: HMDB0061061)
Liver (HMDB: HMDB0061061)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0061061)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0061061)

Cellular substructure

Cytoplasm (HMDB: HMDB0061061)

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	0.064 g/L	ALOGPS
logP	2.57	ALOGPS
logP	1.33	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	9.25	ChemAxon
pKa (Strongest Basic)	8.98	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	61.02 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	86.61 m³·mol⁻¹	ChemAxon
Polarizability	33.32 Å³	ChemAxon
Number of Rings	4	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]+	174.306	31661259
DarkChem	[M-H]-	168.531	31661259
DeepCCS	[M-2H]-	208.765	30932474
DeepCCS	[M+Na]+	183.591	30932474
AllCCS	[M+H]+	174.3	32859911
AllCCS	[M+H-H2O]+	171.1	32859911
AllCCS	[M+NH4]+	177.2	32859911
AllCCS	[M+Na]+	178.0	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	174.8	32859911
AllCCS	[M+HCOO]-	174.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9'-desmethylgranisetron	[H][C@]12CCC[C@]([H])(C[C@@H](C1)NC(=O)C1=NNC3=CC=CC=C13)N2C	3488.3	Standard polar	33892256
9'-desmethylgranisetron	[H][C@]12CCC[C@]([H])(C[C@@H](C1)NC(=O)C1=NNC3=CC=CC=C13)N2C	2914.0	Standard non polar	33892256
9'-desmethylgranisetron	[H][C@]12CCC[C@]([H])(C[C@@H](C1)NC(=O)C1=NNC3=CC=CC=C13)N2C	3046.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9'-desmethylgranisetron,1TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C)C2	2819.1	Semi standard non polar	33892256
9'-desmethylgranisetron,1TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C)C2	2650.3	Standard non polar	33892256
9'-desmethylgranisetron,1TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C)C2	3800.1	Standard polar	33892256
9'-desmethylgranisetron,1TMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)C2	2891.4	Semi standard non polar	33892256
9'-desmethylgranisetron,1TMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)C2	2672.9	Standard non polar	33892256
9'-desmethylgranisetron,1TMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)C2	3874.0	Standard polar	33892256
9'-desmethylgranisetron,2TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)[Si](C)(C)C)C2	2828.3	Semi standard non polar	33892256
9'-desmethylgranisetron,2TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)[Si](C)(C)C)C2	2685.6	Standard non polar	33892256
9'-desmethylgranisetron,2TMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C)C3=CC=CC=C13)[Si](C)(C)C)C2	3675.7	Standard polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3070.9	Semi standard non polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	2880.5	Standard non polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=N[NH]C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3883.3	Standard polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)C2	3055.0	Semi standard non polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)C2	2887.8	Standard non polar	33892256
9'-desmethylgranisetron,1TBDMS,isomer #2	CN1[C@H]2CCC[C@@H]1C[C@H](NC(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)C2	3936.5	Standard polar	33892256
9'-desmethylgranisetron,2TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3202.4	Semi standard non polar	33892256
9'-desmethylgranisetron,2TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3109.1	Standard non polar	33892256
9'-desmethylgranisetron,2TBDMS,isomer #1	CN1[C@H]2CCC[C@@H]1C[C@H](N(C(=O)C1=NN([Si](C)(C)C(C)(C)C)C3=CC=CC=C13)[Si](C)(C)C(C)(C)C)C2	3747.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-desmethylgranisetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-7970000000-2bb142aca5e807106f37	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9'-desmethylgranisetron 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 - 9'-desmethylgranisetron 10V, Positive-QTOF	splash10-0002-0490000000-d18f11e6c320f69e7e30	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 20V, Positive-QTOF	splash10-052k-0920000000-40706f954a1b6224e718	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 40V, Positive-QTOF	splash10-000j-2900000000-779296672333c6123513	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 10V, Negative-QTOF	splash10-0002-0390000000-c426a68d7880ed3ddd19	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 20V, Negative-QTOF	splash10-0uxs-0920000000-0f3aea5536885a0e2e90	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 40V, Negative-QTOF	splash10-0f7c-1900000000-2a7d21ad07214ac5d378	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 10V, Positive-QTOF	splash10-0002-0090000000-511d32507fde56d9249e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 20V, Positive-QTOF	splash10-00kb-0090000000-a9813826b521a5525133	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 40V, Positive-QTOF	splash10-014j-1950000000-83a10bfc078216276fa5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 10V, Negative-QTOF	splash10-0002-0090000000-524104d6853e23d834e0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 20V, Negative-QTOF	splash10-0002-1290000000-f16496c77ccb2f438d99	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9'-desmethylgranisetron 40V, Negative-QTOF	splash10-014i-4910000000-82e40b550b6544ba411a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

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

Not Available

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 9'-desmethylgranisetron (HMDB0061061)

MOL for HMDB0061061 (9'-desmethylgranisetron)

3D MOL for HMDB0061061 (9'-desmethylgranisetron)

3D SDF for HMDB0061061 (9'-desmethylgranisetron)

3D-SDF for HMDB0061061 (9'-desmethylgranisetron)

PDB for HMDB0061061 (9'-desmethylgranisetron)

3D PDB for HMDB0061061 (9'-desmethylgranisetron)

SMILES for HMDB0061061 (9'-desmethylgranisetron)

INCHI for HMDB0061061 (9'-desmethylgranisetron)

Structure for HMDB0061061 (9'-desmethylgranisetron)

3D Structure for HMDB0061061 (9'-desmethylgranisetron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra