Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (4) Show 4 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:50 UTC

Update Date

2022-03-07 02:51:46 UTC

HMDB ID

HMDB0014895

Secondary Accession Numbers

HMDB14895

Metabolite Identification

Common Name

Dolasetron

Description

Dolasetron is an antinauseant and antiemetic agent indicated for the prevention of nausea and vomiting associated with moderately-emetogenic cancer chemotherapy and for the prevention of postoperative nausea and vomiting. Dolasetron is a highly specific and selective serotonin 5-HT3 receptor antagonist. This drug has not shown to have activity at other known serotonin receptors, and has low affinity for dopamine receptors.

Structure

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

757
  Mrv0541 02231214592D          

 25 29  0  0  1  0            999 V2000
    5.4924    0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599    2.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736   -0.4950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    1.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5181   -0.7704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    2.2019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3786    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    2.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4924   -0.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2110   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -1.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1086   -1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664   -2.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0001   -2.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8122   -2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7497    2.5339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 16  1  0  0  0  0
  2 15  2  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 14  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 25  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END

HMDB0014895
     RDKit          3D
Dolasetron
 44 48  0  0  0  0  0  0  0  0999 V2000
    1.4715   -0.9547   -0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578   -0.0701   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501    0.5311    0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    0.1332    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4637   -0.3807    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634   -0.3295    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989   -1.4683    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2176   -0.8724   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564    0.0619   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.1768   -0.6559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4052    1.3437   -0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.9707    0.6891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646    0.9912    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0808   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4394   -0.2927   -0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.3057    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    1.2572    1.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3128    1.3278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973    0.4345    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4973    0.1146    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726   -0.8530   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.5066   -1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -1.1870   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730   -0.2242   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.6413   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.4622    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    0.1239    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975   -0.4884    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915   -2.0894   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1318   -2.1419    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -1.7048   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6788    0.4726   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -0.5270   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    2.1640   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    1.4223   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.2549    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410    0.8610    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1509    1.9965    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.8381    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917    1.9432    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3092    0.6231    0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7971   -1.1285   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -2.2640   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -1.6653   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  4  1  0
 24 16  1  0
 12  6  1  0
 24 19  1  0
 14  8  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

757
  Mrv0541 02231214592D          

 25 29  0  0  1  0            999 V2000
    5.4924    0.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6599    2.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7736   -0.4950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    1.8562    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5181   -0.7704    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5761    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    2.2019    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3786    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1748    0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7735    1.1649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9774    2.2019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3786    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4924   -0.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2110   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2966   -1.3155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9644   -0.1587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1086   -1.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7423   -1.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3664   -2.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0001   -2.7222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8122   -2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7497    2.5339    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  1 16  1  0  0  0  0
  2 15  2  0  0  0  0
  3 16  2  0  0  0  0
  4  6  1  0  0  0  0
  4  7  1  0  0  0  0
  4 14  1  0  0  0  0
  5 19  1  0  0  0  0
  5 20  1  0  0  0  0
  6  9  1  0  0  0  0
  6 11  1  0  0  0  0
  7 10  1  0  0  0  0
  7 12  1  0  0  0  0
  7 25  1  1  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 15  1  0  0  0  0
 11 13  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 20 22  2  0  0  0  0
 21 23  1  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014895

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C19H20N2O3/c22-18-10-21-12-5-11(18)6-13(21)8-14(7-12)24-19(23)16-9-20-17-4-2-1-3-15(16)17/h1-4,9,11-14,20H,5-8,10H2/t11?,12-,13?,14?/m1/s1

> <INCHI_KEY>
UKTAZPQNNNJVKR-DBBXXEFVSA-N

> <FORMULA>
C19H20N2O3

> <MOLECULAR_WEIGHT>
324.3737

> <EXACT_MASS>
324.147392516

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.68876326112222

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-10-oxo-8-azatricyclo[5.3.1.0³,⁸]undecan-5-yl 1H-indole-3-carboxylate

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.3258902303333335

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.246578940288476

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.182265701749415

> <JCHEM_PKA_STRONGEST_BASIC>
6.8835551250295275

> <JCHEM_POLAR_SURFACE_AREA>
62.400000000000006

> <JCHEM_REFRACTIVITY>
89.33520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dolasetron

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0014895
     RDKit          3D
Dolasetron
 44 48  0  0  0  0  0  0  0  0999 V2000
    1.4715   -0.9547   -0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578   -0.0701   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501    0.5311    0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    0.1332    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4637   -0.3807    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634   -0.3295    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989   -1.4683    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2176   -0.8724   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564    0.0619   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.1768   -0.6559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4052    1.3437   -0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.9707    0.6891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646    0.9912    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0808   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4394   -0.2927   -0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.3057    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    1.2572    1.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3128    1.3278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973    0.4345    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4973    0.1146    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726   -0.8530   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.5066   -1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -1.1870   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730   -0.2242   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.6413   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.4622    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    0.1239    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975   -0.4884    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915   -2.0894   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1318   -2.1419    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -1.7048   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6788    0.4726   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -0.5270   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    2.1640   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    1.4223   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.2549    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410    0.8610    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1509    1.9965    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.8381    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917    1.9432    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3092    0.6231    0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7971   -1.1285   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -2.2640   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -1.6653   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  4  1  0
 24 16  1  0
 12  6  1  0
 24 19  1  0
 14  8  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 757                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      10.252   1.400   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.098   4.239   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       8.911  -0.924   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0       6.675   3.465   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      14.034  -1.438   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.675   2.175   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.793   4.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.440   2.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.558   1.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.793   5.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.793   1.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.911   3.465   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.911   2.175   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.558   4.110   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.440   3.465   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.252  -0.149   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.594  -0.924   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.754  -2.456   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.000  -0.296   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      13.269  -2.775   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.719  -3.609   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      13.751  -4.248   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.200  -5.081   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.716  -5.401   0.000  0.00  0.00           C+0
HETATM   25  H   UNK     0       8.866   4.730   0.000  0.00  0.00           H+0
CONECT    1   13   16                                                       
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4    6    7   14                                                  
CONECT    5   19   20                                                       
CONECT    6    4    9   11                                                  
CONECT    7    4   10   12   25                                             
CONECT    8    9   10   15                                                  
CONECT    9    6    8                                                       
CONECT   10    7    8                                                       
CONECT   11    6   13                                                       
CONECT   12    7   13                                                       
CONECT   13    1   11   12                                                  
CONECT   14    4   15                                                       
CONECT   15    2    8   14                                                  
CONECT   16    1    3   17                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   20   21                                                  
CONECT   19    5   17                                                       
CONECT   20    5   18   22                                                  
CONECT   21   18   23                                                       
CONECT   22   20   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
CONECT   25    7                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

COMPND    HMDB0014895
HETATM    1  O1  UNL     1       1.471  -0.955  -0.959  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.658  -0.070  -0.087  1.00  0.00           C  
HETATM    3  O2  UNL     1       0.550   0.531   0.482  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.739   0.133   0.066  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.464  -0.381   1.286  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.963  -0.330   1.126  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.399  -1.468   0.264  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.218  -0.872  -0.895  1.00  0.00           C  
HETATM    9  C7  UNL     1      -3.256   0.062  -1.606  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.910   1.177  -0.656  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.405   1.344  -0.542  1.00  0.00           C  
HETATM   12  N1  UNL     1      -3.408   0.971   0.689  1.00  0.00           N  
HETATM   13  C10 UNL     1      -4.865   0.991   0.692  1.00  0.00           C  
HETATM   14  C11 UNL     1      -5.281  -0.081  -0.239  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.439  -0.293  -0.448  1.00  0.00           O  
HETATM   16  C12 UNL     1       3.001   0.306   0.308  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.320   1.257   1.248  1.00  0.00           C  
HETATM   18  N2  UNL     1       4.644   1.313   1.328  1.00  0.00           N  
HETATM   19  C14 UNL     1       5.197   0.435   0.477  1.00  0.00           C  
HETATM   20  C15 UNL     1       6.497   0.115   0.188  1.00  0.00           C  
HETATM   21  C16 UNL     1       6.773  -0.853  -0.757  1.00  0.00           C  
HETATM   22  C17 UNL     1       5.743  -1.507  -1.418  1.00  0.00           C  
HETATM   23  C18 UNL     1       4.445  -1.187  -1.129  1.00  0.00           C  
HETATM   24  C19 UNL     1       4.173  -0.224  -0.190  1.00  0.00           C  
HETATM   25  H1  UNL     1      -0.656  -0.641  -0.692  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.189  -1.462   1.391  1.00  0.00           H  
HETATM   27  H3  UNL     1      -1.157   0.124   2.205  1.00  0.00           H  
HETATM   28  H4  UNL     1      -3.398  -0.488   2.145  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.591  -2.089  -0.131  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.132  -2.142   0.797  1.00  0.00           H  
HETATM   31  H7  UNL     1      -4.563  -1.705  -1.501  1.00  0.00           H  
HETATM   32  H8  UNL     1      -3.679   0.473  -2.538  1.00  0.00           H  
HETATM   33  H9  UNL     1      -2.349  -0.527  -1.825  1.00  0.00           H  
HETATM   34  H10 UNL     1      -3.298   2.164  -1.008  1.00  0.00           H  
HETATM   35  H11 UNL     1      -1.004   1.422  -1.589  1.00  0.00           H  
HETATM   36  H12 UNL     1      -1.184   2.255   0.037  1.00  0.00           H  
HETATM   37  H13 UNL     1      -5.241   0.861   1.709  1.00  0.00           H  
HETATM   38  H14 UNL     1      -5.151   1.996   0.288  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.589   1.838   1.804  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.192   1.943   1.957  1.00  0.00           H  
HETATM   41  H17 UNL     1       7.309   0.623   0.702  1.00  0.00           H  
HETATM   42  H18 UNL     1       7.797  -1.129  -1.007  1.00  0.00           H  
HETATM   43  H19 UNL     1       5.968  -2.264  -2.157  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.612  -1.665  -1.615  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4
CONECT    4    5   11   25
CONECT    5    6   26   27
CONECT    6    7   12   28
CONECT    7    8   29   30
CONECT    8    9   14   31
CONECT    9   10   32   33
CONECT   10   11   12   34
CONECT   11   35   36
CONECT   12   13
CONECT   13   14   37   38
CONECT   14   15   15
CONECT   16   17   17   24
CONECT   17   18   39
CONECT   18   19   40
CONECT   19   20   20   24
CONECT   20   21   41
CONECT   21   22   22   42
CONECT   22   23   43
CONECT   23   24   24   44
END

HMDB0014895
     RDKit          3D
Dolasetron
 44 48  0  0  0  0  0  0  0  0999 V2000
    1.4715   -0.9547   -0.9589 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6578   -0.0701   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5501    0.5311    0.4816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7388    0.1332    0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4637   -0.3807    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9634   -0.3295    1.1262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3989   -1.4683    0.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2176   -0.8724   -0.8947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2564    0.0619   -1.6059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9098    1.1768   -0.6559 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4052    1.3437   -0.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4083    0.9707    0.6891 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8646    0.9912    0.6925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2813   -0.0808   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4394   -0.2927   -0.4476 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0013    0.3057    0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3202    1.2572    1.2478 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6441    1.3128    1.3278 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973    0.4345    0.4765 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4973    0.1146    0.1875 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7726   -0.8530   -0.7568 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7428   -1.5066   -1.4180 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4454   -1.1870   -1.1294 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1730   -0.2242   -0.1897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6564   -0.6413   -0.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1886   -1.4622    1.3912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570    0.1239    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3975   -0.4884    2.1452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5915   -2.0894   -0.1312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1318   -2.1419    0.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5632   -1.7048   -1.5006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6788    0.4726   -2.5376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3491   -0.5270   -1.8248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2979    2.1640   -1.0079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0042    1.4223   -1.5893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1842    2.2549    0.0372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2410    0.8610    1.7088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1509    1.9965    0.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5885    1.8381    1.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917    1.9432    1.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3092    0.6231    0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7971   -1.1285   -1.0074 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9676   -2.2640   -2.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117   -1.6653   -1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  2 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 11  4  1  0
 24 16  1  0
 12  6  1  0
 24 19  1  0
 14  8  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  6
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 17 39  1  0
 18 40  1  0
 20 41  1  0
 21 42  1  0
 22 43  1  0
 23 44  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anzemet	HMDB
MDL 73147Ef	HMDB
MDL-73147Ef	HMDB
MDL 73,147Ef	HMDB
Octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl 1H-indole-3-carboxylate	HMDB
Dolasetron mesylate	HMDB
1H-Indole-3-carboxylic acid-trans-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester methanesulfonate	HMDB
Dolasetron mesilate monohydrate	MeSH
1H-Indole-3-carboxylic acid, (6R,9as)-octahydro-3-oxo-2,6-methano-2H-quinolizin-8-yl ester, rel-, methanesulfonate, hydrate (1:1:1)	MeSH
Dolasetron mesylate monohydrate	MeSH
Indole-3-carboxylic acid, ester with (8R)-hexahydro-8-hydroxy-2,6-methano-2H-quinolizin-3(4H)-one	MeSH
(3R)-10-oxo-8-Azatricyclo[5.3.1.0³,⁸]undecan-5-yl 1H-indole-3-carboxylic acid	Generator
Dolasetron	MeSH
(3R)-10-oxo-8-Azatricyclo[5.3.1.0,]undecan-5-yl 1H-indole-3-carboxylic acid	Generator

Chemical Formula

C₁₉H₂₀N₂O₃

Average Molecular Weight

324.3737

Monoisotopic Molecular Weight

324.147392516

IUPAC Name

(3R)-10-oxo-8-azatricyclo[5.3.1.0³,⁸]undecan-5-yl 1H-indole-3-carboxylate

Traditional Name

dolasetron

CAS Registry Number

115956-12-2

SMILES

[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C19H20N2O3/c22-18-10-21-12-5-11(18)6-13(21)8-14(7-12)24-19(23)16-9-20-17-4-2-1-3-15(16)17/h1-4,9,11-14,20H,5-8,10H2/t11?,12-,13?,14?/m1/s1

InChI Key

UKTAZPQNNNJVKR-DBBXXEFVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolecarboxylic acids and derivatives. Indolecarboxylic acids and derivatives are compounds containing a carboxylic acid group (or a derivative thereof) linked to an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolecarboxylic acids and derivatives

Direct Parent

Indolecarboxylic acids and derivatives

Alternative Parents

Substituents

Indolecarboxylic acid derivative
Quinolizidine
Indole
Quinuclidone
Pyrrole-3-carboxylic acid or derivatives
Quinuclidine
Piperidinone
Piperidine
Substituted pyrrole
Benzenoid
Vinylogous amide
Pyrrole
Heteroaromatic compound
Tertiary amine
Tertiary aliphatic amine
Carboxylic acid ester
Ketone
Amino acid or derivatives
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Azacycle
Amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Membrane (HMDB: HMDB0014895)

Source

Exogenous

Exogenous (HMDB: HMDB0014895)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	278 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.26 g/L	Not Available
LogP	2.1	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.26 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.33	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.18	ChemAxon
pKa (Strongest Basic)	6.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	62.4 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	89.34 m³·mol⁻¹	ChemAxon
Polarizability	33.69 Å³	ChemAxon
Number of Rings	5	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]+	176.344	31661259
DarkChem	[M-H]-	173.966	31661259
DeepCCS	[M-2H]-	210.486	30932474
DeepCCS	[M+Na]+	185.839	30932474
AllCCS	[M+H]+	178.7	32859911
AllCCS	[M+H-H2O]+	175.8	32859911
AllCCS	[M+NH4]+	181.4	32859911
AllCCS	[M+Na]+	182.1	32859911
AllCCS	[M-H]-	180.5	32859911
AllCCS	[M+Na-2H]-	180.0	32859911
AllCCS	[M+HCOO]-	179.6	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.	5.53 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6565 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1802.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	211.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	123.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	360.7 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	362.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	343.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	773.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	371.7 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	1213.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	243.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	321.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	361.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	280.4 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	126.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dolasetron	[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12	3800.8	Standard polar	33892256
Dolasetron	[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12	2849.1	Standard non polar	33892256
Dolasetron	[H][C@]12CC(CC3CC(C1)C(=O)CN23)OC(=O)C1=CNC2=CC=CC=C12	3437.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dolasetron,1TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	3178.6	Semi standard non polar	33892256
Dolasetron,1TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	2900.9	Standard non polar	33892256
Dolasetron,1TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	3995.2	Standard polar	33892256
Dolasetron,1TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	3200.5	Semi standard non polar	33892256
Dolasetron,1TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	2906.5	Standard non polar	33892256
Dolasetron,1TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	4080.1	Standard polar	33892256
Dolasetron,1TMS,isomer #3	C[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	3102.6	Semi standard non polar	33892256
Dolasetron,1TMS,isomer #3	C[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	2992.7	Standard non polar	33892256
Dolasetron,1TMS,isomer #3	C[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	4021.7	Standard polar	33892256
Dolasetron,2TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	3115.3	Semi standard non polar	33892256
Dolasetron,2TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	2957.5	Standard non polar	33892256
Dolasetron,2TMS,isomer #1	C[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	3852.5	Standard polar	33892256
Dolasetron,2TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	3169.7	Semi standard non polar	33892256
Dolasetron,2TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	2905.6	Standard non polar	33892256
Dolasetron,2TMS,isomer #2	C[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	3962.0	Standard polar	33892256
Dolasetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	3389.5	Semi standard non polar	33892256
Dolasetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	3084.0	Standard non polar	33892256
Dolasetron,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@@H](C2)N3C1	4090.3	Standard polar	33892256
Dolasetron,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	3431.5	Semi standard non polar	33892256
Dolasetron,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	3053.6	Standard non polar	33892256
Dolasetron,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=C[NH]C5=CC=CC=C45)C[C@H]2CC1C3	4177.1	Standard polar	33892256
Dolasetron,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	3303.0	Semi standard non polar	33892256
Dolasetron,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	3202.1	Standard non polar	33892256
Dolasetron,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N1C=C(C(=O)OC2CC3CC4C[C@H](C2)N3CC4=O)C2=CC=CC=C21	4105.3	Standard polar	33892256
Dolasetron,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	3491.8	Semi standard non polar	33892256
Dolasetron,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	3269.9	Standard non polar	33892256
Dolasetron,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C2CC3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@@H](C2)N3C1	3950.4	Standard polar	33892256
Dolasetron,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	3587.0	Semi standard non polar	33892256
Dolasetron,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	3197.2	Standard non polar	33892256
Dolasetron,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CN2C3CC(OC(=O)C4=CN([Si](C)(C)C(C)(C)C)C5=CC=CC=C45)C[C@H]2CC1C3	4055.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dolasetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-1900000000-8dcd9035e77addcb92c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dolasetron 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 - Dolasetron 10V, Positive-QTOF	splash10-004i-0809000000-e543237d634e768bf190	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 20V, Positive-QTOF	splash10-03dl-0901000000-d6386713d3df49c9837e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 40V, Positive-QTOF	splash10-00l6-0900000000-0b1c6b04e96536805498	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 10V, Negative-QTOF	splash10-00di-0509000000-085a8f6a1ddf99d931fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 20V, Negative-QTOF	splash10-01b9-0903000000-3363bde3d5011e6d4a88	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 40V, Negative-QTOF	splash10-014i-0900000000-49ee7a167d32200b182c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 10V, Positive-QTOF	splash10-004i-0009000000-9b54b47c162811e47733	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 20V, Positive-QTOF	splash10-004i-0409000000-dcf423a8abd27c382925	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 40V, Positive-QTOF	splash10-014l-1900000000-b5bcc02270654ef46e8e	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 10V, Negative-QTOF	splash10-00di-0009000000-ffc9bb102611a33bd213	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 20V, Negative-QTOF	splash10-00di-0809000000-00ad969880df21e26b60	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dolasetron 40V, Negative-QTOF	splash10-014i-0902000000-f4b49f170c3bb0df26cd	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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 DB00757	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00757	21059682	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

54666

KEGG Compound ID

C07866

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dolasetron

METLIN ID

Not Available

PubChem Compound

60654

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

Balfour JA, Goa KL: Dolasetron. A review of its pharmacology and therapeutic potential in the management of nausea and vomiting induced by chemotherapy, radiotherapy or surgery. Drugs. 1997 Aug;54(2):273-98. [PubMed:9257083 ]
Gregory RE, Ettinger DS: 5-HT3 receptor antagonists for the prevention of chemotherapy-induced nausea and vomiting. A comparison of their pharmacology and clinical efficacy. Drugs. 1998 Feb;55(2):173-89. [PubMed:9506240 ]
Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [PubMed:15740177 ]

Enzymes

Enzyme Details

1. Cytochrome P450 3A4

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:: CYP3A4
Uniprot ID:: P08684
Molecular weight:: 57255.585

References

Sanwald P, David M, Dow J: Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of dolasetron. Comparison with other indole-containing 5-HT3 antagonists. Drug Metab Dispos. 1996 May;24(5):602-9. [PubMed:8723743 ]

Enzyme Details

2. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. 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

Janicki PK: Cytochrome P450 2D6 metabolism and 5-hydroxytryptamine type 3 receptor antagonists for postoperative nausea and vomiting. Med Sci Monit. 2005 Oct;11(10):RA322-8. Epub 2005 Sep 26. [PubMed:16192915 ]
Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Sanwald P, David M, Dow J: Characterization of the cytochrome P450 enzymes involved in the in vitro metabolism of dolasetron. Comparison with other indole-containing 5-HT3 antagonists. Drug Metab Dispos. 1996 May;24(5):602-9. [PubMed:8723743 ]

Enzyme Details

4. 5-hydroxytryptamine receptor 3A

General function:: Involved in extracellular ligand-gated ion channel activity
Specific function:: This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:: HTR3A
Uniprot ID:: P46098
Molecular weight:: 55279.8

References

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Conroy T, Cappelaere P, Fabbro M, Fauser AA, Splinter TA, Spielmann M, Schneider M, Chevallier B, Goupil A, Chauvergne J, et al.: Acute antiemetic efficacy and safety of dolasetron mesylate, a 5-HT3 antagonist, in cancer patients treated with cisplatin. European Dolasetron Study Group. Am J Clin Oncol. 1994 Apr;17(2):97-102. [PubMed:8141114 ]
Reith MK, Sproles GD, Cheng LK: Human metabolism of dolasetron mesylate, a 5-HT3 receptor antagonist. Drug Metab Dispos. 1995 Aug;23(8):806-12. [PubMed:7493546 ]
Eisenberg P, Figueroa-Vadillo J, Zamora R, Charu V, Hajdenberg J, Cartmell A, Macciocchi A, Grunberg S: Improved prevention of moderately emetogenic chemotherapy-induced nausea and vomiting with palonosetron, a pharmacologically novel 5-HT3 receptor antagonist: results of a phase III, single-dose trial versus dolasetron. Cancer. 2003 Dec 1;98(11):2473-82. [PubMed:14635083 ]
Monaca-Charley C, Stojkovic T, Duhamel A, De Seze J, Ferriby D, Vermersch P: Double-blind crossover study with dolasetron mesilate, a 5-HT3 receptor antagonist in cerebellar syndrome secondary to multiple sclerosis. J Neurol. 2003 Oct;250(10):1190-4. [PubMed:14586600 ]
Boeijinga PH, Galvan M, Baron BM, Dudley MW, Siegel BW, Slone AL: Characterization of the novel 5-HT3 antagonists MDL 73147EF (dolasetron mesilate) and MDL 74156 in NG108-15 neuroblastoma x glioma cells. Eur J Pharmacol. 1992 Aug 14;219(1):9-13. [PubMed:1397053 ]
Balfour JA, Goa KL: Dolasetron. A review of its pharmacology and therapeutic potential in the management of nausea and vomiting induced by chemotherapy, radiotherapy or surgery. Drugs. 1997 Aug;54(2):273-98. [PubMed:9257083 ]
Hui YF, Ignoffo RJ: Dolasetron. A new 5-hydroxytryptamine3 receptor antagonist. Cancer Pract. 1997 Sep-Oct;5(5):324-8. [PubMed:9341357 ]
Gregory RE, Ettinger DS: 5-HT3 receptor antagonists for the prevention of chemotherapy-induced nausea and vomiting. A comparison of their pharmacology and clinical efficacy. Drugs. 1998 Feb;55(2):173-89. [PubMed:9506240 ]
Gan TJ: Selective serotonin 5-HT3 receptor antagonists for postoperative nausea and vomiting: are they all the same? CNS Drugs. 2005;19(3):225-38. [PubMed:15740177 ]

Showing metabocard for Dolasetron (HMDB0014895)

MOL for HMDB0014895 (Dolasetron)

3D MOL for HMDB0014895 (Dolasetron)

3D SDF for HMDB0014895 (Dolasetron)

3D-SDF for HMDB0014895 (Dolasetron)

PDB for HMDB0014895 (Dolasetron)

3D PDB for HMDB0014895 (Dolasetron)

SMILES for HMDB0014895 (Dolasetron)

INCHI for HMDB0014895 (Dolasetron)

Structure for HMDB0014895 (Dolasetron)

3D Structure for HMDB0014895 (Dolasetron)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References