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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:15:53 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037022

Secondary Accession Numbers

HMDB37022

Metabolite Identification

Common Name

Cichoralexin

Description

Cichoralexin belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Cichoralexin.

Structure

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

HMDB0037022
     RDKit          3D
Cichoralexin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.0801    3.0789    0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.7819    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464    1.5168   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.1581   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.4677   -0.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983   -0.3687   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -1.7398   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8783    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -1.9376    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.4777   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.0888   -1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    0.1048   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.7129    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.5389   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    2.4178   -0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4307    1.6854    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298    0.9734   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    0.5881    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596    3.8134    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    2.9991    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    3.4911    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692    2.2143    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -0.2985   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930   -2.5080   -0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.0421    1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -2.8163    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304   -1.9214    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -3.0632    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -1.5600    1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -2.1512   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2355   -1.7134   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670    0.1513   -2.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.0773   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -0.2614    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -0.6149    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -1.7765    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069    1.7595   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486    0.2026    1.2122 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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061309312D          

 18 20  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8656    0.6356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6412    0.6356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  1  1  0  0  0  0
  7  4  1  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 10  5  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16 11  2  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037022

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6-7,9-10,12-14H,4-5H2,1-3H3

> <INCHI_KEY>
FJKWKEZAHVWIOR-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.44124946967596

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.6598072566666664

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.912116876634745

> <JCHEM_PKA_STRONGEST_BASIC>
-4.977939587996042

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
68.107

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethyl-3H,3aH,4H,5H,6H,6aH,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037022
     RDKit          3D
Cichoralexin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.0801    3.0789    0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.7819    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464    1.5168   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.1581   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.4677   -0.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983   -0.3687   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -1.7398   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8783    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -1.9376    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.4777   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.0888   -1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    0.1048   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.7129    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.5389   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    2.4178   -0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4307    1.6854    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298    0.9734   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    0.5881    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596    3.8134    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    2.9991    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    3.4911    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692    2.2143    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -0.2985   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930   -2.5080   -0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.0421    1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -2.8163    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304   -1.9214    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -3.0632    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -1.5600    1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -2.1512   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2355   -1.7134   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670    0.1513   -2.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.0773   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -0.2614    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -0.6149    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -1.7765    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069    1.7595   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486    0.2026    1.2122 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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  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       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.616   1.186   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.530   1.186   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    7                                                       
CONECT    5    4   10                                                       
CONECT    6    8   11                                                       
CONECT    7    1    4   12                                                  
CONECT    8    2    6   13                                                  
CONECT    9    3   10   15                                                  
CONECT   10    5    9   14                                                  
CONECT   11    6   12   16                                                  
CONECT   12    7   11   13                                                  
CONECT   13    8   12   14                                                  
CONECT   14   10   13   18                                                  
CONECT   15    9   17   18                                                  
CONECT   16   11                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0037022
HETATM    1  C1  UNL     1      -1.080   3.079   0.936  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.526   1.782   0.382  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.746   1.517  -0.017  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.855   0.158  -0.507  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.906  -0.468  -0.781  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.498  -0.369  -0.630  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.300  -1.740  -0.076  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.050  -1.878   1.214  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.202  -1.938   0.120  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.894  -1.478  -1.091  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.357  -0.089  -1.167  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.787   0.105  -0.648  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.046  -0.713   0.583  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.730   1.539  -0.237  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.629   2.418  -0.329  1.00  0.00           O  
HETATM   16  O3  UNL     1       1.431   1.685   0.282  1.00  0.00           O  
HETATM   17  C14 UNL     1       0.530   0.973  -0.583  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.662   0.588   0.194  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.960   3.813   0.112  1.00  0.00           H  
HETATM   20  H2  UNL     1      -0.115   2.999   1.484  1.00  0.00           H  
HETATM   21  H3  UNL     1      -1.807   3.491   1.683  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.569   2.214   0.013  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.202  -0.299  -1.695  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.693  -2.508  -0.776  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.906  -1.042   1.915  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.815  -2.816   1.755  1.00  0.00           H  
HETATM   27  H9  UNL     1      -3.130  -1.921   0.970  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.318  -3.063   0.181  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.560  -1.560   1.077  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.789  -2.151  -1.260  1.00  0.00           H  
HETATM   31  H13 UNL     1       0.236  -1.713  -1.980  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.467   0.151  -2.273  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.539  -0.077  -1.414  1.00  0.00           H  
HETATM   34  H16 UNL     1       2.542  -0.261   1.452  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.146  -0.615   0.792  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.860  -1.776   0.434  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.207   1.759  -1.329  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.449   0.203   1.212  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   18
CONECT    3    4   22
CONECT    4    5    5    6
CONECT    6    7   18   23
CONECT    7    8    9   24
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   17   32
CONECT   12   13   14   33
CONECT   13   34   35   36
CONECT   14   15   15   16
CONECT   16   17
CONECT   17   18   37
CONECT   18   38
END

HMDB0037022
     RDKit          3D
Cichoralexin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.0801    3.0789    0.9361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5256    1.7819    0.3819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7464    1.5168   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549    0.1581   -0.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9061   -0.4677   -0.7811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4983   -0.3687   -0.6298 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3000   -1.7398   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0501   -1.8783    1.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2017   -1.9376    0.1201 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8945   -1.4777   -1.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3568   -0.0888   -1.1672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7874    0.1048   -0.6480 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0458   -0.7129    0.5833 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7302    1.5389   -0.2369 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6286    2.4178   -0.3293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4307    1.6854    0.2824 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5298    0.9734   -0.5827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6620    0.5881    0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9596    3.8134    0.1125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1148    2.9991    1.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    3.4911    1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5692    2.2143    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2021   -0.2985   -1.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6930   -2.5080   -0.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9061   -1.0421    1.9145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8150   -2.8163    1.7554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1304   -1.9214    0.9700 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3181   -3.0632    0.1815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5599   -1.5600    1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7886   -2.1512   -1.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2355   -1.7134   -1.9795 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4670    0.1513   -2.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5388   -0.0773   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5418   -0.2614    1.4517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1464   -0.6149    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8604   -1.7765    0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2069    1.7595   -1.3292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486    0.2026    1.2122 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
 12 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  6  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Carpesia lactone	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

3,6,9-trimethyl-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

Traditional Name

3,6,9-trimethyl-3H,3aH,4H,5H,6H,6aH,9aH,9bH-azuleno[4,5-b]furan-2,7-dione

CAS Registry Number

132296-37-8

SMILES

CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O

InChI Identifier

InChI=1S/C15H20O3/c1-7-4-5-10-9(3)15(17)18-14(10)13-8(2)6-11(16)12(7)13/h6-7,9-10,12-14H,4-5H2,1-3H3

InChI Key

FJKWKEZAHVWIOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organooxygen compound
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037022)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037022)

Source

Endogenous

Endogenous (HMDB: HMDB0037022)

Plant

Plant (HMDB: HMDB0037022)

Animal

Animal (HMDB: HMDB0037022)

Exogenous

Food

Food (HMDB: HMDB0037022)

Vegetable

Root vegetable

Chicory (FooDB: FOOD00049)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037022)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037022)

Cellular process

Cell signaling (HMDB: HMDB0037022)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037022)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037022)

Nutrient

Nutrient (HMDB: HMDB0037022)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037022)

Emulsifier (HMDB: HMDB0037022)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	145 - 146 °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	0.28 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.66	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	15.91	ChemAxon
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.11 m³·mol⁻¹	ChemAxon
Polarizability	27.44 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	158.158	31661259
DarkChem	[M-H]-	153.683	31661259
DeepCCS	[M+H]+	165.721	30932474
DeepCCS	[M-H]-	163.363	30932474
DeepCCS	[M-2H]-	196.696	30932474
DeepCCS	[M+Na]+	172.104	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	160.9	32859911
AllCCS	[M+Na]+	161.9	32859911
AllCCS	[M-H]-	164.0	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cichoralexin	CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O	2966.0	Standard polar	33892256
Cichoralexin	CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O	2011.0	Standard non polar	33892256
Cichoralexin	CC1C2CCC(C)C3C(C2OC1=O)C(C)=CC3=O	2175.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cichoralexin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(C)CCC3C(C)C(=O)OC3C12	2194.3	Semi standard non polar	33892256
Cichoralexin,1TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=C2C(C)CCC3C(C)C(=O)OC3C12	2051.3	Standard non polar	33892256
Cichoralexin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(C)CCC3C(C)C(=O)OC3C12	2392.4	Semi standard non polar	33892256
Cichoralexin,1TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(C)CCC3C(C)C(=O)OC3C12	2294.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cichoralexin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-9870000000-22437ede758350e45b6b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cichoralexin 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 - Cichoralexin 10V, Positive-QTOF	splash10-0002-0290000000-702a995926cd99706c4e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 20V, Positive-QTOF	splash10-0032-1970000000-f6a95e91013309674f64	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 40V, Positive-QTOF	splash10-0a4i-9800000000-455f1856d23ce7f26a21	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 10V, Negative-QTOF	splash10-0002-0090000000-b8579944992ae1b57404	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 20V, Negative-QTOF	splash10-0f6t-0190000000-8c513e252a133fddb263	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 40V, Negative-QTOF	splash10-114j-5910000000-72fabb7f1c1e5687c146	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 10V, Negative-QTOF	splash10-0002-0090000000-717909ee4df9ba3b89f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 20V, Negative-QTOF	splash10-0002-0190000000-c41d861087afed3c0ac9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 40V, Negative-QTOF	splash10-00bd-2960000000-bede17322bf322bf9fbf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 10V, Positive-QTOF	splash10-0002-0090000000-fab2e65b71aa23cc527f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 20V, Positive-QTOF	splash10-001j-0390000000-503406b32624c89fe436	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cichoralexin 40V, Positive-QTOF	splash10-004i-8910000000-b4a45e473036a835b788	2021-09-22	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

FDB016002

KNApSAcK ID

C00055002

Chemspider ID

4474960

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315718

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 Cichoralexin (HMDB0037022)

MOL for HMDB0037022 (Cichoralexin)

3D MOL for HMDB0037022 (Cichoralexin)

3D SDF for HMDB0037022 (Cichoralexin)

3D-SDF for HMDB0037022 (Cichoralexin)

PDB for HMDB0037022 (Cichoralexin)

3D PDB for HMDB0037022 (Cichoralexin)

SMILES for HMDB0037022 (Cichoralexin)

INCHI for HMDB0037022 (Cichoralexin)

Structure for HMDB0037022 (Cichoralexin)

3D Structure for HMDB0037022 (Cichoralexin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra