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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:05:28 UTC

Update Date

2022-03-07 02:54:23 UTC

HMDB ID

HMDB0035146

Secondary Accession Numbers

HMDB35146

Metabolite Identification

Common Name

Aristolene

Description

Aristolene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton. Based on a literature review a small amount of articles have been published on Aristolene.

Structure

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

HMDB0035146
     RDKit          3D
Aristolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7482    2.4090    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    1.0417   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    0.5538    0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0870   -0.5317    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590   -1.4875   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883   -1.3324   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952   -2.3275    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -2.1424    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3300   -0.6960    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.0226   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    0.3929    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.6337    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.0418    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -0.0011   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -0.0634   -2.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    3.2188   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    2.5959    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    2.6470   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830    1.1849   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.3216    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8289    1.4292    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066   -0.0815   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5492   -1.0634    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -1.2949   -1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -2.5224   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -3.2769    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -2.7473    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606   -2.3567   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.5106    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6027   -0.5111   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.6471    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    2.5420    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    1.5900    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757   -0.4100   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230    0.9123    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -0.7595    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077    0.7241   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    0.2637   -2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -1.0555   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 14  2  1  0
 14  6  1  0
 11  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

  Mrv0541 05061308152D          

 15 17  0  0  0  0            999 V2000
    0.6556    3.1641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2612    1.7425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5078    2.7574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1474    2.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8196    1.5554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4917    2.3124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3278    0.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9835    0.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    0.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3278    2.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    0.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1308    1.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6391    1.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4587    1.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8196    1.7446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035146

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2=CCC3C(C3(C)C)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3

> <INCHI_KEY>
FOBXOZMHEKILEY-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.61616342239818

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

> <ALOGPS_LOGP>
4.65

> <JCHEM_LOGP>
4.101158186333333

> <ALOGPS_LOGS>
-5.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
65.6944

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.79e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035146
     RDKit          3D
Aristolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7482    2.4090    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    1.0417   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    0.5538    0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0870   -0.5317    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590   -1.4875   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883   -1.3324   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952   -2.3275    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -2.1424    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3300   -0.6960    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.0226   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    0.3929    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.6337    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.0418    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -0.0011   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -0.0634   -2.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    3.2188   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    2.5959    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    2.6470   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830    1.1849   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.3216    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8289    1.4292    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066   -0.0815   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5492   -1.0634    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -1.2949   -1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -2.5224   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -3.2769    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -2.7473    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606   -2.3567   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.5106    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6027   -0.5111   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.6471    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    2.5420    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    1.5900    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757   -0.4100   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230    0.9123    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -0.7595    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077    0.7241   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    0.2637   -2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -1.0555   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 14  2  1  0
 14  6  1  0
 11  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  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       1.224   5.906   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.088   3.253   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.681   5.147   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.142   4.670   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.530   2.903   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.918   4.316   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.612   1.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.836   0.607   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.366   0.784   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.612   4.493   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.918   1.844   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.977   2.197   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.060   3.433   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.590   3.610   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.530   3.257   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   10                                                       
CONECT    7    5   11                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    1    6   15                                                  
CONECT   11    7    8   15                                                  
CONECT   12    9   13   14                                                  
CONECT   13   12   14   15                                                  
CONECT   14    2    3   12   13                                             
CONECT   15    4   10   11   13                                             
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0035146
HETATM    1  C1  UNL     1      -0.748   2.409   0.020  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.257   1.042  -0.224  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.157   0.554   0.923  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.087  -0.532   0.405  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.359  -1.488  -0.538  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.888  -1.332  -0.307  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.195  -2.327   0.209  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.293  -2.142   0.436  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.330  -0.696   0.861  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.099   0.023  -0.513  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.113   0.393   0.418  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.098   1.634   1.321  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.583   0.042   0.110  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.322  -0.001  -0.708  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.597  -0.063  -2.255  1.00  0.00           C  
HETATM   16  H1  UNL     1      -1.473   3.219  -0.319  1.00  0.00           H  
HETATM   17  H2  UNL     1      -0.682   2.596   1.102  1.00  0.00           H  
HETATM   18  H3  UNL     1       0.160   2.647  -0.563  1.00  0.00           H  
HETATM   19  H4  UNL     1      -2.083   1.185  -1.002  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.640   0.322   1.837  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.829   1.429   1.140  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.907  -0.081  -0.193  1.00  0.00           H  
HETATM   23  H8  UNL     1      -3.549  -1.063   1.239  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.590  -1.295  -1.602  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.677  -2.522  -0.300  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.650  -3.277   0.478  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.619  -2.747   1.312  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.861  -2.357  -0.467  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.590  -0.511   1.661  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.603  -0.511  -1.406  1.00  0.00           H  
HETATM   31  H16 UNL     1       3.007   1.647   1.973  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.171   2.542   0.709  1.00  0.00           H  
HETATM   33  H18 UNL     1       1.255   1.590   2.021  1.00  0.00           H  
HETATM   34  H19 UNL     1       3.576  -0.410  -0.902  1.00  0.00           H  
HETATM   35  H20 UNL     1       4.223   0.912   0.081  1.00  0.00           H  
HETATM   36  H21 UNL     1       3.937  -0.760   0.798  1.00  0.00           H  
HETATM   37  H22 UNL     1       0.108   0.724  -2.651  1.00  0.00           H  
HETATM   38  H23 UNL     1      -1.615   0.264  -2.476  1.00  0.00           H  
HETATM   39  H24 UNL     1      -0.320  -1.055  -2.627  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3   14   19
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    7   14
CONECT    7    8   26
CONECT    8    9   27   28
CONECT    9   10   11   29
CONECT   10   11   14   30
CONECT   11   12   13
CONECT   12   31   32   33
CONECT   13   34   35   36
CONECT   14   15
CONECT   15   37   38   39
END

HMDB0035146
     RDKit          3D
Aristolene
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.7482    2.4090    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570    1.0417   -0.2244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1573    0.5538    0.9227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0870   -0.5317    0.4052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3590   -1.4875   -0.5382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8883   -1.3324   -0.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1952   -2.3275    0.2086 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2932   -2.1424    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3300   -0.6960    0.8613 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0987    0.0226   -0.5129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1133    0.3929    0.4177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0981    1.6337    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5826    0.0418    0.1104 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3219   -0.0011   -0.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5967   -0.0634   -2.2547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4730    3.2188   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6817    2.5959    1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    2.6470   -0.5633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0830    1.1849   -1.0015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6399    0.3216    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8289    1.4292    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066   -0.0815   -0.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5492   -1.0634    1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5896   -1.2949   -1.6022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6773   -2.5224   -0.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6498   -3.2769    0.4777 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6186   -2.7473    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8606   -2.3567   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -0.5106    1.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6027   -0.5111   -1.4064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0066    1.6471    1.9730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1707    2.5420    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2548    1.5900    2.0214 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757   -0.4100   -0.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230    0.9123    0.0805 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9372   -0.7595    0.7979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1077    0.7241   -2.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6148    0.2637   -2.4758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3196   -1.0555   -2.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  1  0
 14 15  1  0
 14  2  1  0
 14  6  1  0
 11  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-9-Aristolene	HMDB
(-)-Aristolene	HMDB
Aristol-9-ene	HMDB
Aristolen	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.3511

Monoisotopic Molecular Weight

204.187800768

IUPAC Name

1,1,7,7a-tetramethyl-1H,1aH,2H,4H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene

Traditional Name

1,1,7,7a-tetramethyl-1aH,2H,4H,5H,6H,7H,7bH-cyclopropa[a]naphthalene

CAS Registry Number

6831-16-9

SMILES

CC1CCCC2=CCC3C(C3(C)C)C12C

InChI Identifier

InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h8,10,12-13H,5-7,9H2,1-4H3

InChI Key

FOBXOZMHEKILEY-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6,C11 cyclization of the bicyclic eremophilane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Aristolane sesquiterpenoids

Alternative Parents

Substituents

Aristolane sesquiterpenoid
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035146)

Source

Endogenous

Endogenous (HMDB: HMDB0035146)

Plant

Plant (HMDB: HMDB0035146)

Animal

Animal (HMDB: HMDB0035146)

Exogenous

Food

Food (HMDB: HMDB0035146)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0035146)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035146)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035146)

Lipid metabolism pathway (HMDB: HMDB0035146)

Cellular process

Cell signaling (HMDB: HMDB0035146)

Biochemical process

Lipid transport (HMDB: HMDB0035146)

Role

Biological role

Energy source (HMDB: HMDB0035146)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035146)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	259.90 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.077 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.336 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0018 g/L	ALOGPS
logP	4.65	ALOGPS
logP	4.1	ChemAxon
logS	-5.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.69 m³·mol⁻¹	ChemAxon
Polarizability	25.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.824	31661259
DarkChem	[M-H]-	145.021	31661259
DeepCCS	[M-2H]-	186.023	30932474
DeepCCS	[M+Na]+	161.691	30932474
AllCCS	[M+H]+	147.3	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	158.4	32859911
AllCCS	[M+Na-2H]-	158.8	32859911
AllCCS	[M+HCOO]-	159.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aristolene	CC1CCCC2=CCC3C(C3(C)C)C12C	1614.6	Standard polar	33892256
Aristolene	CC1CCCC2=CCC3C(C3(C)C)C12C	1450.6	Standard non polar	33892256
Aristolene	CC1CCCC2=CCC3C(C3(C)C)C12C	1433.1	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 - Aristolene GC-MS (Non-derivatized) - 70eV, Positive	splash10-03g0-1900000000-f2172e810822d9aeeda7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aristolene 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 - Aristolene 10V, Positive-QTOF	splash10-0a4i-1290000000-a9fb95049f7ba8060e3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 20V, Positive-QTOF	splash10-0a4i-5940000000-5eadcb32b4e275b10473	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 40V, Positive-QTOF	splash10-01p6-8900000000-ef2e4e6debf38e32870a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 10V, Negative-QTOF	splash10-0udi-0090000000-aa082e67b2b9621ab56c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 20V, Negative-QTOF	splash10-0udi-0190000000-3060187c6c45a6bcdec5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 40V, Negative-QTOF	splash10-0fe0-1910000000-1688fb96d0aa53a2b773	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 40V, Negative-QTOF	splash10-0udi-0090000000-9102472d2cbae153f4fa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 10V, Positive-QTOF	splash10-0a4i-0490000000-befd697975c86820595e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 20V, Positive-QTOF	splash10-0bt9-4960000000-82068e9f58a8c9c6861a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aristolene 40V, Positive-QTOF	splash10-0006-9100000000-609137d5822017adf86d	2021-09-23	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

FDB013783

KNApSAcK ID

C00017471

Chemspider ID

462023

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

530421

PDB ID

Not Available

ChEBI ID

167397

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1561421

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 Aristolene (HMDB0035146)

MOL for HMDB0035146 (Aristolene)

3D MOL for HMDB0035146 (Aristolene)

3D SDF for HMDB0035146 (Aristolene)

3D-SDF for HMDB0035146 (Aristolene)

PDB for HMDB0035146 (Aristolene)

3D PDB for HMDB0035146 (Aristolene)

SMILES for HMDB0035146 (Aristolene)

INCHI for HMDB0035146 (Aristolene)

Structure for HMDB0035146 (Aristolene)

3D Structure for HMDB0035146 (Aristolene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra