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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:48:37 UTC

Update Date

2022-03-07 02:55:23 UTC

HMDB ID

HMDB0037559

Secondary Accession Numbers

HMDB37559

Metabolite Identification

Common Name

Cadabicilone

Description

Cadabicilone belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Based on a literature review a small amount of articles have been published on Cadabicilone.

Structure

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

HMDB0037559
     RDKit          3D
Cadabicilone
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.8330   -0.4005   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    0.3010    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    1.7375    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328    2.5670   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    1.9246    0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7899    0.6635   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6252   -0.2270    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.6273    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920   -1.9406    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -0.9581   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -1.2879   -1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -1.2897    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583   -0.1111    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.1022    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268    1.9064   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3817   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857    2.8300   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    0.4697    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8867   -0.4800   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    0.2630   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -1.4196   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    0.3637    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.4277   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614   -0.0574    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -2.2937    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5485   -1.8783   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -1.9910    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789   -2.9328    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -1.2455   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7205   -0.7443   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -2.3747   -1.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163   -1.9763    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9907   -1.8799   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369   -0.3586    0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2045    0.0647    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524    1.2215   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4780    3.1478   -1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004    3.4637   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    2.9891    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.6491    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061309512D          

 18 20  0  0  0  0            999 V2000
    4.2295   -0.5732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4944    1.8665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7591   -1.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083   -0.9642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995   -0.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983   -0.2372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.4640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547    1.8150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    1.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963    1.0941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 15  3  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  2  0  0  0  0
 17 14  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037559

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3

> <INCHI_KEY>
BXRGGUXPWTWACZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.926123939118572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.718669615333334

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.374575634746893

> <JCHEM_PKA_STRONGEST_BASIC>
-6.916422262291207

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
67.2068

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037559
     RDKit          3D
Cadabicilone
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.8330   -0.4005   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    0.3010    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    1.7375    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328    2.5670   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    1.9246    0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7899    0.6635   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6252   -0.2270    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.6273    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920   -1.9406    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -0.9581   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -1.2879   -1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -1.2897    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583   -0.1111    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.1022    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268    1.9064   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3817   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857    2.8300   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    0.4697    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8867   -0.4800   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    0.2630   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -1.4196   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    0.3637    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.4277   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614   -0.0574    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -2.2937    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5485   -1.8783   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -1.9910    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789   -2.9328    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -1.2455   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7205   -0.7443   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -2.3747   -1.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163   -1.9763    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9907   -1.8799   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369   -0.3586    0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2045    0.0647    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524    1.2215   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4780    3.1478   -1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004    3.4637   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    2.9891    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.6491    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 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       7.895  -1.070   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.790   3.484   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.417  -1.896   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495  -1.800   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.206   0.722   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.956  -1.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.606  -0.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.719  -0.076   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.062   2.127   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.223  -0.443   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.522   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.873   0.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.412   0.866   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.832   1.460   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.145  -0.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.289   3.388   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.141   2.271   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.406   2.042   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    4   15                                                       
CONECT    7    5   15                                                       
CONECT    8    1   10   14                                                  
CONECT    9    2   11   12                                                  
CONECT   10    4    8   13                                                  
CONECT   11    5    9   16                                                  
CONECT   12    9   13   15                                                  
CONECT   13   10   12   18                                                  
CONECT   14    8   17   18                                                  
CONECT   15    3    6    7   12                                             
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0037559
HETATM    1  C1  UNL     1      -3.833  -0.401  -0.437  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.981   0.301   0.550  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.716   1.738   0.179  1.00  0.00           C  
HETATM    4  O1  UNL     1      -3.633   2.567  -0.020  1.00  0.00           O  
HETATM    5  O2  UNL     1      -1.323   1.925   0.111  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.790   0.664  -0.181  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.625  -0.227   0.751  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.370  -1.627   0.361  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.092  -1.941   0.645  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.025  -0.958  -0.032  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.960  -1.288  -1.529  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.420  -1.290   0.415  1.00  0.00           C  
HETATM   13  C11 UNL     1       3.258  -0.111   0.785  1.00  0.00           C  
HETATM   14  C12 UNL     1       2.942   1.102   0.018  1.00  0.00           C  
HETATM   15  O3  UNL     1       3.827   1.906  -0.201  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.588   1.382  -0.496  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.186   2.830  -0.267  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.628   0.470   0.225  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.887  -0.480  -0.037  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.949   0.263  -1.343  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.536  -1.420  -0.694  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.511   0.364   1.540  1.00  0.00           H  
HETATM   23  H5  UNL     1      -0.997   0.428  -1.241  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.261  -0.057   1.774  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.951  -2.294   1.059  1.00  0.00           H  
HETATM   26  H8  UNL     1      -1.548  -1.878  -0.688  1.00  0.00           H  
HETATM   27  H9  UNL     1       0.280  -1.991   1.722  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.279  -2.933   0.140  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.053  -1.245  -1.923  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.720  -0.744  -2.103  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.267  -2.375  -1.582  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.416  -1.976   1.313  1.00  0.00           H  
HETATM   33  H15 UNL     1       2.991  -1.880  -0.359  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.337  -0.359   0.609  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.204   0.065   1.900  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.552   1.222  -1.589  1.00  0.00           H  
HETATM   37  H19 UNL     1       0.478   3.148  -1.067  1.00  0.00           H  
HETATM   38  H20 UNL     1       2.100   3.464  -0.309  1.00  0.00           H  
HETATM   39  H21 UNL     1       0.700   2.989   0.698  1.00  0.00           H  
HETATM   40  H22 UNL     1       0.714   0.649   1.305  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    7   22
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   23
CONECT    7    8   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   18
CONECT   11   29   30   31
CONECT   12   13   32   33
CONECT   13   14   34   35
CONECT   14   15   15   16
CONECT   16   17   18   36
CONECT   17   37   38   39
CONECT   18   40
END

HMDB0037559
     RDKit          3D
Cadabicilone
 40 42  0  0  0  0  0  0  0  0999 V2000
   -3.8330   -0.4005   -0.4369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9814    0.3010    0.5500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    1.7375    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6328    2.5670   -0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    1.9246    0.1115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7899    0.6635   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6252   -0.2270    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3704   -1.6273    0.3608 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0920   -1.9406    0.6450 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0254   -0.9581   -0.0316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9596   -1.2879   -1.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4198   -1.2897    0.4153 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2583   -0.1111    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9417    1.1022    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8268    1.9064   -0.2009 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5882    1.3817   -0.4960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857    2.8300   -0.2670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6285    0.4697    0.2250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8867   -0.4800   -0.0365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9489    0.2630   -1.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -1.4196   -0.6944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5110    0.3637    1.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9975    0.4277   -1.2413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2614   -0.0574    1.7738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9511   -2.2937    1.0591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5485   -1.8783   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2805   -1.9910    1.7215 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2789   -2.9328    0.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0535   -1.2455   -1.9232 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7205   -0.7443   -2.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671   -2.3747   -1.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163   -1.9763    1.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9907   -1.8799   -0.3591 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369   -0.3586    0.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2045    0.0647    1.8999 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5524    1.2215   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4780    3.1478   -1.0671 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1004    3.4637   -0.3090 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7000    2.9891    0.6981 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7143    0.6491    1.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 16 18  1  0
  7  2  1  0
 18 10  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 16 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

3,5a,9-trimethyl-dodecahydronaphtho[1,2-b]furan-2,8-dione

Traditional Name

3,5a,9-trimethyl-octahydro-3H-naphtho[1,2-b]furan-2,8-dione

CAS Registry Number

14804-47-8

SMILES

CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O

InChI Identifier

InChI=1S/C15H22O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h8-10,12-13H,4-7H2,1-3H3

InChI Key

BXRGGUXPWTWACZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Eudesmanolides, secoeudesmanolides, and derivatives

Alternative Parents

Substituents

Eudesmanolide
Sesquiterpenoid
Naphthofuran
Gamma butyrolactone
Tetrahydrofuran
Cyclic ketone
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037559)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037559)

Source

Endogenous

Endogenous (HMDB: HMDB0037559)

Plant

Plant (HMDB: HMDB0037559)

Animal

Animal (HMDB: HMDB0037559)

Exogenous

Food

Food (HMDB: HMDB0037559)

Fruit

Fruits (FooDB: FOOD00871)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037559)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037559)

Cellular process

Cell signaling (HMDB: HMDB0037559)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037559)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037559)

Nutrient

Nutrient (HMDB: HMDB0037559)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037559)

Emulsifier (HMDB: HMDB0037559)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 120 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	902.3 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	0.26 g/L	ALOGPS
logP	1.95	ALOGPS
logP	2.72	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	19.37	ChemAxon
pKa (Strongest Basic)	-6.9	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	67.21 m³·mol⁻¹	ChemAxon
Polarizability	27.93 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]+	158.516	31661259
DarkChem	[M-H]-	156.432	31661259
DeepCCS	[M+H]+	159.077	30932474
DeepCCS	[M-H]-	156.719	30932474
DeepCCS	[M-2H]-	190.0	30932474
DeepCCS	[M+Na]+	165.17	30932474
AllCCS	[M+H]+	158.9	32859911
AllCCS	[M+H-H2O]+	155.3	32859911
AllCCS	[M+NH4]+	162.3	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	166.1	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cadabicilone	CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O	2710.0	Standard polar	33892256
Cadabicilone	CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O	2043.1	Standard non polar	33892256
Cadabicilone	CC1C2CCC3(C)CCC(=O)C(C)C3C2OC1=O	2128.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cadabicilone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12	2170.5	Semi standard non polar	33892256
Cadabicilone,1TMS,isomer #1	CC1=C(O[Si](C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12	2066.2	Standard non polar	33892256
Cadabicilone,1TMS,isomer #2	CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C21	2162.9	Semi standard non polar	33892256
Cadabicilone,1TMS,isomer #2	CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C)C(C)C21	2022.5	Standard non polar	33892256
Cadabicilone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12	2385.5	Semi standard non polar	33892256
Cadabicilone,1TBDMS,isomer #1	CC1=C(O[Si](C)(C)C(C)(C)C)CCC2(C)CCC3C(C)C(=O)OC3C12	2327.3	Standard non polar	33892256
Cadabicilone,1TBDMS,isomer #2	CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21	2392.0	Semi standard non polar	33892256
Cadabicilone,1TBDMS,isomer #2	CC1C(=O)OC2C1CCC1(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)C21	2236.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cadabicilone GC-MS (Non-derivatized) - 70eV, Positive	splash10-009f-2960000000-0f725431c374e162b182	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cadabicilone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cadabicilone 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 - Cadabicilone 10V, Positive-QTOF	splash10-0udi-0390000000-ef79242d3d8ed92df432	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOF	splash10-0udi-0960000000-0e31a2abe3fc23ef704a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOF	splash10-014l-9300000000-18f7baac75a5bf82d828	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOF	splash10-0002-0090000000-9b15449c1771ca1ca357	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOF	splash10-052b-0190000000-db53a1d787fa4bc45630	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOF	splash10-0udi-7930000000-365fbba38169a90c6914	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Positive-QTOF	splash10-001i-0290000000-754dd18a87ade78d631c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Positive-QTOF	splash10-0ka9-0970000000-7c888b536a8ea7e866ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Positive-QTOF	splash10-056r-1900000000-0548aa46854407ab988f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 10V, Negative-QTOF	splash10-0002-0090000000-09b8c5776dceef2c388e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 20V, Negative-QTOF	splash10-0002-0190000000-181a6ad7f7eb4f01b276	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cadabicilone 40V, Negative-QTOF	splash10-000b-1930000000-511b9486ec0e22ae8c73	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

FDB016641

KNApSAcK ID

C00054320

Chemspider ID

288033

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

325292

PDB ID

Not Available

ChEBI ID

174307

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1862041

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 Cadabicilone (HMDB0037559)

MOL for HMDB0037559 (Cadabicilone)

3D MOL for HMDB0037559 (Cadabicilone)

3D SDF for HMDB0037559 (Cadabicilone)

3D-SDF for HMDB0037559 (Cadabicilone)

PDB for HMDB0037559 (Cadabicilone)

3D PDB for HMDB0037559 (Cadabicilone)

SMILES for HMDB0037559 (Cadabicilone)

INCHI for HMDB0037559 (Cadabicilone)

Structure for HMDB0037559 (Cadabicilone)

3D Structure for HMDB0037559 (Cadabicilone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra