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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:25:56 UTC

Update Date

2022-03-07 02:53:49 UTC

HMDB ID

HMDB0033678

Secondary Accession Numbers

HMDB33678

Metabolite Identification

Common Name

gamma-Chaconine

Description

gamma-Chaconine, also known as γ-chaconine, belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative. Based on a literature review a significant number of articles have been published on gamma-Chaconine.

Structure

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


  Mrv0541 02241215062D          

 40 46  0  0  0  0            999 V2000
   -1.1401   -3.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8923   -2.0818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3384   -1.4373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8427   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -1.0903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0991   -1.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4289   -1.4869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -0.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247   -0.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6683   -0.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5690    0.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8255    0.6441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315    0.1980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3875    0.5946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444    0.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8255   -1.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9247    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9657    2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7178    2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9743    3.1227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2220    2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247    2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4289    2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4 27  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 29  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
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 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 31 39  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 38  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END

HMDB0033678
     RDKit          3D
gamma-Chaconine
 93 99  0  0  0  0  0  0  0  0999 V2000
   -9.0121   -1.8541    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7586   -1.8888   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
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 40 93  1  0
M  END


  Mrv0541 02241215062D          

 40 46  0  0  0  0            999 V2000
   -1.1401   -3.5688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0991   -1.9330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496   -2.7757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1315   -1.6851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255   -1.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2630    0.7929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7178    1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2220    1.7843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247    1.3381    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9657    3.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7178    3.5688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2220    2.6765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9247    2.2304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4289    2.2304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 26  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4  5  1  0  0  0  0
  4 27  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 18  1  0  0  0  0
  7  8  1  0  0  0  0
  7 21  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 10 19  1  0  0  0  0
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 13 29  1  0  0  0  0
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 15 16  2  0  0  0  0
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 22 23  1  0  0  0  0
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 23 28  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
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 30 33  1  0  0  0  0
 31 32  1  0  0  0  0
 31 39  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 34 38  1  0  0  0  0
 35 36  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033678

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C33H53NO6/c1-17-5-8-24-18(2)27-25(34(24)15-17)14-23-21-7-6-19-13-20(9-11-32(19,3)22(21)10-12-33(23,27)4)39-31-30(38)29(37)28(36)26(16-35)40-31/h6,17-18,20-31,35-38H,5,7-16H2,1-4H3

> <INCHI_KEY>
IDGKMGZVTKHZDA-UHFFFAOYSA-N

> <FORMULA>
C33H53NO6

> <MOLECULAR_WEIGHT>
559.777

> <EXACT_MASS>
559.387288433

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
65.98895672355326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)oxane-3,4,5-triol

> <ALOGPS_LOGP>
2.96

> <JCHEM_LOGP>
2.3029511400172904

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.26913023185634

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.58551363574879

> <JCHEM_PKA_STRONGEST_BASIC>
12.019619056088574

> <JCHEM_POLAR_SURFACE_AREA>
102.62000000000002

> <JCHEM_REFRACTIVITY>
153.2707

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.05e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033678
     RDKit          3D
gamma-Chaconine
 93 99  0  0  0  0  0  0  0  0999 V2000
   -9.0121   -1.8541    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7586   -1.8888   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7189   -0.8150   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9246    0.3907   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4825   -0.0224   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6718    0.9379    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6579    1.9005    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465    0.1222    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2582   -1.3187    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744   -1.7497    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830   -0.4932    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206   -0.6702   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5331   -0.7235   -1.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.5255   -1.1669    1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1019   -0.2423    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.128  -6.662   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.498  -5.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.666  -3.886   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.498  -2.683   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.573  -1.480   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.093  -2.035   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.185  -3.608   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.093  -5.181   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.534  -2.776   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.979  -1.202   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.459  -1.665   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.847  -0.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.662   0.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.274   1.202   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.979   0.370   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.590   1.110   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.203   0.462   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.203  -1.110   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.590  -1.850   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.498  -3.331   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.295  -4.163   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.958  -2.405   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.570  -3.146   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.570  -4.719   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.274  -5.459   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.979  -4.719   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      -3.979  -3.146   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      -5.274  -2.313   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.958   1.480   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.940   3.331   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       6.014   3.331   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.459   2.498   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       7.403   4.163   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.940   4.996   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       7.403   5.829   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       6.940   6.662   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       5.552   5.829   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       6.014   4.996   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.459   4.163   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.534   4.163   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    3    6    8   21                                             
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   15   19                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   29                                                  
CONECT   14   13   15                                                       
CONECT   15   10   14   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    6   17   19                                                  
CONECT   19   10   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21    7   20                                                       
CONECT   22   23                                                            
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26    2   25   27                                                  
CONECT   27    4   26   28                                                  
CONECT   28   23   27                                                       
CONECT   29   13   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32   39                                                  
CONECT   32   31                                                            
CONECT   33   30   34                                                       
CONECT   34   33   35   38                                                  
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   38                                                            
CONECT   38   34   37   39                                                  
CONECT   39   31   38   40                                                  
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

COMPND    HMDB0033678
HETATM    1  C1  UNL     1      -9.012  -1.854   0.680  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.759  -1.889  -0.166  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.719  -0.815  -1.208  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.925   0.391  -0.705  1.00  0.00           C  
HETATM    5  C5  UNL     1      -5.483  -0.022  -0.558  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.672   0.938   0.265  1.00  0.00           C  
HETATM    7  C7  UNL     1      -5.658   1.901   0.940  1.00  0.00           C  
HETATM    8  C8  UNL     1      -4.047   0.122   1.337  1.00  0.00           C  
HETATM    9  C9  UNL     1      -4.258  -1.319   0.925  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.974  -1.750   0.205  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.183  -0.493   0.092  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.721  -0.670  -0.132  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.533  -0.723  -1.654  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.862  -0.519  -2.040  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.738   0.110  -1.284  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.119   0.265  -1.763  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.946   1.303  -1.112  1.00  0.00           C  
HETATM   18  O1  UNL     1       4.954   0.678  -0.360  1.00  0.00           O  
HETATM   19  C18 UNL     1       6.224   0.901  -0.839  1.00  0.00           C  
HETATM   20  O2  UNL     1       6.858  -0.268  -1.253  1.00  0.00           O  
HETATM   21  C19 UNL     1       7.130  -1.120  -0.191  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.755  -2.371  -0.776  1.00  0.00           C  
HETATM   23  O3  UNL     1       6.898  -3.000  -1.675  1.00  0.00           O  
HETATM   24  C21 UNL     1       8.193  -0.468   0.689  1.00  0.00           C  
HETATM   25  O4  UNL     1       9.261  -0.133  -0.128  1.00  0.00           O  
HETATM   26  C22 UNL     1       7.603   0.783   1.253  1.00  0.00           C  
HETATM   27  O5  UNL     1       6.665   0.531   2.256  1.00  0.00           O  
HETATM   28  C23 UNL     1       7.068   1.663   0.168  1.00  0.00           C  
HETATM   29  O6  UNL     1       8.141   2.251  -0.499  1.00  0.00           O  
HETATM   30  C24 UNL     1       3.248   2.340  -0.325  1.00  0.00           C  
HETATM   31  C25 UNL     1       1.819   2.126  -0.024  1.00  0.00           C  
HETATM   32  C26 UNL     1       1.406   0.684   0.050  1.00  0.00           C  
HETATM   33  C27 UNL     1       2.348  -0.000   1.050  1.00  0.00           C  
HETATM   34  C28 UNL     1      -0.002   0.515   0.468  1.00  0.00           C  
HETATM   35  C29 UNL     1      -0.881   1.718   0.278  1.00  0.00           C  
HETATM   36  C30 UNL     1      -2.017   1.605   1.307  1.00  0.00           C  
HETATM   37  C31 UNL     1      -2.537   0.215   1.382  1.00  0.00           C  
HETATM   38  C32 UNL     1      -2.081  -0.548   2.602  1.00  0.00           C  
HETATM   39  N1  UNL     1      -5.382  -1.314   0.038  1.00  0.00           N  
HETATM   40  C33 UNL     1      -6.559  -1.738   0.739  1.00  0.00           C  
HETATM   41  H1  UNL     1      -9.903  -2.187   0.108  1.00  0.00           H  
HETATM   42  H2  UNL     1      -8.862  -2.632   1.479  1.00  0.00           H  
HETATM   43  H3  UNL     1      -9.154  -0.897   1.193  1.00  0.00           H  
HETATM   44  H4  UNL     1      -7.763  -2.870  -0.701  1.00  0.00           H  
HETATM   45  H5  UNL     1      -7.289  -1.210  -2.150  1.00  0.00           H  
HETATM   46  H6  UNL     1      -8.748  -0.473  -1.413  1.00  0.00           H  
HETATM   47  H7  UNL     1      -7.397   0.679   0.254  1.00  0.00           H  
HETATM   48  H8  UNL     1      -6.978   1.157  -1.485  1.00  0.00           H  
HETATM   49  H9  UNL     1      -5.038  -0.059  -1.573  1.00  0.00           H  
HETATM   50  H10 UNL     1      -3.998   1.558  -0.324  1.00  0.00           H  
HETATM   51  H11 UNL     1      -6.192   1.387   1.739  1.00  0.00           H  
HETATM   52  H12 UNL     1      -6.300   2.397   0.191  1.00  0.00           H  
HETATM   53  H13 UNL     1      -5.087   2.738   1.437  1.00  0.00           H  
HETATM   54  H14 UNL     1      -4.420   0.334   2.354  1.00  0.00           H  
HETATM   55  H15 UNL     1      -4.460  -1.936   1.808  1.00  0.00           H  
HETATM   56  H16 UNL     1      -3.273  -2.107  -0.800  1.00  0.00           H  
HETATM   57  H17 UNL     1      -2.466  -2.533   0.807  1.00  0.00           H  
HETATM   58  H18 UNL     1      -2.618   0.112  -0.730  1.00  0.00           H  
HETATM   59  H19 UNL     1      -0.377  -1.606   0.317  1.00  0.00           H  
HETATM   60  H20 UNL     1      -1.136   0.132  -2.055  1.00  0.00           H  
HETATM   61  H21 UNL     1      -0.971  -1.672  -1.997  1.00  0.00           H  
HETATM   62  H22 UNL     1       1.197  -0.902  -2.995  1.00  0.00           H  
HETATM   63  H23 UNL     1       3.601  -0.755  -1.659  1.00  0.00           H  
HETATM   64  H24 UNL     1       3.071   0.398  -2.886  1.00  0.00           H  
HETATM   65  H25 UNL     1       4.517   1.833  -1.935  1.00  0.00           H  
HETATM   66  H26 UNL     1       6.162   1.551  -1.749  1.00  0.00           H  
HETATM   67  H27 UNL     1       6.228  -1.392   0.379  1.00  0.00           H  
HETATM   68  H28 UNL     1       8.020  -3.062   0.054  1.00  0.00           H  
HETATM   69  H29 UNL     1       8.702  -2.048  -1.272  1.00  0.00           H  
HETATM   70  H30 UNL     1       7.357  -3.793  -2.007  1.00  0.00           H  
HETATM   71  H31 UNL     1       8.525  -1.167   1.466  1.00  0.00           H  
HETATM   72  H32 UNL     1      10.102  -0.242   0.400  1.00  0.00           H  
HETATM   73  H33 UNL     1       8.444   1.348   1.746  1.00  0.00           H  
HETATM   74  H34 UNL     1       5.847   0.121   1.910  1.00  0.00           H  
HETATM   75  H35 UNL     1       6.444   2.439   0.630  1.00  0.00           H  
HETATM   76  H36 UNL     1       8.094   2.065  -1.475  1.00  0.00           H  
HETATM   77  H37 UNL     1       3.344   3.368  -0.789  1.00  0.00           H  
HETATM   78  H38 UNL     1       3.791   2.459   0.660  1.00  0.00           H  
HETATM   79  H39 UNL     1       1.191   2.613  -0.809  1.00  0.00           H  
HETATM   80  H40 UNL     1       1.564   2.590   0.972  1.00  0.00           H  
HETATM   81  H41 UNL     1       2.881  -0.846   0.606  1.00  0.00           H  
HETATM   82  H42 UNL     1       1.713  -0.445   1.873  1.00  0.00           H  
HETATM   83  H43 UNL     1       2.995   0.735   1.566  1.00  0.00           H  
HETATM   84  H44 UNL     1       0.010   0.318   1.582  1.00  0.00           H  
HETATM   85  H45 UNL     1      -0.406   2.676   0.458  1.00  0.00           H  
HETATM   86  H46 UNL     1      -1.342   1.715  -0.730  1.00  0.00           H  
HETATM   87  H47 UNL     1      -1.611   1.867   2.323  1.00  0.00           H  
HETATM   88  H48 UNL     1      -2.741   2.378   1.058  1.00  0.00           H  
HETATM   89  H49 UNL     1      -2.948  -0.991   3.176  1.00  0.00           H  
HETATM   90  H50 UNL     1      -1.587   0.124   3.360  1.00  0.00           H  
HETATM   91  H51 UNL     1      -1.445  -1.425   2.351  1.00  0.00           H  
HETATM   92  H52 UNL     1      -6.344  -2.761   1.145  1.00  0.00           H  
HETATM   93  H53 UNL     1      -6.778  -1.105   1.608  1.00  0.00           H  
CONECT    1    2   41   42   43
CONECT    2    3   40   44
CONECT    3    4   45   46
CONECT    4    5   47   48
CONECT    5    6   39   49
CONECT    6    7    8   50
CONECT    7   51   52   53
CONECT    8    9   37   54
CONECT    9   10   39   55
CONECT   10   11   56   57
CONECT   11   12   37   58
CONECT   12   13   34   59
CONECT   13   14   60   61
CONECT   14   15   15   62
CONECT   15   16   32
CONECT   16   17   63   64
CONECT   17   18   30   65
CONECT   18   19
CONECT   19   20   28   66
CONECT   20   21
CONECT   21   22   24   67
CONECT   22   23   68   69
CONECT   23   70
CONECT   24   25   26   71
CONECT   25   72
CONECT   26   27   28   73
CONECT   27   74
CONECT   28   29   75
CONECT   29   76
CONECT   30   31   77   78
CONECT   31   32   79   80
CONECT   32   33   34
CONECT   33   81   82   83
CONECT   34   35   84
CONECT   35   36   85   86
CONECT   36   37   87   88
CONECT   37   38
CONECT   38   89   90   91
CONECT   39   40
CONECT   40   92   93
END

HMDB0033678
     RDKit          3D
gamma-Chaconine
 93 99  0  0  0  0  0  0  0  0999 V2000
   -9.0121   -1.8541    0.6801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7586   -1.8888   -0.1656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7189   -0.8150   -1.2077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9246    0.3907   -0.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4825   -0.0224   -0.5578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6718    0.9379    0.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6579    1.9005    0.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465    0.1222    1.3373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2582   -1.3187    0.9249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9744   -1.7497    0.2052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1830   -0.4932    0.0921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7206   -0.6702   -0.1319 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5331   -0.7235   -1.6535 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8616   -0.5187   -2.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7379    0.1101   -1.2845 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1185    0.2645   -1.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9464    1.3029   -1.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9536    0.6784   -0.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2238    0.9009   -0.8389 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -0.2679   -1.2528 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1304   -1.1198   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7552   -2.3710   -0.7761 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8984   -3.0002   -1.6751 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1926   -0.4676    0.6894 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2613   -0.1333   -0.1275 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6027    0.7832    1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6654    0.5313    2.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0682    1.6628    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1408    2.2506   -0.4987 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2478    2.3399   -0.3250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8185    2.1264   -0.0245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4061    0.6837    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3476   -0.0003    1.0500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.5147    0.4684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8811    1.7178    0.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0171    1.6050    1.3070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5367    0.2153    1.3818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0806   -0.5479    2.6025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3816   -1.3142    0.0375 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5587   -1.7382    0.7392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9033   -2.1868    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8625   -2.6323    1.4786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1544   -0.8973    1.1927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7634   -2.8701   -0.7012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2893   -1.2096   -2.1502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7475   -0.4733   -1.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3974    0.6790    0.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9776    1.1570   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0381   -0.0595   -1.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9975    1.5581   -0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1921    1.3875    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2999    2.3973    0.1905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0873    2.7383    1.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4202    0.3336    2.3540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4598   -1.9365    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2733   -2.1070   -0.7996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4664   -2.5331    0.8069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6182    0.1121   -0.7298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3766   -1.6061    0.3169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1359    0.1323   -2.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9709   -1.6719   -1.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1965   -0.9020   -2.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006   -0.7546   -1.6587 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0711    0.3981   -2.8864 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5169    1.8332   -1.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1619    1.5509   -1.7485 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2278   -1.3917    0.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0197   -3.0621    0.0536 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7025   -2.0484   -1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3573   -3.7935   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5255   -1.1669    1.4661 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1019   -0.2423    0.4003 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4442    1.3477    1.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8466    0.1208    1.9097 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4437    2.4390    0.6302 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0942    2.0650   -1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3436    3.3678   -0.7891 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7914    2.4588    0.6602 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1905    2.6134   -0.8086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5641    2.5902    0.9716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8810   -0.8458    0.6059 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7128   -0.4448    1.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9946    0.7353    1.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103    0.3176    1.5825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4057    2.6764    0.4580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3417    1.7150   -0.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6108    1.8675    2.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7414    2.3778    1.0582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483   -0.9911    3.1762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5868    0.1236    3.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449   -1.4254    2.3512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3441   -2.7609    1.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7784   -1.1049    1.6082 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
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Chaconine	Generator
Γ-chaconine	Generator
beta-D-Glucopyranoside, (3beta)-solanid-5-en-3-yl	HMDB
gamma-Chaconine	MeSH

Chemical Formula

C₃₃H₅₃NO₆

Average Molecular Weight

559.777

Monoisotopic Molecular Weight

559.387288433

IUPAC Name

2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)oxane-3,4,5-triol

Traditional Name

2-(hydroxymethyl)-6-({10,14,16,20-tetramethyl-22-azahexacyclo[12.10.0.0²,¹¹.0⁵,¹⁰.0¹⁵,²³.0¹⁷,²²]tetracos-4-en-7-yl}oxy)oxane-3,4,5-triol

CAS Registry Number

511-36-4

SMILES

CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C33H53NO6/c1-17-5-8-24-18(2)27-25(34(24)15-17)14-23-21-7-6-19-13-20(9-11-32(19,3)22(21)10-12-33(23,27)4)39-31-30(38)29(37)28(36)26(16-35)40-31/h6,17-18,20-31,35-38H,5,7-16H2,1-4H3

InChI Key

IDGKMGZVTKHZDA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroidal saponins. These are saponins in which the aglycone moiety is a steroid. The steroidal aglycone is usually a spirostane, furostane, spirosolane, solanidane, or curcubitacin derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal saponins

Alternative Parents

Substituents

Steroidal saponin
Diterpene glycoside
Solanidane skeleton
Diterpenoid
Steroidal alkaloid
Azasteroid
Delta-5-steroid
Terpene glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Alkaloid or derivatives
Indolizidine
Monosaccharide
N-alkylpyrrolidine
Oxane
Piperidine
Pyrrolidine
Tertiary amine
Tertiary aliphatic amine
Secondary alcohol
Polyol
Oxacycle
Azacycle
Acetal
Organoheterocyclic compound
Primary alcohol
Alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Amine
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0033678)
Membrane (HMDB: HMDB0033678)

Source

Endogenous

Endogenous (HMDB: HMDB0033678)

Exogenous

Exogenous (HMDB: HMDB0033678)

Food

Vegetable

Tuber

Potato (FooDB: FOOD00175)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	243 - 244 °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	0.02 g/L	ALOGPS
logP	2.96	ALOGPS
logP	2.3	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	12.02	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.62 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	153.27 m³·mol⁻¹	ChemAxon
Polarizability	65.99 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	226.147	31661259
DarkChem	[M-H]-	220.178	31661259
DeepCCS	[M-2H]-	264.881	30932474
DeepCCS	[M+Na]+	240.448	30932474
AllCCS	[M+H]+	235.9	32859911
AllCCS	[M+H-H2O]+	234.9	32859911
AllCCS	[M+NH4]+	236.9	32859911
AllCCS	[M+Na]+	237.2	32859911
AllCCS	[M-H]-	216.3	32859911
AllCCS	[M+Na-2H]-	219.5	32859911
AllCCS	[M+HCOO]-	223.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.46 minutes	32390414
Predicted by Siyang on May 30, 2022	13.0219 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.3 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	123.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2706.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	158.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	210.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	467.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	599.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	316.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1019.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	542.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1464.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	307.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	305.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	311.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	25.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
gamma-Chaconine	CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(O)C1O	3117.9	Standard polar	33892256
gamma-Chaconine	CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(O)C1O	3503.8	Standard non polar	33892256
gamma-Chaconine	CC1C2CCC(C)CN2C2CC3C4CC=C5CC(CCC5(C)C4CCC3(C)C12)OC1OC(CO)C(O)C(O)C1O	4479.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
gamma-Chaconine,1TMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4568.4	Semi standard non polar	33892256
gamma-Chaconine,1TMS,isomer #2	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4553.1	Semi standard non polar	33892256
gamma-Chaconine,1TMS,isomer #3	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O[Si](C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4529.3	Semi standard non polar	33892256
gamma-Chaconine,1TMS,isomer #4	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4541.7	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4524.2	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #2	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4501.5	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #3	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O)C(O)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4524.7	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #4	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4472.2	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #5	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C)C(O)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4486.6	Semi standard non polar	33892256
gamma-Chaconine,2TMS,isomer #6	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O[Si](C)(C)C)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4475.2	Semi standard non polar	33892256
gamma-Chaconine,3TMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4468.6	Semi standard non polar	33892256
gamma-Chaconine,3TMS,isomer #2	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4474.2	Semi standard non polar	33892256
gamma-Chaconine,3TMS,isomer #3	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4460.2	Semi standard non polar	33892256
gamma-Chaconine,3TMS,isomer #4	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4445.8	Semi standard non polar	33892256
gamma-Chaconine,4TMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C7O[Si](C)(C)C)CCC6(C)C5CCC43C)N2C1	4448.1	Semi standard non polar	33892256
gamma-Chaconine,1TBDMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4801.0	Semi standard non polar	33892256
gamma-Chaconine,1TBDMS,isomer #2	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4773.0	Semi standard non polar	33892256
gamma-Chaconine,1TBDMS,isomer #3	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4738.8	Semi standard non polar	33892256
gamma-Chaconine,1TBDMS,isomer #4	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O)C7O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC43C)N2C1	4760.7	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #1	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C7O)CCC6(C)C5CCC43C)N2C1	4937.6	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #2	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4911.6	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #3	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C7O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC43C)N2C1	4941.2	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #4	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C7O)CCC6(C)C5CCC43C)N2C1	4877.5	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #5	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C7O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC43C)N2C1	4893.4	Semi standard non polar	33892256
gamma-Chaconine,2TBDMS,isomer #6	CC1CCC2C(C)C3C(CC4C5CC=C6CC(OC7OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C7O[Si](C)(C)C(C)(C)C)CCC6(C)C5CCC43C)N2C1	4883.3	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 - gamma-Chaconine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001l-5706290000-7796ea497aa55a7c8d24	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (1 TMS) - 70eV, Positive	splash10-0uxr-3515109000-95ade113db6bab299668	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS ("gamma-Chaconine,1TMS,#1" TMS) - 70eV, Positive	Not Available	2021-10-14	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-15	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - gamma-Chaconine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-15	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 - gamma-Chaconine 10V, Positive-QTOF	splash10-01pk-0009050000-796f12880c58ff47c113	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 20V, Positive-QTOF	splash10-000t-0119000000-f9ac3621f3b0f176a0b5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 40V, Positive-QTOF	splash10-014j-0529000000-e86569cbae326820c5cc	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 10V, Negative-QTOF	splash10-0a4j-1208090000-8630d1bacf1b12ae82ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 20V, Negative-QTOF	splash10-0002-1209010000-08108d87392bfc9377fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 40V, Negative-QTOF	splash10-000w-5009000000-d41a00e749afd523bbe1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 10V, Positive-QTOF	splash10-03di-0000090000-50b0bd514100ca2eeece	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 20V, Positive-QTOF	splash10-001j-0119230000-cce2dfe30ad20dce590f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 40V, Positive-QTOF	splash10-08g4-4201900000-ff87aa7f355eeddf8bca	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 10V, Negative-QTOF	splash10-0a4i-0000090000-8d1f177d2258a4e299ac	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 20V, Negative-QTOF	splash10-0a4i-7106090000-05798f8ede9f30288552	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - gamma-Chaconine 40V, Negative-QTOF	splash10-0a4i-9003010000-c6b4b2772e3a7ebd41d8	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB011805

KNApSAcK ID

C00034522

Chemspider ID

26503509

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12302826

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

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 gamma-Chaconine (HMDB0033678)

MOL for HMDB0033678 (gamma-Chaconine)

3D MOL for HMDB0033678 (gamma-Chaconine)

3D SDF for HMDB0033678 (gamma-Chaconine)

3D-SDF for HMDB0033678 (gamma-Chaconine)

PDB for HMDB0033678 (gamma-Chaconine)

3D PDB for HMDB0033678 (gamma-Chaconine)

SMILES for HMDB0033678 (gamma-Chaconine)

INCHI for HMDB0033678 (gamma-Chaconine)

Structure for HMDB0033678 (gamma-Chaconine)

3D Structure for HMDB0033678 (gamma-Chaconine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra