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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:11:18 UTC

Update Date

2022-03-07 02:53:43 UTC

HMDB ID

HMDB0033454

Secondary Accession Numbers

HMDB33454

Metabolite Identification

Common Name

3alpha-Tigloyloxytropane N-oxide

Description

3alpha-Tigloyloxytropane N-oxide 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. 3alpha-Tigloyloxytropane N-oxide is a moderately basic compound (based on its pKa). Outside of the human body, 3alpha-tigloyloxytropane N-oxide has been detected, but not quantified in, fruits. This could make 3alpha-tigloyloxytropane N-oxide a potential biomarker for the consumption of these foods.

Structure

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

HMDB0033454
     RDKit          3D
3alpha-Tigloyloxytropane N-oxide
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.8731    1.5445   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    0.9736   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740   -0.2445   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.0944    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -0.7371    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986   -1.8969    0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135    0.0448   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874   -0.4243    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059    0.4116    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132    0.3173    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -1.1559    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466   -1.6401   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924   -0.4648   -0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.5020   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.6516   -0.1327 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6386    1.9181   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169    0.6668   -0.0318 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.5420    1.4269   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3537    1.1188   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    2.6444   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    1.5793   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3616   -0.5149    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -1.9488    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -1.5190   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145   -1.4764    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    1.4576    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    0.0732    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.9243    1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7102   -1.2601    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186   -1.7277    1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2575   -1.6986   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -2.5709   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4599   -1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2798   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.4859   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    2.0238   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919    2.7058    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129    2.0599   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  CHG  2  15   1  17  -1
M  END


  Mrv0541 05061307082D          

 17 18  0  0  0  0            999 V2000
    2.5365   -4.9319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3629   -3.5037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3203   -0.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1247   -4.2170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9893   -0.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5379   -3.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1261   -2.7880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3011   -2.7872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8111    0.6467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5393   -2.0740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  6  5  1  0  0  0  0
  9  2  1  0  0  0  0
  9  4  2  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  2  0  0  0  0
 16 14  2  0  0  0  0
 17 12  1  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033454

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/C)C(=O)OC1CC2CCC(C1)N2(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H21NO3/c1-4-9(2)13(15)17-12-7-10-5-6-11(8-12)14(10,3)16/h4,10-12H,5-8H2,1-3H3/b9-4+

> <INCHI_KEY>
VNARLHBYSZUQEN-RUDMXATFSA-N

> <FORMULA>
C13H21NO3

> <MOLECULAR_WEIGHT>
239.3107

> <EXACT_MASS>
239.152143543

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.17598335666786

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-methyl-8-oxo-8λ⁵-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
-0.19

> <JCHEM_LOGP>
1.122122716333333

> <ALOGPS_LOGS>
-2.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.651480662613775

> <JCHEM_PKA_STRONGEST_BASIC>
2.539722797758849

> <JCHEM_POLAR_SURFACE_AREA>
53.18000000000001

> <JCHEM_REFRACTIVITY>
66.4685

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-methyl-8-oxo-8λ⁵-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033454
     RDKit          3D
3alpha-Tigloyloxytropane N-oxide
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.8731    1.5445   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    0.9736   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740   -0.2445   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.0944    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -0.7371    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986   -1.8969    0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135    0.0448   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874   -0.4243    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059    0.4116    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132    0.3173    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -1.1559    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466   -1.6401   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924   -0.4648   -0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.5020   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.6516   -0.1327 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6386    1.9181   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169    0.6668   -0.0318 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.5420    1.4269   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3537    1.1188   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    2.6444   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    1.5793   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3616   -0.5149    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -1.9488    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -1.5190   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145   -1.4764    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    1.4576    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    0.0732    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.9243    1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7102   -1.2601    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186   -1.7277    1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2575   -1.6986   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -2.5709   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4599   -1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2798   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.4859   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    2.0238   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919    2.7058    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129    2.0599   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  CHG  2  15   1  17  -1
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.735  -9.206   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.277  -6.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.598  -0.052   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.966  -7.872   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.713  -1.011   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.008  -1.737   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.737  -6.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.969  -5.204   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       0.933  -0.219   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       2.429  -5.203   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.514   1.207   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.740  -3.871   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3   14                                                            
CONECT    4    1    9                                                       
CONECT    5    6   10                                                       
CONECT    6    5   11                                                       
CONECT    7   10   12                                                       
CONECT    8   11   12                                                       
CONECT    9    2    4   13                                                  
CONECT   10    5    7   14                                                  
CONECT   11    6    8   14                                                  
CONECT   12    7    8   17                                                  
CONECT   13    9   15   17                                                  
CONECT   14    3   10   11   16                                             
CONECT   15   13                                                            
CONECT   16   14                                                            
CONECT   17   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0033454
HETATM    1  C1  UNL     1       4.873   1.544  -0.906  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.531   0.974  -0.643  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.374  -0.244  -0.170  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.541  -1.094   0.119  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.030  -0.737   0.063  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.799  -1.897   0.517  1.00  0.00           O  
HETATM    7  O2  UNL     1       0.914   0.045  -0.201  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.387  -0.424   0.022  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.006   0.412   1.107  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.513   0.317   1.138  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.857  -1.156   1.290  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.147  -1.640  -0.106  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.692  -0.465  -0.960  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.215  -0.502  -1.225  1.00  0.00           C  
HETATM   15  N1  UNL     1      -3.074   0.652  -0.133  1.00  0.00           N1+
HETATM   16  C13 UNL     1      -2.639   1.918  -0.650  1.00  0.00           C  
HETATM   17  O3  UNL     1      -4.417   0.667  -0.032  1.00  0.00           O1-
HETATM   18  H1  UNL     1       5.542   1.427  -0.010  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.354   1.119  -1.790  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.790   2.644  -1.058  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.637   1.579  -0.847  1.00  0.00           H  
HETATM   22  H5  UNL     1       5.362  -0.515   0.591  1.00  0.00           H  
HETATM   23  H6  UNL     1       4.230  -1.949   0.751  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.910  -1.519  -0.849  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.315  -1.476   0.424  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.676   1.458   0.968  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.573   0.073   2.069  1.00  0.00           H  
HETATM   28  H11 UNL     1      -2.880   0.924   1.967  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.710  -1.260   1.973  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.019  -1.728   1.720  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.258  -1.699  -0.231  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.644  -2.571  -0.365  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.207  -0.460  -1.941  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.987   0.280  -1.969  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.000  -1.486  -1.724  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.564   2.024  -0.779  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.992   2.706   0.042  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.113   2.060  -1.646  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   21
CONECT    3    4    5
CONECT    4   22   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   14   25
CONECT    9   10   26   27
CONECT   10   11   15   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   15   33
CONECT   14   34   35
CONECT   15   16   17
CONECT   16   36   37   38
END

HMDB0033454
     RDKit          3D
3alpha-Tigloyloxytropane N-oxide
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.8731    1.5445   -0.9058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5309    0.9736   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3740   -0.2445   -0.1696 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5407   -1.0944    0.1192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301   -0.7371    0.0634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7986   -1.8969    0.5166 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9135    0.0448   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3874   -0.4243    0.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0059    0.4116    1.1072 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5132    0.3173    1.1377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -1.1559    1.2899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1466   -1.6401   -0.1057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6924   -0.4648   -0.9604 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2150   -0.5020   -1.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0741    0.6516   -0.1327 N   0  0  0  0  0  4  0  0  0  0  0  0
   -2.6386    1.9181   -0.6503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4169    0.6668   -0.0318 O   0  0  0  0  0  1  0  0  0  0  0  0
    5.5420    1.4269   -0.0098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3537    1.1188   -1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7901    2.6444   -1.0577 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371    1.5793   -0.8466 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3616   -0.5149    0.5908 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2297   -1.9488    0.7508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9096   -1.5190   -0.8490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3145   -1.4764    0.4236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6763    1.4576    0.9679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5733    0.0732    2.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8797    0.9243    1.9666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7102   -1.2601    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0186   -1.7277    1.7201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2575   -1.6986   -0.2308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6438   -2.5709   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2071   -0.4599   -1.9412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9872    0.2798   -1.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0004   -1.4859   -1.7241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5641    2.0238   -0.7793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9919    2.7058    0.0425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1129    2.0599   -1.6458 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 14  8  1  0
 15 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  CHG  2  15   1  17  -1
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3a-Tigloyloxytropane N-oxide	Generator
3Α-tigloyloxytropane N-oxide	Generator
8-Methyl-8-oxo-8λ⁵-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₁₃H₂₁NO₃

Average Molecular Weight

239.3107

Monoisotopic Molecular Weight

239.152143543

IUPAC Name

8-methyl-8-oxo-8λ⁵-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

Traditional Name

8-methyl-8-oxo-8λ⁵-azabicyclo[3.2.1]octan-3-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)OC1CC2CCC(C1)N2(C)=O

InChI Identifier

InChI=1S/C13H21NO3/c1-4-9(2)13(15)17-12-7-10-5-6-11(8-12)14(10,3)16/h4,10-12H,5-8H2,1-3H3/b9-4+

InChI Key

VNARLHBYSZUQEN-RUDMXATFSA-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

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033454)
Cytoplasm (HMDB: HMDB0033454)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033454)

Source

Exogenous

Food

Food (HMDB: HMDB0033454)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0033454)

Not Available

Nutrient (HMDB: HMDB0033454)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	185 - 186 °C	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	0.39 g/L	ALOGPS
logP	-0.19	ALOGPS
logP	1.12	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	19.65	ChemAxon
pKa (Strongest Basic)	2.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.18 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.47 m³·mol⁻¹	ChemAxon
Polarizability	26.18 Å³	ChemAxon
Number of Rings	2	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]+	158.791	31661259
DarkChem	[M-H]-	154.962	31661259
DeepCCS	[M+H]+	157.143	30932474
DeepCCS	[M-H]-	154.785	30932474
DeepCCS	[M-2H]-	188.044	30932474
DeepCCS	[M+Na]+	163.241	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	159.3	32859911
AllCCS	[M+Na-2H]-	159.8	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3alpha-Tigloyloxytropane N-oxide	C\C=C(/C)C(=O)OC1CC2CCC(C1)N2(C)=O	2389.1	Standard polar	33892256
3alpha-Tigloyloxytropane N-oxide	C\C=C(/C)C(=O)OC1CC2CCC(C1)N2(C)=O	1602.7	Standard non polar	33892256
3alpha-Tigloyloxytropane N-oxide	C\C=C(/C)C(=O)OC1CC2CCC(C1)N2(C)=O	1736.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Tigloyloxytropane N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-06sj-9410000000-4ce157608e07c5ec0aa5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 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 - 3alpha-Tigloyloxytropane N-oxide 10V, Positive-QTOF	splash10-0006-3490000000-716a53bde2f18f3ebb33	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 20V, Positive-QTOF	splash10-0006-9820000000-b2f0d48cce4877180532	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 40V, Positive-QTOF	splash10-0pb9-9300000000-f4cab4fda32d08985259	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 10V, Negative-QTOF	splash10-000i-1090000000-2eee03523c235995f33e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 20V, Negative-QTOF	splash10-000i-7090000000-0d0090d61c58194b5214	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 40V, Negative-QTOF	splash10-0a4i-9000000000-03df8ab066b82e1dfe3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 10V, Positive-QTOF	splash10-0006-0190000000-4035e9ba14c38ba3ce5a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 20V, Positive-QTOF	splash10-00dl-0910000000-1c8928cef8a514d4af19	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 40V, Positive-QTOF	splash10-0ab9-9800000000-953223adab4c2a218b02	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 10V, Negative-QTOF	splash10-000b-9060000000-166cc6d8adab67b82c49	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 20V, Negative-QTOF	splash10-0002-9010000000-23c933ce673c924669ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3alpha-Tigloyloxytropane N-oxide 40V, Negative-QTOF	splash10-0pba-9000000000-9d3e727c5d6b9ff69c1f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB011493

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

131751426

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3alpha-Tigloyloxytropane N-oxide (HMDB0033454)

MOL for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

3D MOL for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

3D SDF for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

3D-SDF for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

PDB for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

3D PDB for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

SMILES for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

INCHI for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

Structure for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

3D Structure for HMDB0033454 (3alpha-Tigloyloxytropane N-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra