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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:25:41 UTC

Update Date

2022-03-07 02:55:38 UTC

HMDB ID

HMDB0038144

Secondary Accession Numbers

HMDB38144

Metabolite Identification

Common Name

Petasitolone

Description

Petasitolone belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a small amount of articles have been published on Petasitolone.

Structure

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

HMDB0038144
     RDKit          3D
Petasitolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    1.2728   -2.1583   -1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -1.0909   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.0899   -1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172    0.8499   -0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    1.6229    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.8014    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    1.7379    1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    1.1151    1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    1.3823    2.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    0.1569    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145    0.0432   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605    1.3423   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -0.2534    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.0203   -1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285   -0.5972   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.5034    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9108   -1.5338    1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -2.7687   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.7431   -2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -2.8680   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -1.5991   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436    0.4763   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966   -0.6100   -2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401    0.2168    0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059    1.5639   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985    2.3511    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7406    2.2607   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    0.6458    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.5482    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876    2.2105    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0410    1.1531   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    2.0096   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    1.8701   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5535   -0.9538    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1297    0.6924    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769   -0.7486    1.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -1.8585   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -1.3068   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -1.4739    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440   -1.3102    2.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -2.5629    1.1185 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  1  0
 16  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 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
 14 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061310152D          

 17 18  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6993   -0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
    0.7145   -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
    2.8579    0.0000    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
    1.4289   -1.6500    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -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
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8743   -2.3645    0.0000 O   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
 10  1  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  8  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
 15  4  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038144

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2CC(=O)C(=CC12C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10-6-5-7-11-8-13(16)12(14(2,3)17)9-15(10,11)4/h9-11,17H,5-8H2,1-4H3

> <INCHI_KEY>
LYFRYUAWUBLCKH-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.52734951259501

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.36

> <JCHEM_LOGP>
2.884464616333333

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.802818008154738

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.525958633562247

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006143805212325

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.05019999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.63e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038144
     RDKit          3D
Petasitolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    1.2728   -2.1583   -1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -1.0909   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.0899   -1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172    0.8499   -0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    1.6229    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.8014    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    1.7379    1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    1.1151    1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    1.3823    2.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    0.1569    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145    0.0432   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605    1.3423   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -0.2534    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.0203   -1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285   -0.5972   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.5034    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9108   -1.5338    1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -2.7687   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.7431   -2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -2.8680   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -1.5991   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436    0.4763   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966   -0.6100   -2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401    0.2168    0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059    1.5639   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985    2.3511    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7406    2.2607   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    0.6458    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.5482    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876    2.2105    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0410    1.1531   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    2.0096   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    1.8701   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5535   -0.9538    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1297    0.6924    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769   -0.7486    1.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -1.8585   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -1.3068   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -1.4739    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440   -1.3102    2.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -2.5629    1.1185 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  1  0
 16  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 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
 14 37  1  0
 15 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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.772  -1.746   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.232  -4.414   0.000  0.00  0.00           O+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   11   13                                                       
CONECT    9   12   15                                                       
CONECT   10    1    6   15                                                  
CONECT   11    7    8   15                                                  
CONECT   12    9   13   14                                                  
CONECT   13    8   12   16                                                  
CONECT   14    2    3   12   17                                             
CONECT   15    4    9   10   11                                             
CONECT   16   13                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0038144
HETATM    1  C1  UNL     1       1.273  -2.158  -1.452  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.899  -1.091  -0.598  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.545  -0.090  -1.499  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.317   0.850  -0.557  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.279   1.623   0.168  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.299   0.801   0.957  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.160   1.738   1.281  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.173   1.115   1.267  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.060   1.382   2.117  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.436   0.157   0.208  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.814   0.043  -0.384  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.260   1.342  -1.000  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.740  -0.253   0.783  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.873  -1.020  -1.249  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.429  -0.597  -0.190  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.934  -0.503   0.396  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.911  -1.534   1.549  1.00  0.00           C  
HETATM   18  H1  UNL     1       2.130  -2.769  -1.865  1.00  0.00           H  
HETATM   19  H2  UNL     1       0.776  -1.743  -2.368  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.646  -2.868  -0.902  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.738  -1.599  -0.034  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.844   0.476  -2.121  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.297  -0.610  -2.106  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.940   0.217   0.089  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.906   1.564  -1.170  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.798   2.351   0.844  1.00  0.00           H  
HETATM   27  H10 UNL     1       1.741   2.261  -0.577  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.828   0.646   1.957  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.124   2.548   0.489  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.288   2.211   2.283  1.00  0.00           H  
HETATM   31  H14 UNL     1      -4.041   1.153  -1.750  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.699   2.010  -0.230  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.385   1.870  -1.413  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.553  -0.954   0.504  1.00  0.00           H  
HETATM   35  H18 UNL     1      -4.130   0.692   1.204  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.177  -0.749   1.601  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.874  -1.859  -0.689  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.663  -1.307  -0.991  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.831  -1.474   2.144  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.044  -1.310   2.188  1.00  0.00           H  
HETATM   41  H24 UNL     1       0.761  -2.563   1.118  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3   16   21
CONECT    3    4   22   23
CONECT    4    5   24   25
CONECT    5    6   26   27
CONECT    6    7   16   28
CONECT    7    8   29   30
CONECT    8    9    9   10
CONECT   10   11   15   15
CONECT   11   12   13   14
CONECT   12   31   32   33
CONECT   13   34   35   36
CONECT   14   37
CONECT   15   16   38
CONECT   16   17
CONECT   17   39   40   41
END

HMDB0038144
     RDKit          3D
Petasitolone
 41 42  0  0  0  0  0  0  0  0999 V2000
    1.2728   -2.1583   -1.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991   -1.0909   -0.5981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5451   -0.0899   -1.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3172    0.8499   -0.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2787    1.6229    0.1681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2991    0.8014    0.9572 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1602    1.7379    1.2812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1729    1.1151    1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    1.3823    2.1175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4358    0.1569    0.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8145    0.0432   -0.3839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2605    1.3423   -0.9997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7401   -0.2534    0.7826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8729   -1.0203   -1.2493 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4285   -0.5972   -0.1895 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9340   -0.5034    0.3965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9108   -1.5338    1.5487 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1295   -2.7687   -1.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7762   -1.7431   -2.3683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6462   -2.8680   -0.9020 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7376   -1.5991   -0.0343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8436    0.4763   -2.1213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2966   -0.6100   -2.1064 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9401    0.2168    0.0886 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9059    1.5639   -1.1696 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985    2.3511    0.8438 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7406    2.2607   -0.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8283    0.6458    1.9566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1238    2.5482    0.4887 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2876    2.2105    2.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0410    1.1531   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6989    2.0096   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3854    1.8701   -1.4133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5535   -0.9538    0.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1297    0.6924    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1769   -0.7486    1.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737   -1.8585   -0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -1.3068   -0.9910 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8312   -1.4739    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0440   -1.3102    2.1875 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610   -2.5629    1.1185 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  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 10 15  2  0
 15 16  1  0
 16 17  1  0
 16  2  1  0
 16  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  7 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
 14 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one

Traditional Name

3-(2-hydroxypropan-2-yl)-4a,5-dimethyl-1,5,6,7,8,8a-hexahydronaphthalen-2-one

CAS Registry Number

35124-22-2

SMILES

CC1CCCC2CC(=O)C(=CC12C)C(C)(C)O

InChI Identifier

InChI=1S/C15H24O2/c1-10-6-5-7-11-8-13(16)12(14(2,3)17)9-15(10,11)4/h9-11,17H,5-8H2,1-4H3

InChI Key

LYFRYUAWUBLCKH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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: HMDB0038144)

Source

Endogenous

Endogenous (HMDB: HMDB0038144)

Plant

Plant (HMDB: HMDB0038144)

Animal

Animal (HMDB: HMDB0038144)

Exogenous

Food

Food (HMDB: HMDB0038144)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Other vegetable

Giant butterbur (FooDB: FOOD00314)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Exogenous (HMDB: HMDB0038144)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038144)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038144)

Lipid metabolism pathway (HMDB: HMDB0038144)

Cellular process

Cell signaling (HMDB: HMDB0038144)

Biochemical process

Lipid transport (HMDB: HMDB0038144)

Role

Biological role

Energy source (HMDB: HMDB0038144)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038144)

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	116.5 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	0.086 g/L	ALOGPS
logP	3.36	ALOGPS
logP	2.88	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.53	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.05 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	2	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]+	155.388	31661259
DarkChem	[M-H]-	151.452	31661259
DeepCCS	[M-2H]-	193.766	30932474
DeepCCS	[M+Na]+	169.332	30932474
AllCCS	[M+H]+	155.2	32859911
AllCCS	[M+H-H2O]+	151.5	32859911
AllCCS	[M+NH4]+	158.6	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	164.0	32859911
AllCCS	[M+HCOO]-	164.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.46 minutes	32390414
Predicted by Siyang on May 30, 2022	14.7283 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.61 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2322.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	382.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	180.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	188.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	654.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	752.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1149.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	450.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1255.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	404.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	370.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	432.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Petasitolone	CC1CCCC2CC(=O)C(=CC12C)C(C)(C)O	2645.3	Standard polar	33892256
Petasitolone	CC1CCCC2CC(=O)C(=CC12C)C(C)(C)O	1696.5	Standard non polar	33892256
Petasitolone	CC1CCCC2CC(=O)C(=CC12C)C(C)(C)O	1811.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Petasitolone,1TMS,isomer #1	CC1CCCC2CC(=O)C(C(C)(C)O[Si](C)(C)C)=CC12C	1944.3	Semi standard non polar	33892256
Petasitolone,1TMS,isomer #2	CC1CCCC2C=C(O[Si](C)(C)C)C(C(C)(C)O)=CC12C	1908.8	Semi standard non polar	33892256
Petasitolone,2TMS,isomer #1	CC1CCCC2C=C(O[Si](C)(C)C)C(C(C)(C)O[Si](C)(C)C)=CC12C	1953.2	Semi standard non polar	33892256
Petasitolone,2TMS,isomer #1	CC1CCCC2C=C(O[Si](C)(C)C)C(C(C)(C)O[Si](C)(C)C)=CC12C	1922.3	Standard non polar	33892256
Petasitolone,1TBDMS,isomer #1	CC1CCCC2CC(=O)C(C(C)(C)O[Si](C)(C)C(C)(C)C)=CC12C	2211.8	Semi standard non polar	33892256
Petasitolone,1TBDMS,isomer #2	CC1CCCC2C=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)O)=CC12C	2148.0	Semi standard non polar	33892256
Petasitolone,2TBDMS,isomer #1	CC1CCCC2C=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)O[Si](C)(C)C(C)(C)C)=CC12C	2412.9	Semi standard non polar	33892256
Petasitolone,2TBDMS,isomer #1	CC1CCCC2C=C(O[Si](C)(C)C(C)(C)C)C(C(C)(C)O[Si](C)(C)C(C)(C)C)=CC12C	2346.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Petasitolone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-3960000000-5812ef1d8ab7f2f4d9f0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasitolone GC-MS (1 TMS) - 70eV, Positive	splash10-0006-6290000000-9d69c73da419ae124cb4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasitolone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Petasitolone 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 - Petasitolone 10V, Positive-QTOF	splash10-014r-0190000000-403914516d53f985065b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 20V, Positive-QTOF	splash10-00n0-2970000000-8b1736395884dc949671	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 40V, Positive-QTOF	splash10-0ldl-7910000000-8f2654a3c41498bf8f17	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 10V, Negative-QTOF	splash10-000i-0190000000-8f0f5e14687cc8f68725	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 20V, Negative-QTOF	splash10-002r-0690000000-d88ffc093e8cd29dde45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 40V, Negative-QTOF	splash10-01tc-3920000000-c1d5c1fbbb0493876344	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 20V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 40V, Negative-QTOF	splash10-001r-0490000000-e8e1957a9a4d04d719af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 10V, Positive-QTOF	splash10-014i-0290000000-40cd3ea4a87dd5e8e28e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 20V, Positive-QTOF	splash10-0a4i-2920000000-0731f43a140c40735881	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Petasitolone 40V, Positive-QTOF	splash10-0a4r-7910000000-5da4e2156a3771730acf	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017372

KNApSAcK ID

C00017018

Chemspider ID

35014519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75079051

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866021

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 Petasitolone (HMDB0038144)

MOL for HMDB0038144 (Petasitolone)

3D MOL for HMDB0038144 (Petasitolone)

3D SDF for HMDB0038144 (Petasitolone)

3D-SDF for HMDB0038144 (Petasitolone)

PDB for HMDB0038144 (Petasitolone)

3D PDB for HMDB0038144 (Petasitolone)

SMILES for HMDB0038144 (Petasitolone)

INCHI for HMDB0038144 (Petasitolone)

Structure for HMDB0038144 (Petasitolone)

3D Structure for HMDB0038144 (Petasitolone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra