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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:06:38 UTC

Update Date

2022-03-07 02:57:00 UTC

HMDB ID

HMDB0041425

Secondary Accession Numbers

HMDB41425

Metabolite Identification

Common Name

Isoleptospermone

Description

Isoleptospermone belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on Isoleptospermone.

Structure

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

HMDB0041425
     RDKit          3D
Isoleptospermone
 41 41  0  0  0  0  0  0  0  0999 V2000
    4.8229    0.0496    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802    0.5785   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    0.1535    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -1.3448   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.7379   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    1.4317   -1.8385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.6031   -0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -0.7402   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.4890   -1.8572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -1.2082   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838   -1.9670    0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -2.2173   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.0670    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -0.2388    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2593    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3230   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    1.7356    1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    1.1446    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.4535    1.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2053   -0.9551    0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.0431    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.7318    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    1.6768   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9696    0.1939   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214    0.4639    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -1.7210    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -1.7520    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -1.7520   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    1.2561   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043   -2.0687    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360   -1.3954    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -2.9722    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9319   -3.1299   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665   -2.4668   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.8185   -2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581    1.9427   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    2.8628   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    3.0928   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    1.6270    1.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080    1.1350    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.8074    1.8797 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061312402D          

 19 19  0  0  0  0            999 V2000
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822   -0.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.1433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  2  1  0  0  0  0
  8  7  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  0  0  0  0
 15  6  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  2  0  0  0  0
 17 11  2  0  0  0  0
 18 12  2  0  0  0  0
 19 13  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041425

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O4/c1-7-8(2)10(16)9-11(17)14(3,4)13(19)15(5,6)12(9)18/h8-9H,7H2,1-6H3

> <INCHI_KEY>
ZDZMTTISWJCOAE-UHFFFAOYSA-N

> <FORMULA>
C15H22O4

> <MOLECULAR_WEIGHT>
266.3328

> <EXACT_MASS>
266.151809192

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.36763421228511

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,4,4-tetramethyl-6-(2-methylbutanoyl)cyclohexane-1,3,5-trione

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
4.615958257

> <ALOGPS_LOGS>
-3.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.48195367617499

> <JCHEM_PKA_STRONGEST_BASIC>
-7.281643372265583

> <JCHEM_POLAR_SURFACE_AREA>
68.28

> <JCHEM_REFRACTIVITY>
71.48179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,4,4-tetramethyl-6-(2-methylbutanoyl)cyclohexane-1,3,5-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041425
     RDKit          3D
Isoleptospermone
 41 41  0  0  0  0  0  0  0  0999 V2000
    4.8229    0.0496    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802    0.5785   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    0.1535    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -1.3448   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.7379   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    1.4317   -1.8385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.6031   -0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -0.7402   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.4890   -1.8572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -1.2082   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838   -1.9670    0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -2.2173   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.0670    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -0.2388    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2593    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3230   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    1.7356    1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    1.1446    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.4535    1.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2053   -0.9551    0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.0431    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.7318    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    1.6768   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9696    0.1939   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214    0.4639    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -1.7210    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -1.7520    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -1.7520   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    1.2561   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043   -2.0687    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360   -1.3954    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -2.9722    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9319   -3.1299   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665   -2.4668   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.8185   -2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581    1.9427   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    2.8628   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    3.0928   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    1.6270    1.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080    1.1350    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.8074    1.8797 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.527  -1.447   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.517   0.267   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6   15                                                            
CONECT    7    1    8                                                       
CONECT    8    2    7   10                                                  
CONECT    9   10   11   12                                                  
CONECT   10    8    9   16                                                  
CONECT   11    9   14   17                                                  
CONECT   12    9   15   18                                                  
CONECT   13   14   15   19                                                  
CONECT   14    3    4   11   13                                             
CONECT   15    5    6   12   13                                             
CONECT   16   10                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0041425
HETATM    1  C1  UNL     1       4.823   0.050   0.552  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.780   0.578  -0.369  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.375   0.153   0.008  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.360  -1.345  -0.038  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.400   0.738  -0.908  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.851   1.432  -1.839  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.071   0.603  -0.863  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.608  -0.740  -1.056  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.089  -1.489  -1.857  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.781  -1.208  -0.293  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.384  -1.967   0.956  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.562  -2.217  -1.149  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.694  -0.067   0.065  1.00  0.00           C  
HETATM   14  O3  UNL     1      -3.879  -0.239   0.039  1.00  0.00           O  
HETATM   15  C12 UNL     1      -2.127   1.259   0.446  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.449   2.323  -0.579  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.628   1.736   1.790  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.611   1.145   0.441  1.00  0.00           C  
HETATM   19  O4  UNL     1       0.076   1.453   1.376  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.205  -0.955   0.287  1.00  0.00           H  
HETATM   21  H2  UNL     1       4.506   0.043   1.610  1.00  0.00           H  
HETATM   22  H3  UNL     1       5.709   0.732   0.495  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.881   1.677  -0.433  1.00  0.00           H  
HETATM   24  H5  UNL     1       3.970   0.194  -1.410  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.221   0.464   1.073  1.00  0.00           H  
HETATM   26  H7  UNL     1       1.430  -1.721   0.382  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.262  -1.752   0.520  1.00  0.00           H  
HETATM   28  H9  UNL     1       2.487  -1.752  -1.057  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.537   1.256  -1.636  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.304  -2.069   1.570  1.00  0.00           H  
HETATM   31  H12 UNL     1      -0.636  -1.395   1.557  1.00  0.00           H  
HETATM   32  H13 UNL     1      -1.020  -2.972   0.752  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.932  -3.130  -1.163  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.467  -2.467  -0.545  1.00  0.00           H  
HETATM   35  H16 UNL     1      -2.799  -1.818  -2.137  1.00  0.00           H  
HETATM   36  H17 UNL     1      -2.458   1.943  -1.610  1.00  0.00           H  
HETATM   37  H18 UNL     1      -3.387   2.863  -0.340  1.00  0.00           H  
HETATM   38  H19 UNL     1      -1.636   3.093  -0.541  1.00  0.00           H  
HETATM   39  H20 UNL     1      -3.711   1.627   1.807  1.00  0.00           H  
HETATM   40  H21 UNL     1      -2.208   1.135   2.627  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.361   2.807   1.880  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3   23   24
CONECT    3    4    5   25
CONECT    4   26   27   28
CONECT    5    6    6    7
CONECT    7    8   18   29
CONECT    8    9    9   10
CONECT   10   11   12   13
CONECT   11   30   31   32
CONECT   12   33   34   35
CONECT   13   14   14   15
CONECT   15   16   17   18
CONECT   16   36   37   38
CONECT   17   39   40   41
CONECT   18   19   19
END

HMDB0041425
     RDKit          3D
Isoleptospermone
 41 41  0  0  0  0  0  0  0  0999 V2000
    4.8229    0.0496    0.5523 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7802    0.5785   -0.3693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3755    0.1535    0.0082 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3603   -1.3448   -0.0376 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3998    0.7379   -0.9081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514    1.4317   -1.8385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0706    0.6031   -0.8627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6085   -0.7402   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0890   -1.4890   -1.8572 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7807   -1.2082   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3838   -1.9670    0.9561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5623   -2.2173   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6936   -0.0670    0.0649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8793   -0.2388    0.0393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1272    1.2593    0.4461 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4489    2.3230   -0.5789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6284    1.7356    1.7897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6113    1.1446    0.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0761    1.4535    1.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2053   -0.9551    0.2865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5060    0.0431    1.6098 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7086    0.7318    0.4953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8807    1.6768   -0.4328 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9696    0.1939   -1.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2214    0.4639    1.0730 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4301   -1.7210    0.3821 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2622   -1.7520    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -1.7520   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368    1.2561   -1.6359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3043   -2.0687    1.5701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6360   -1.3954    1.5573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0195   -2.9722    0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9319   -3.1299   -1.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4665   -2.4668   -0.5446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7987   -1.8185   -2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4581    1.9427   -1.6096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3867    2.8628   -0.3400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    3.0928   -0.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7111    1.6270    1.8067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2080    1.1350    2.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3605    2.8074    1.8797 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 18  1  0
 18 19  2  0
 18  7  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  2 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  4 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,2,4,4-Tetramethyl-6-(2-methyl-1-oxobutyl)-1,3,5-cyclohexanetrione	HMDB

Chemical Formula

C₁₅H₂₂O₄

Average Molecular Weight

266.3328

Monoisotopic Molecular Weight

266.151809192

IUPAC Name

2,2,4,4-tetramethyl-6-(2-methylbutanoyl)cyclohexane-1,3,5-trione

Traditional Name

2,2,4,4-tetramethyl-6-(2-methylbutanoyl)cyclohexane-1,3,5-trione

CAS Registry Number

7375-66-8

SMILES

CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O

InChI Identifier

InChI=1S/C15H22O4/c1-7-8(2)10(16)9-11(17)14(3,4)13(19)15(5,6)12(9)18/h8-9H,7H2,1-6H3

InChI Key

ZDZMTTISWJCOAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Monocyclic monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
1,3-diketone
1,3-dicarbonyl compound
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0041425)
Cell membrane (HMDB: HMDB0041425)

Cellular substructure

Extracellular (HMDB: HMDB0041425)
Membrane (HMDB: HMDB0041425)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041425)

Source

Endogenous

Endogenous (HMDB: HMDB0041425)

Plant

Plant (HMDB: HMDB0041425)

Animal

Animal (HMDB: HMDB0041425)

Exogenous

Food

Food (HMDB: HMDB0041425)

Tea

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041425)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041425)

Cellular process

Cell signaling (HMDB: HMDB0041425)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041425)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041425)

Nutrient

Nutrient (HMDB: HMDB0041425)

Industrial application

Pharmaceutical industry

Antimicrobial agent

Antimicrobial agent (HMDB: HMDB0041425)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041425)

Emulsifier (HMDB: HMDB0041425)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	2.8	ALOGPS
logP	4.62	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	3.48	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	68.28 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.48 m³·mol⁻¹	ChemAxon
Polarizability	28.37 Å³	ChemAxon
Number of Rings	1	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]+	164.328	31661259
DarkChem	[M-H]-	163.923	31661259
DeepCCS	[M+H]+	176.686	30932474
DeepCCS	[M-H]-	174.328	30932474
DeepCCS	[M-2H]-	207.214	30932474
DeepCCS	[M+Na]+	182.779	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.7	32859911
AllCCS	[M+NH4]+	162.1	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	168.3	32859911
AllCCS	[M+Na-2H]-	168.9	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoleptospermone	CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	2104.7	Standard polar	33892256
Isoleptospermone	CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1645.3	Standard non polar	33892256
Isoleptospermone	CCC(C)C(=O)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1623.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoleptospermone,1TMS,isomer #1	CCC(C)C(O[Si](C)(C)C)=C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1845.3	Semi standard non polar	33892256
Isoleptospermone,1TMS,isomer #1	CCC(C)C(O[Si](C)(C)C)=C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1893.6	Standard non polar	33892256
Isoleptospermone,1TMS,isomer #2	CCC(C)=C(O[Si](C)(C)C)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1935.6	Semi standard non polar	33892256
Isoleptospermone,1TMS,isomer #2	CCC(C)=C(O[Si](C)(C)C)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	1994.5	Standard non polar	33892256
Isoleptospermone,1TMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	1817.0	Semi standard non polar	33892256
Isoleptospermone,1TMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	1837.3	Standard non polar	33892256
Isoleptospermone,2TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	1962.4	Semi standard non polar	33892256
Isoleptospermone,2TMS,isomer #1	CCC(C)=C(O[Si](C)(C)C)C1=C(O[Si](C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	1984.2	Standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #1	CCC(C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	2080.4	Semi standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #1	CCC(C)C(O[Si](C)(C)C(C)(C)C)=C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	2137.5	Standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #2	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	2168.3	Semi standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #2	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1C(=O)C(C)(C)C(=O)C(C)(C)C1=O	2266.3	Standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	2056.7	Semi standard non polar	33892256
Isoleptospermone,1TBDMS,isomer #3	CCC(C)C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	2062.9	Standard non polar	33892256
Isoleptospermone,2TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	2401.7	Semi standard non polar	33892256
Isoleptospermone,2TBDMS,isomer #1	CCC(C)=C(O[Si](C)(C)C(C)(C)C)C1=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(=O)C(C)(C)C1=O	2426.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoleptospermone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4r-9530000000-4e202a36d8ef0eb525fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoleptospermone 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 - Isoleptospermone 10V, Negative-QTOF	splash10-014i-0190000000-d9f92f15476d8d2a3731	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 20V, Negative-QTOF	splash10-001i-2940000000-01dab886678c7f3d41fb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 40V, Negative-QTOF	splash10-001i-8910000000-ff809c4a180f7382bd4c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 10V, Negative-QTOF	splash10-014i-0090000000-c6cc318d73093d112373	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 20V, Negative-QTOF	splash10-014i-0290000000-f69791d677eec21e2746	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 40V, Negative-QTOF	splash10-014i-9420000000-2a7a02ef620560b6445d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 10V, Positive-QTOF	splash10-014i-0090000000-3056348940cbfefe8156	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 20V, Positive-QTOF	splash10-0ap0-3190000000-b482f339e9a81ba962f5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 40V, Positive-QTOF	splash10-0a4i-9200000000-4ebb3b89c79d554f65f7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 10V, Positive-QTOF	splash10-014j-0090000000-24825e227ccdc853ed18	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 20V, Positive-QTOF	splash10-066s-4690000000-4985514c2ea428d30e68	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoleptospermone 40V, Positive-QTOF	splash10-00xu-8940000000-a5a4175d9b589653a3f5	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

FDB021371

KNApSAcK ID

C00035664

Chemspider ID

35015182

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59518515

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

Mustafa K, Perry NB, Weavers RT: 2-Hydroxyflavanones from Leptospermum polygalifolium subsp. polygalifolium Equilibrating sets of hemiacetal isomers. Phytochemistry. 2003 Dec;64(7):1285-93. [PubMed:14599527 ]
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 Isoleptospermone (HMDB0041425)

MOL for HMDB0041425 (Isoleptospermone)

3D MOL for HMDB0041425 (Isoleptospermone)

3D SDF for HMDB0041425 (Isoleptospermone)

3D-SDF for HMDB0041425 (Isoleptospermone)

PDB for HMDB0041425 (Isoleptospermone)

3D PDB for HMDB0041425 (Isoleptospermone)

SMILES for HMDB0041425 (Isoleptospermone)

INCHI for HMDB0041425 (Isoleptospermone)

Structure for HMDB0041425 (Isoleptospermone)

3D Structure for HMDB0041425 (Isoleptospermone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra