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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 23:01:06 UTC

Update Date

2022-11-23 22:29:22 UTC

HMDB ID

HMDB0259991

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Zatosetron

Description

5-chloro-2,2-dimethyl-N-{8-methyl-8-azabicyclo[3.2.1]octan-3-yl}-2,3-dihydro-1-benzofuran-7-carboximidic acid belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Based on a literature review very few articles have been published on 5-chloro-2,2-dimethyl-N-{8-methyl-8-azabicyclo[3.2.1]octan-3-yl}-2,3-dihydro-1-benzofuran-7-carboximidic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). Zatosetron is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Zatosetron is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259991
     RDKit          3D
ZATOSETRON
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.6062    0.3258    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.3077    0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073    1.4199    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7553    2.5986   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.9286   -1.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338    0.4623   -1.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.0768   -1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    0.8362   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.2044   -0.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1974   -1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.7667   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1303   -0.4038   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -0.4686   -2.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1751   -1.0978   -2.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929   -1.1173   -3.9988 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -1.6986   -1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -1.6634   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.0137   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891   -1.1601    0.9906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -1.2116    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367   -1.7462    3.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751    0.1022    1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0732   -2.2301    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0202    1.1107    0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0329   -0.4497   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9826    0.0388    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9602    1.3135   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.5920    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    3.1247   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    3.3703   -0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788    2.2933   -2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592    2.2307   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.1217   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913   -0.0703   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.0904   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080    1.7353   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.2396    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0045   -3.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5789   -2.2030   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -2.8343    3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301   -1.6334    3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -1.1789    4.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8652    2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.3015    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.0920    2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696   -3.2430    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386   -2.1481    1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    1.8913    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    0.1799    1.3032 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  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  8 24  1  0
  6  2  1  0
 18 12  1  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  0
 16 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END


  Mrv1652309122101012D          

 24 27  0  0  0  0            999 V2000
    1.1030   -0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6550    0.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3225    0.9947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0675    1.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    1.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876    0.9947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300    2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2425    3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0675    3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4800    3.9228    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0050    2.4938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075    1.7794    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4075    3.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2325    3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904    3.9516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947    4.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397    3.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0397    2.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3947    2.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5904    2.4650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6264    3.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4514    3.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2071   -0.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  2  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 15 21  1  0  0  0  0
 20 22  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259991

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1C2CCC1CC(C2)NC(=O)C1=CC(Cl)=CC2=C1OC(C)(C)C2

> <INCHI_IDENTIFIER>
InChI=1S/C19H25ClN2O2/c1-19(2)10-11-6-12(20)7-16(17(11)24-19)18(23)21-13-8-14-4-5-15(9-13)22(14)3/h6-7,13-15H,4-5,8-10H2,1-3H3,(H,21,23)

> <INCHI_KEY>
SPKBYQZELVEOLL-UHFFFAOYSA-N

> <FORMULA>
C19H25ClN2O2

> <MOLECULAR_WEIGHT>
348.87

> <EXACT_MASS>
348.1604558

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
38.59505647896941

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-chloro-2,2-dimethyl-N-{8-methyl-8-azabicyclo[3.2.1]octan-3-yl}-2,3-dihydro-1-benzofuran-7-carboxamide

> <ALOGPS_LOGP>
3.67

> <JCHEM_LOGP>
2.7831135196666668

> <ALOGPS_LOGS>
-4.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.838067244783627

> <JCHEM_PKA_STRONGEST_BASIC>
9.182732727185867

> <JCHEM_POLAR_SURFACE_AREA>
41.57

> <JCHEM_REFRACTIVITY>
96.00019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
zatosetron

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259991
     RDKit          3D
ZATOSETRON
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.6062    0.3258    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.3077    0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073    1.4199    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7553    2.5986   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.9286   -1.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338    0.4623   -1.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.0768   -1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    0.8362   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.2044   -0.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1974   -1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.7667   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1303   -0.4038   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -0.4686   -2.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1751   -1.0978   -2.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929   -1.1173   -3.9988 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -1.6986   -1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -1.6634   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.0137   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891   -1.1601    0.9906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -1.2116    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367   -1.7462    3.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751    0.1022    1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0732   -2.2301    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0202    1.1107    0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0329   -0.4497   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9826    0.0388    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9602    1.3135   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.5920    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    3.1247   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    3.3703   -0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788    2.2933   -2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592    2.2307   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.1217   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913   -0.0703   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.0904   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080    1.7353   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.2396    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0045   -3.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5789   -2.2030   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -2.8343    3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301   -1.6334    3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -1.1789    4.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8652    2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.3015    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.0920    2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696   -3.2430    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386   -2.1481    1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    1.8913    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    0.1799    1.3032 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  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  8 24  1  0
  6  2  1  0
 18 12  1  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  0
 16 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END

HEADER    PROTEIN                                 12-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-21         0                                  
HETATM    1  C   UNK     0       2.059  -0.193   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.089   0.952   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.335   1.857   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.859   3.321   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.319   3.321   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       1.844   1.857   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.549   4.655   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.319   5.989   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.859   5.989   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.629   4.655   0.000  0.00  0.00           C+0
HETATM   11 Cl   UNK     0       4.629   7.323   0.000  0.00  0.00          Cl+0
HETATM   12  C   UNK     0       0.009   4.655   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.761   3.321   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0      -0.761   5.989   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      -2.301   5.989   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.969   7.376   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.470   7.719   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.674   6.759   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.674   5.219   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.470   4.259   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.969   4.601   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      -4.903   5.989   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      -6.443   5.989   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.120  -0.193   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6   24                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    2                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    7   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   15                                                       
CONECT   22   20   17   23                                                  
CONECT   23   22                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0259991
HETATM    1  C1  UNL     1       5.606   0.326   0.110  1.00  0.00           C  
HETATM    2  N1  UNL     1       4.168   0.308   0.009  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.507   1.420   0.629  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.755   2.599  -0.286  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.812   1.929  -1.645  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.734   0.462  -1.386  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.328  -0.077  -1.494  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.438   0.836  -0.653  1.00  0.00           C  
HETATM    9  N2  UNL     1       0.129   0.204  -0.504  1.00  0.00           N  
HETATM   10  C8  UNL     1      -0.825   0.197  -1.541  1.00  0.00           C  
HETATM   11  O1  UNL     1      -0.489   0.767  -2.628  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.130  -0.404  -1.458  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.962  -0.469  -2.575  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.175  -1.098  -2.559  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -5.193  -1.117  -3.999  1.00  0.00          CL  
HETATM   16  C12 UNL     1      -4.624  -1.699  -1.434  1.00  0.00           C  
HETATM   17  C13 UNL     1      -3.854  -1.663  -0.308  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.605  -1.014  -0.318  1.00  0.00           C  
HETATM   19  O2  UNL     1      -2.089  -1.160   0.991  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.229  -1.212   1.868  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.937  -1.746   3.210  1.00  0.00           C  
HETATM   22  C17 UNL     1      -3.975   0.102   1.830  1.00  0.00           C  
HETATM   23  C18 UNL     1      -4.073  -2.230   1.068  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.020   1.111   0.674  1.00  0.00           C  
HETATM   25  H1  UNL     1       6.033  -0.450  -0.601  1.00  0.00           H  
HETATM   26  H2  UNL     1       5.983   0.039   1.087  1.00  0.00           H  
HETATM   27  H3  UNL     1       5.960   1.313  -0.253  1.00  0.00           H  
HETATM   28  H4  UNL     1       3.863   1.592   1.663  1.00  0.00           H  
HETATM   29  H5  UNL     1       4.713   3.125  -0.042  1.00  0.00           H  
HETATM   30  H6  UNL     1       2.967   3.370  -0.274  1.00  0.00           H  
HETATM   31  H7  UNL     1       2.979   2.293  -2.305  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.759   2.231  -2.122  1.00  0.00           H  
HETATM   33  H9  UNL     1       4.449  -0.122  -1.982  1.00  0.00           H  
HETATM   34  H10 UNL     1       1.991  -0.070  -2.509  1.00  0.00           H  
HETATM   35  H11 UNL     1       2.366  -1.090  -1.054  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.308   1.735  -1.270  1.00  0.00           H  
HETATM   37  H13 UNL     1      -0.067  -0.240   0.413  1.00  0.00           H  
HETATM   38  H14 UNL     1      -2.636  -0.005  -3.503  1.00  0.00           H  
HETATM   39  H15 UNL     1      -5.579  -2.203  -1.439  1.00  0.00           H  
HETATM   40  H16 UNL     1      -3.205  -2.834   3.296  1.00  0.00           H  
HETATM   41  H17 UNL     1      -1.830  -1.633   3.412  1.00  0.00           H  
HETATM   42  H18 UNL     1      -3.498  -1.179   4.006  1.00  0.00           H  
HETATM   43  H19 UNL     1      -3.376   0.865   2.313  1.00  0.00           H  
HETATM   44  H20 UNL     1      -4.170   0.301   0.759  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.946  -0.092   2.346  1.00  0.00           H  
HETATM   46  H22 UNL     1      -3.670  -3.243   1.175  1.00  0.00           H  
HETATM   47  H23 UNL     1      -5.139  -2.148   1.306  1.00  0.00           H  
HETATM   48  H24 UNL     1       1.446   1.891   1.203  1.00  0.00           H  
HETATM   49  H25 UNL     1       1.962   0.180   1.303  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    6
CONECT    3    4   24   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33
CONECT    7    8   34   35
CONECT    8    9   24   36
CONECT    9   10   37
CONECT   10   11   11   12
CONECT   12   13   13   18
CONECT   13   14   38
CONECT   14   15   16   16
CONECT   16   17   39
CONECT   17   18   18   23
CONECT   18   19
CONECT   19   20
CONECT   20   21   22   23
CONECT   21   40   41   42
CONECT   22   43   44   45
CONECT   23   46   47
CONECT   24   48   49
END

HMDB0259991
     RDKit          3D
ZATOSETRON
 49 52  0  0  0  0  0  0  0  0999 V2000
    5.6062    0.3258    0.1098 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1684    0.3077    0.0088 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5073    1.4199    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7553    2.5986   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8116    1.9286   -1.6451 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7338    0.4623   -1.3860 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3281   -0.0768   -1.4945 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    0.8362   -0.6529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290    0.2044   -0.5045 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247    0.1974   -1.5413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4894    0.7667   -2.6280 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1303   -0.4038   -1.4576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9622   -0.4686   -2.5753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1751   -1.0978   -2.5593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1929   -1.1173   -3.9988 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6236   -1.6986   -1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8542   -1.6634   -0.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6053   -1.0137   -0.3178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0891   -1.1601    0.9906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2291   -1.2116    1.8679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9367   -1.7462    3.2100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9751    0.1022    1.8302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0732   -2.2301    1.0675 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0202    1.1107    0.6741 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0329   -0.4497   -0.6007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9826    0.0388    1.0873 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9602    1.3135   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8630    1.5920    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7135    3.1247   -0.0422 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9671    3.3703   -0.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9788    2.2933   -2.3047 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7592    2.2307   -2.1217 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.1217   -1.9820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9913   -0.0703   -2.5090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3661   -1.0904   -1.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3080    1.7353   -1.2700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0672   -0.2396    0.4132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6362   -0.0045   -3.5034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5789   -2.2030   -1.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2050   -2.8343    3.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8301   -1.6334    3.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4985   -1.1789    4.0056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3756    0.8652    2.3133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1701    0.3015    0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9457   -0.0920    2.3461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6696   -3.2430    1.1752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1386   -2.1481    1.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4458    1.8913    1.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9620    0.1799    1.3032 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  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  8 24  1  0
  6  2  1  0
 18 12  1  0
 24  3  1  0
 23 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
 13 38  1  0
 16 39  1  0
 21 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 24 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-Chloro-2,2-dimethyl-N-{8-methyl-8-azabicyclo[3.2.1]octan-3-yl}-2,3-dihydro-1-benzofuran-7-carboximidate	Generator
5-Chloro-2,3-dihydro-2,2-dimethyl-N-(8-methyl-8-azabicyclo(3.2.1)oct-3-yl)-7-benzofurancarboxamide	MeSH
LY 277359 maleate	MeSH
Zatosetron maleate	MeSH

Chemical Formula

C₁₉H₂₅ClN₂O₂

Average Molecular Weight

348.87

Monoisotopic Molecular Weight

348.1604558

IUPAC Name

5-chloro-2,2-dimethyl-N-{8-methyl-8-azabicyclo[3.2.1]octan-3-yl}-2,3-dihydro-1-benzofuran-7-carboxamide

Traditional Name

zatosetron

CAS Registry Number

Not Available

SMILES

CN1C2CCC1CC(C2)NC(=O)C1=CC(Cl)=CC2=C1OC(C)(C)C2

InChI Identifier

InChI=1S/C19H25ClN2O2/c1-19(2)10-11-6-12(20)7-16(17(11)24-19)18(23)21-13-8-14-4-5-15(9-13)22(14)3/h6-7,13-15H,4-5,8-10H2,1-3H3,(H,21,23)

InChI Key

SPKBYQZELVEOLL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]Octane.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Tropane alkaloids

Sub Class

Not Available

Direct Parent

Tropane alkaloids

Alternative Parents

Substituents

Coumaran
Tropane alkaloid
Alkyl aryl ether
Aryl chloride
Aryl halide
Piperidine
Benzenoid
N-alkylpyrrolidine
Pyrrolidine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Organochloride
Organohalogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.67	ALOGPS
logP	2.78	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.84	ChemAxon
pKa (Strongest Basic)	9.18	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.57 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96 m³·mol⁻¹	ChemAxon
Polarizability	38.6 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
AllCCS	[M+H]+	183.999	32859911
AllCCS	[M+H-H2O]+	181.228	32859911
AllCCS	[M+Na]+	187.29	32859911
AllCCS	[M+NH4]+	186.557	32859911
AllCCS	[M-H]-	185.479	32859911
AllCCS	[M+Na-2H]-	185.652	32859911
AllCCS	[M+HCOO]-	185.98	32859911
DeepCCS	[M+H]+	176.543	30932474
DeepCCS	[M-H]-	174.185	30932474
DeepCCS	[M-2H]-	207.332	30932474
DeepCCS	[M+Na]+	182.762	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
ZATOSETRON	CN1C2CCC1CC(C2)NC(=O)C1=CC(Cl)=CC2=C1OC(C)(C)C2	3436.0	Standard polar	33892256
ZATOSETRON	CN1C2CCC1CC(C2)NC(=O)C1=CC(Cl)=CC2=C1OC(C)(C)C2	2830.5	Standard non polar	33892256
ZATOSETRON	CN1C2CCC1CC(C2)NC(=O)C1=CC(Cl)=CC2=C1OC(C)(C)C2	2790.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
ZATOSETRON,1TMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C)C2	2689.5	Semi standard non polar	33892256
ZATOSETRON,1TMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C)C2	2674.4	Standard non polar	33892256
ZATOSETRON,1TMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C)C2	3297.1	Standard polar	33892256
ZATOSETRON,1TBDMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C(C)(C)C)C2	2906.1	Semi standard non polar	33892256
ZATOSETRON,1TBDMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C(C)(C)C)C2	2920.2	Standard non polar	33892256
ZATOSETRON,1TBDMS,isomer #1	CN1C2CCC1CC(N(C(=O)C1=CC(Cl)=CC3=C1OC(C)(C)C3)[Si](C)(C)C(C)(C)C)C2	3390.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Zatosetron GC-MS (Non-derivatized) - 70eV, Positive	splash10-053s-9345000000-8be032abaeecc59817cf	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zatosetron GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

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

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

54761

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60763

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for Zatosetron (HMDB0259991)

MOL for HMDB0259991 (Zatosetron)

3D MOL for HMDB0259991 (Zatosetron)

3D SDF for HMDB0259991 (Zatosetron)

3D-SDF for HMDB0259991 (Zatosetron)

PDB for HMDB0259991 (Zatosetron)

3D PDB for HMDB0259991 (Zatosetron)

SMILES for HMDB0259991 (Zatosetron)

INCHI for HMDB0259991 (Zatosetron)

Structure for HMDB0259991 (Zatosetron)

3D Structure for HMDB0259991 (Zatosetron)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra