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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:54:47 UTC

Update Date

2022-03-07 02:55:50 UTC

HMDB ID

HMDB0038588

Secondary Accession Numbers

HMDB38588

Metabolite Identification

Common Name

Dioscoretine

Description

Dioscoretine belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain. Based on a literature review a small amount of articles have been published on Dioscoretine.

Structure

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

HMDB0038588
     RDKit          3D
Dioscoretine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.6740    0.4336    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1901   -0.0839    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -0.0788   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609   -0.9306   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382   -1.5790    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -1.0310   -1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.6384   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2117    0.6335    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    1.2309    1.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.4584   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    0.8600   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    0.5178    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807   -0.5983    1.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -0.7391    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -1.2007   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -0.3239   -0.7902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -0.9266   -0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441   -0.2391    2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    0.5193    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.4567    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325   -1.1713    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.4643   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634    0.9689   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2633   -0.2741   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    0.1546   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872    1.6933   -0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.2089    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    2.5243   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    1.3111   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4439    1.5799   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701    1.4030    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6578    0.1467    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -1.5353    2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -0.3106    2.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164   -1.5148    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667   -1.2451   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.2462   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842   -0.4453   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -2.0103   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329   -0.7908    0.1717 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  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 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
 16 17  1  0
 14  8  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

  Mrv0541 05061310322D          

 17 18  0  0  0  0            999 V2000
   -1.2116    0.3682    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
   -1.4976   -1.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1422   -0.5795    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
   -0.9505   -0.4144    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
   -2.3059   -0.8667    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
   -2.5671   -0.0842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8531   -1.4842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6840   -1.5514    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  1  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
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038588

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC(O)=O)CC1(O)CC2CCC1CN2C

> <INCHI_IDENTIFIER>
InChI=1S/C13H23NO3/c1-9(5-12(15)16)6-13(17)7-11-4-3-10(13)8-14(11)2/h9-11,17H,3-8H2,1-2H3,(H,15,16)

> <INCHI_KEY>
YWVYEZNFPRWGMM-UHFFFAOYSA-N

> <FORMULA>
C13H23NO3

> <MOLECULAR_WEIGHT>
241.3266

> <EXACT_MASS>
241.167793607

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.467170673364386

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{5-hydroxy-2-methyl-2-azabicyclo[2.2.2]octan-5-yl}-3-methylbutanoic acid

> <ALOGPS_LOGP>
0.47

> <JCHEM_LOGP>
-2.050772308074806

> <ALOGPS_LOGS>
-1.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.454748913652402

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.482864001764739

> <JCHEM_PKA_STRONGEST_BASIC>
8.949438803015436

> <JCHEM_POLAR_SURFACE_AREA>
60.77000000000001

> <JCHEM_REFRACTIVITY>
65.2466

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-hydroxy-2-methyl-2-azabicyclo[2.2.2]octan-5-yl}-3-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038588
     RDKit          3D
Dioscoretine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.6740    0.4336    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1901   -0.0839    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -0.0788   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609   -0.9306   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382   -1.5790    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -1.0310   -1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.6384   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2117    0.6335    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    1.2309    1.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.4584   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    0.8600   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    0.5178    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807   -0.5983    1.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -0.7391    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -1.2007   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -0.3239   -0.7902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -0.9266   -0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441   -0.2391    2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    0.5193    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.4567    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325   -1.1713    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.4643   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634    0.9689   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2633   -0.2741   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    0.1546   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872    1.6933   -0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.2089    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    2.5243   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    1.3111   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4439    1.5799   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701    1.4030    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6578    0.1467    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -1.5353    2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -0.3106    2.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164   -1.5148    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667   -1.2451   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.2462   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842   -0.4453   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -2.0103   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329   -0.7908    0.1717 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  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 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
 16 17  1  0
 14  8  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  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      -2.262   0.687   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      -2.796  -1.926   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.265  -1.082   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      -1.774  -0.774   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      -4.304  -1.618   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      -4.792  -0.157   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -5.326  -2.771   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.277  -2.896   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   17                                             
CONECT   14    2    8   11                                                  
CONECT   15   12                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0038588
HETATM    1  C1  UNL     1       2.674   0.434   1.372  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.190  -0.084   0.069  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.330  -0.079  -0.923  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.461  -0.931  -0.482  1.00  0.00           C  
HETATM    5  O1  UNL     1       4.438  -1.579   0.593  1.00  0.00           O  
HETATM    6  O2  UNL     1       5.596  -1.031  -1.268  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.015   0.638  -0.517  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.212   0.633   0.316  1.00  0.00           C  
HETATM    9  O3  UNL     1      -0.008   1.231   1.558  1.00  0.00           O  
HETATM   10  C7  UNL     1      -1.269   1.458  -0.394  1.00  0.00           C  
HETATM   11  C8  UNL     1      -2.626   0.860  -0.012  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.651   0.518   1.471  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.681  -0.598   1.798  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.776  -0.739   0.567  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.677  -1.201  -0.569  1.00  0.00           C  
HETATM   16  N1  UNL     1      -2.779  -0.324  -0.790  1.00  0.00           N  
HETATM   17  C13 UNL     1      -4.062  -0.927  -0.754  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.444  -0.239   2.235  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.778   0.519   1.343  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.311   1.457   1.600  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.932  -1.171   0.217  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.005  -0.464  -1.915  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.663   0.969  -1.104  1.00  0.00           H  
HETATM   24  H7  UNL     1       6.263  -0.274  -1.322  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.779   0.155  -1.490  1.00  0.00           H  
HETATM   26  H9  UNL     1       1.287   1.693  -0.729  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.020   2.209   1.395  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.215   2.524  -0.157  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.182   1.311  -1.490  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.444   1.580  -0.183  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.470   1.403   2.092  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.658   0.147   1.700  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.162  -1.535   2.072  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.985  -0.311   2.630  1.00  0.00           H  
HETATM   35  H18 UNL     1      -0.016  -1.515   0.717  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.067  -1.245  -1.481  1.00  0.00           H  
HETATM   37  H20 UNL     1      -1.993  -2.246  -0.283  1.00  0.00           H  
HETATM   38  H21 UNL     1      -4.684  -0.445  -1.565  1.00  0.00           H  
HETATM   39  H22 UNL     1      -3.939  -2.010  -1.024  1.00  0.00           H  
HETATM   40  H23 UNL     1      -4.633  -0.791   0.172  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    7   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6   24
CONECT    7    8   25   26
CONECT    8    9   10   14
CONECT    9   27
CONECT   10   11   28   29
CONECT   11   12   16   30
CONECT   12   13   31   32
CONECT   13   14   33   34
CONECT   14   15   35
CONECT   15   16   36   37
CONECT   16   17
CONECT   17   38   39   40
END

HMDB0038588
     RDKit          3D
Dioscoretine
 40 41  0  0  0  0  0  0  0  0999 V2000
    2.6740    0.4336    1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1901   -0.0839    0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -0.0788   -0.9228 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4609   -0.9306   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4382   -1.5790    0.5927 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5965   -1.0310   -1.2675 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0153    0.6384   -0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2117    0.6335    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0076    1.2309    1.5575 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    1.4584   -0.3941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6256    0.8600   -0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6512    0.5178    1.4708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6807   -0.5983    1.7979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7763   -0.7391    0.5670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6768   -1.2007   -0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -0.3239   -0.7902 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0625   -0.9266   -0.7535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4441   -0.2391    2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7778    0.5193    1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3108    1.4567    1.6003 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9325   -1.1713    0.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0049   -0.4643   -1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6634    0.9689   -1.1040 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2633   -0.2741   -1.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7794    0.1546   -1.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2872    1.6933   -0.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0198    2.2089    1.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2149    2.5243   -0.1565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1817    1.3111   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4439    1.5799   -0.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701    1.4030    2.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6578    0.1467    1.7004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1618   -1.5353    2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9850   -0.3106    2.6301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0164   -1.5148    0.7171 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667   -1.2451   -1.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9931   -2.2462   -0.2825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6842   -0.4453   -1.5655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9394   -2.0103   -1.0244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6329   -0.7908    0.1717 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  2  0
  4  6  1  0
  2  7  1  0
  7  8  1  0
  8  9  1  0
  8 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
 16 17  1  0
 14  8  1  0
 16 11  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Dioscoretin	HMDB
4-{5-hydroxy-2-methyl-2-azabicyclo[2.2.2]octan-5-yl}-3-methylbutanoate	Generator
Dioscoretine	MeSH

Chemical Formula

C₁₃H₂₃NO₃

Average Molecular Weight

241.3266

Monoisotopic Molecular Weight

241.167793607

IUPAC Name

4-{5-hydroxy-2-methyl-2-azabicyclo[2.2.2]octan-5-yl}-3-methylbutanoic acid

Traditional Name

4-{5-hydroxy-2-methyl-2-azabicyclo[2.2.2]octan-5-yl}-3-methylbutanoic acid

CAS Registry Number

128637-87-6

SMILES

CC(CC(O)=O)CC1(O)CC2CCC1CN2C

InChI Identifier

InChI=1S/C13H23NO3/c1-9(5-12(15)16)6-13(17)7-11-4-3-10(13)8-14(11)2/h9-11,17H,3-8H2,1-2H3,(H,15,16)

InChI Key

YWVYEZNFPRWGMM-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heterocyclic fatty acids. These are fatty acids containing a heterocyclic attached to the acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Heterocyclic fatty acids

Alternative Parents

Substituents

Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Methyl-branched fatty acid
Piperidine
Cyclic alcohol
Tertiary alcohol
Amino acid or derivatives
Amino acid
Tertiary aliphatic amine
Tertiary amine
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Alcohol
Carbonyl group
Amine
Organonitrogen compound
Organooxygen compound
Organic nitrogen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Adiposome (HMDB: HMDB0038588)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038588)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038588)

Source

Endogenous

Endogenous (HMDB: HMDB0038588)

Plant

Plant (HMDB: HMDB0038588)

Animal

Animal (HMDB: HMDB0038588)

Exogenous

Food

Food (HMDB: HMDB0038588)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0038588)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038588)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038588)

Lipid metabolism pathway (HMDB: HMDB0038588)

Cellular process

Cell signaling (HMDB: HMDB0038588)

Biochemical process

Lipid transport (HMDB: HMDB0038588)

Role

Biological role

Energy source (HMDB: HMDB0038588)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038588)

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	8551 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	13.9 g/L	ALOGPS
logP	0.47	ALOGPS
logP	-2.1	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.48	ChemAxon
pKa (Strongest Basic)	8.95	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.77 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	65.25 m³·mol⁻¹	ChemAxon
Polarizability	26.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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]+	158.243	31661259
DarkChem	[M-H]-	152.218	31661259
DeepCCS	[M+H]+	154.356	30932474
DeepCCS	[M-H]-	151.998	30932474
DeepCCS	[M-2H]-	185.99	30932474
DeepCCS	[M+Na]+	160.943	30932474
AllCCS	[M+H]+	158.0	32859911
AllCCS	[M+H-H2O]+	154.5	32859911
AllCCS	[M+NH4]+	161.3	32859911
AllCCS	[M+Na]+	162.3	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	162.5	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dioscoretine	CC(CC(O)=O)CC1(O)CC2CCC1CN2C	2683.9	Standard polar	33892256
Dioscoretine	CC(CC(O)=O)CC1(O)CC2CCC1CN2C	1817.9	Standard non polar	33892256
Dioscoretine	CC(CC(O)=O)CC1(O)CC2CCC1CN2C	1917.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dioscoretine,1TMS,isomer #1	CC(CC(=O)O[Si](C)(C)C)CC1(O)CC2CCC1CN2C	1971.9	Semi standard non polar	33892256
Dioscoretine,1TMS,isomer #2	CC(CC(=O)O)CC1(O[Si](C)(C)C)CC2CCC1CN2C	1976.1	Semi standard non polar	33892256
Dioscoretine,2TMS,isomer #1	CC(CC(=O)O[Si](C)(C)C)CC1(O[Si](C)(C)C)CC2CCC1CN2C	1962.3	Semi standard non polar	33892256
Dioscoretine,1TBDMS,isomer #1	CC(CC(=O)O[Si](C)(C)C(C)(C)C)CC1(O)CC2CCC1CN2C	2230.3	Semi standard non polar	33892256
Dioscoretine,1TBDMS,isomer #2	CC(CC(=O)O)CC1(O[Si](C)(C)C(C)(C)C)CC2CCC1CN2C	2199.9	Semi standard non polar	33892256
Dioscoretine,2TBDMS,isomer #1	CC(CC(=O)O[Si](C)(C)C(C)(C)C)CC1(O[Si](C)(C)C(C)(C)C)CC2CCC1CN2C	2407.0	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 - Dioscoretine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-5910000000-bf92cb60256dafb5d3af	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioscoretine GC-MS (2 TMS) - 70eV, Positive	splash10-03k9-6093000000-013239f6e5a653159a14	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioscoretine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dioscoretine 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 - Dioscoretine 10V, Positive-QTOF	splash10-00dl-0390000000-6cc38385805d3282012b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 20V, Positive-QTOF	splash10-070w-1920000000-cd46305c70ad67ca654e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 40V, Positive-QTOF	splash10-01ox-5900000000-2222e3bd911daaf995d4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 10V, Negative-QTOF	splash10-0006-0490000000-ed147a32337b0bbcf915	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 20V, Negative-QTOF	splash10-0097-2980000000-7f95cca28b8215427464	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 40V, Negative-QTOF	splash10-0a4l-7910000000-f1a624ad425d9e151f16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 10V, Positive-QTOF	splash10-00dl-0090000000-18b7800fcd49eb44bfba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 20V, Positive-QTOF	splash10-00di-0980000000-170a5f28c4c49535678e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 40V, Positive-QTOF	splash10-024i-0910000000-ce39ca665f293e782f1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 10V, Negative-QTOF	splash10-0006-0090000000-3ecb1db5775da190b7b1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 20V, Negative-QTOF	splash10-0006-0090000000-c91429f9ba4cfdfd7681	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dioscoretine 40V, Negative-QTOF	splash10-00dl-2980000000-777f1cecfad8434581b0	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB017978

KNApSAcK ID

Not Available

Chemspider ID

8235809

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10060255

PDB ID

Not Available

ChEBI ID

173742

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1869641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Dioscoretine (HMDB0038588)

MOL for HMDB0038588 (Dioscoretine)

3D MOL for HMDB0038588 (Dioscoretine)

3D SDF for HMDB0038588 (Dioscoretine)

3D-SDF for HMDB0038588 (Dioscoretine)

PDB for HMDB0038588 (Dioscoretine)

3D PDB for HMDB0038588 (Dioscoretine)

SMILES for HMDB0038588 (Dioscoretine)

INCHI for HMDB0038588 (Dioscoretine)

Structure for HMDB0038588 (Dioscoretine)

3D Structure for HMDB0038588 (Dioscoretine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra