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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:01 UTC

Update Date

2022-03-07 02:52:30 UTC

HMDB ID

HMDB0030305

Secondary Accession Numbers

HMDB30305

Metabolite Identification

Common Name

Dioscorine

Description

Dioscorine belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom. Based on a literature review very few articles have been published on Dioscorine.

Structure

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

HMDB0030305
     RDKit          3D
Dioscorine
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7658    1.0490   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    0.1097   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047   -0.3970    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2187   -1.2976    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -1.7640    2.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.6138    1.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945   -0.5965    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -0.2367   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769    0.6317    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    0.9271    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276   -0.2065    1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.5016    0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -1.2231   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.2942   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    0.9804   -0.7173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210    1.3413   -0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.5596   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8539    1.9926   -0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    1.2651   -1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.1111    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260    0.6200   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051   -1.1263   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.5463    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    0.5346    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6124    1.8894    1.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.1152    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.0553    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281   -2.2569    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881   -1.9068    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -2.1525   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -0.1081   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4653   -0.7651   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    1.8483   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7541    0.4080   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658    2.0252   -0.0645 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 15 10  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END


  Mrv0541 05061305092D          

 16 18  0  0  0  0            999 V2000
   -1.9683   -2.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3244   -2.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9605   -0.1141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3896   -0.6939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5475   -1.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2262   -2.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6614   -1.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3018   -1.5142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9228   -1.0102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0655   -1.7586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7231   -0.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -1.3621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8140   -2.1055    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8110    0.6126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -0.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  2  0  0  0  0
  9  6  1  0  0  0  0
 10  3  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 10  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
 16 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030305

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CC2CCC1CC21CC(C)=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C13H19NO2/c1-9-5-12(15)16-13(6-9)7-11-4-3-10(13)8-14(11)2/h5,10-11H,3-4,6-8H2,1-2H3

> <INCHI_KEY>
YBQKKTNDAXVYGX-UHFFFAOYSA-N

> <FORMULA>
C13H19NO2

> <MOLECULAR_WEIGHT>
221.2955

> <EXACT_MASS>
221.141578857

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.53597898760312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4',5-dimethyl-3',6'-dihydro-5-azaspiro[bicyclo[2.2.2]octane-2,2'-pyran]-6'-one

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
1.5293393173333323

> <ALOGPS_LOGS>
-0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.119061843986326

> <JCHEM_PKA_STRONGEST_BASIC>
9.306573151653453

> <JCHEM_POLAR_SURFACE_AREA>
29.540000000000003

> <JCHEM_REFRACTIVITY>
62.581100000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.33e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4',5-dimethyl-3'H-5-azaspiro[bicyclo[2.2.2]octane-2,2'-pyran]-6'-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030305
     RDKit          3D
Dioscorine
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7658    1.0490   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    0.1097   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047   -0.3970    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2187   -1.2976    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -1.7640    2.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.6138    1.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945   -0.5965    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -0.2367   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769    0.6317    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    0.9271    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276   -0.2065    1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.5016    0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -1.2231   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.2942   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    0.9804   -0.7173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210    1.3413   -0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.5596   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8539    1.9926   -0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    1.2651   -1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.1111    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260    0.6200   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051   -1.1263   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.5463    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    0.5346    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6124    1.8894    1.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.1152    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.0553    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281   -2.2569    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881   -1.9068    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -2.1525   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -0.1081   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4653   -0.7651   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    1.8483   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7541    0.4080   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658    2.0252   -0.0645 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 15 10  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
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      -3.674  -3.734   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.339  -5.140   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.793  -0.213   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.250  -1.344   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.594  -1.295   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.022  -3.450   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.422  -3.953   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.101  -2.506   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.430  -2.827   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.723  -1.886   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.989  -3.283   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.350  -0.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.222  -2.543   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.386  -3.930   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -1.514   1.144   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.058  -1.011   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   14                                                            
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    9   12                                                       
CONECT    6    9   13                                                       
CONECT    7   11   13                                                       
CONECT    8   10   14                                                       
CONECT    9    1    5    6                                                  
CONECT   10    3    8   13                                                  
CONECT   11    4    7   14                                                  
CONECT   12    5   15   16                                                  
CONECT   13    6    7   10   16                                             
CONECT   14    2    8   11                                                  
CONECT   15   12                                                            
CONECT   16   12   13                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0030305
HETATM    1  C1  UNL     1      -3.766   1.049  -0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.787   0.110  -0.225  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.105  -0.397   0.941  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.219  -1.298   1.643  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.560  -1.764   2.759  1.00  0.00           O  
HETATM    6  O2  UNL     1      -1.003  -1.614   1.039  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.495  -0.596   0.144  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.512  -0.237  -0.874  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.077   0.632   0.899  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.402   0.927   0.689  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.228  -0.206   1.290  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.671  -1.502   0.758  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.753  -1.223  -0.438  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.488  -0.294  -1.357  1.00  0.00           C  
HETATM   15  N1  UNL     1       1.725   0.980  -0.717  1.00  0.00           N  
HETATM   16  C13 UNL     1       3.121   1.341  -0.844  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.762   0.560  -0.881  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.854   1.993  -0.337  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.389   1.265  -1.901  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.090  -0.111   1.383  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.126   0.620  -1.467  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.705  -1.126  -1.543  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.614   1.546   0.524  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.241   0.535   1.981  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.612   1.889   1.154  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.092  -0.115   2.406  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.280  -0.055   1.040  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.428  -2.257   0.533  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.988  -1.907   1.553  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.551  -2.152  -0.970  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.978  -0.108  -2.307  1.00  0.00           H  
HETATM   32  H16 UNL     1       2.465  -0.765  -1.588  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.301   1.848  -1.834  1.00  0.00           H  
HETATM   34  H18 UNL     1       3.754   0.408  -0.905  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.466   2.025  -0.065  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    8
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8    9   13
CONECT    8   21   22
CONECT    9   10   23   24
CONECT   10   11   15   25
CONECT   11   12   26   27
CONECT   12   13   28   29
CONECT   13   14   30
CONECT   14   15   31   32
CONECT   15   16
CONECT   16   33   34   35
END

HMDB0030305
     RDKit          3D
Dioscorine
 35 37  0  0  0  0  0  0  0  0999 V2000
   -3.7658    1.0490   -0.9015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7875    0.1097   -0.2246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1047   -0.3970    0.9406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2187   -1.2976    1.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -1.7640    2.7588 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0033   -1.6138    1.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4945   -0.5965    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5122   -0.2367   -0.8743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0769    0.6317    0.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    0.9271    0.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2276   -0.2065    1.2905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6709   -1.5016    0.7580 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7531   -1.2231   -0.4376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4883   -0.2942   -1.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7255    0.9804   -0.7173 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1210    1.3413   -0.8441 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7616    0.5596   -0.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8539    1.9926   -0.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3888    1.2651   -1.9013 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.1111    1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1260    0.6200   -1.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7051   -1.1263   -1.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.5463    0.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2410    0.5346    1.9809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6124    1.8894    1.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0922   -0.1152    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -0.0553    1.0398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4281   -2.2569    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9881   -1.9068    1.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5507   -2.1525   -0.9702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9783   -0.1081   -2.3066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4653   -0.7651   -1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3008    1.8483   -1.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7541    0.4080   -0.9054 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4658    2.0252   -0.0645 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
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 15 10  1  0
 13  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
  9 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2,4'-Dimethylspiro[2-azabicyclo[2.2.2]octane-5,2'-[2H]pyran]-6'(3'H)-one, 9ci	HMDB

Chemical Formula

C₁₃H₁₉NO₂

Average Molecular Weight

221.2955

Monoisotopic Molecular Weight

221.141578857

IUPAC Name

4',5-dimethyl-3',6'-dihydro-5-azaspiro[bicyclo[2.2.2]octane-2,2'-pyran]-6'-one

Traditional Name

4',5-dimethyl-3'H-5-azaspiro[bicyclo[2.2.2]octane-2,2'-pyran]-6'-one

CAS Registry Number

3329-91-7

SMILES

CN1CC2CCC1CC21CC(C)=CC(=O)O1

InChI Identifier

InChI=1S/C13H19NO2/c1-9-5-12(15)16-13(6-9)7-11-4-3-10(13)8-14(11)2/h5,10-11H,3-4,6-8H2,1-2H3

InChI Key

YBQKKTNDAXVYGX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaspirodecane derivatives. These are organic compounds containing a spirodecane moiety with at least one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaspirodecane derivatives

Sub Class

Not Available

Direct Parent

Azaspirodecane derivatives

Alternative Parents

Substituents

Azaspirodecane
Dihydropyranone
Piperidine
Pyran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Amino acid or derivatives
Carboxylic acid ester
Lactone
Tertiary amine
Tertiary aliphatic amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Azacycle
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Amine
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030305)
Cytoplasm (HMDB: HMDB0030305)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030305)

Source

Endogenous

Endogenous (HMDB: HMDB0030305)

Plant

Plant (HMDB: HMDB0030305)

Exogenous

Food

Food (HMDB: HMDB0030305)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	43.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	24070 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	23.3 g/L	ALOGPS
logP	1.74	ALOGPS
logP	1.53	ChemAxon
logS	-0.98	ALOGPS
pKa (Strongest Acidic)	17.12	ChemAxon
pKa (Strongest Basic)	9.31	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.54 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.58 m³·mol⁻¹	ChemAxon
Polarizability	24.54 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.118	31661259
DarkChem	[M-H]-	148.88	31661259
DeepCCS	[M-2H]-	180.936	30932474
DeepCCS	[M+Na]+	156.508	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.2	32859911
AllCCS	[M+NH4]+	154.9	32859911
AllCCS	[M+Na]+	156.0	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	158.0	32859911
AllCCS	[M+HCOO]-	158.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dioscorine	CN1CC2CCC1CC21CC(C)=CC(=O)O1	2708.7	Standard polar	33892256
Dioscorine	CN1CC2CCC1CC21CC(C)=CC(=O)O1	1799.4	Standard non polar	33892256
Dioscorine	CN1CC2CCC1CC21CC(C)=CC(=O)O1	1971.0	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 - Dioscorine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00nv-9210000000-7df750cbbc6e26f60e45	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioscorine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioscorine 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 - Dioscorine 10V, Positive-QTOF	splash10-0229-0970000000-baeab4d594ec7b186eeb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 20V, Positive-QTOF	splash10-00di-1910000000-f289e96dcb992915c859	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 40V, Positive-QTOF	splash10-00ei-1900000000-c64b57b33f140e9d5970	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 10V, Negative-QTOF	splash10-00fr-0690000000-bd76f99e794f4980ad6a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 20V, Negative-QTOF	splash10-00fr-1890000000-fa14d7880a1ca94a5b94	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 40V, Negative-QTOF	splash10-0kjc-4900000000-0c3bfaaaaa54d4817e11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 10V, Positive-QTOF	splash10-00di-0090000000-34a926941780a1f22aa2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 20V, Positive-QTOF	splash10-00di-0290000000-8c37f96cb5ea9d59b1b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 40V, Positive-QTOF	splash10-00el-3910000000-68d3d82f9ee9fb546284	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 10V, Negative-QTOF	splash10-00di-0090000000-25fca81a3cc6d105f9b7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 20V, Negative-QTOF	splash10-00di-0090000000-3515e3c6437506aee905	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscorine 40V, Negative-QTOF	splash10-0udi-0970000000-bd18a2eb2040a3af1b94	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dioscorine

METLIN ID

Not Available

PubChem Compound

267893

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1818861

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 Dioscorine (HMDB0030305)

MOL for HMDB0030305 (Dioscorine)

3D MOL for HMDB0030305 (Dioscorine)

3D SDF for HMDB0030305 (Dioscorine)

3D-SDF for HMDB0030305 (Dioscorine)

PDB for HMDB0030305 (Dioscorine)

3D PDB for HMDB0030305 (Dioscorine)

SMILES for HMDB0030305 (Dioscorine)

INCHI for HMDB0030305 (Dioscorine)

Structure for HMDB0030305 (Dioscorine)

3D Structure for HMDB0030305 (Dioscorine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra