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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 16:47:32 UTC

Update Date

2021-09-23 16:47:32 UTC

HMDB ID

HMDB0302310

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydrofukinone

Description

Dehydrofukinone is a member of the class of compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids 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. Dehydrofukinone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Dehydrofukinone can be found in burdock, which makes dehydrofukinone a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302310
     RDKit          3D
Dehydrofukinone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.9843   -0.2676    0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.2715   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -1.1089   -1.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914    0.4417    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.4863   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170    0.1106   -0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5303   -1.3638    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    0.9482    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.4750    1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.2543    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    1.7197    1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034    1.2344    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.0999    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -0.0538   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    0.3567   -0.9928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7400   -0.4272   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5253    0.7044    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6781   -1.1110    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -0.4194    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -1.3508   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599   -0.5886   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677   -2.0743   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.5368   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.2037   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7839   -0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.9513   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -1.4888    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915    2.0648    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    2.1353    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    1.4285    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309    0.2571    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -0.8363    1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -1.0873   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162    0.6079   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    1.4297   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888   -1.5048   -2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.1622   -2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -0.2360   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  4  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

  Mrv0541 02241212582D          

 16 17  0  0  0  0            999 V2000
   -2.0920   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8064   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -2.6223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3775   -2.2098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3775   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -0.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6630   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0514   -1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -0.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4804   -2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7659   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3775   -3.0348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0920   -3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  7  6  2  0  0  0  0
  6  5  1  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  9 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  1  0  0  0
  4 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302310

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1CCCC2=CC(=O)C(C[C@]12C)=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11H,5-7,9H2,1-4H3/t11-,15+/m0/s1

> <INCHI_KEY>
DZOKWSREAZGFFC-XHDPSFHLSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.129328312798208

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.99

> <JCHEM_LOGP>
4.110179681666667

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.300940482888244

> <JCHEM_PKA_STRONGEST_BASIC>
-4.330450878242347

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.9282

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-5,6,7,8-tetrahydro-4H-naphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302310
     RDKit          3D
Dehydrofukinone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.9843   -0.2676    0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.2715   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -1.1089   -1.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914    0.4417    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.4863   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170    0.1106   -0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5303   -1.3638    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    0.9482    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.4750    1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.2543    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    1.7197    1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034    1.2344    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.0999    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -0.0538   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    0.3567   -0.9928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7400   -0.4272   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5253    0.7044    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6781   -1.1110    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -0.4194    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -1.3508   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599   -0.5886   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677   -2.0743   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.5368   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.2037   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7839   -0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.9513   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -1.4888    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915    2.0648    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    2.1353    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    1.4285    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309    0.2571    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -0.8363    1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -1.0873   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162    0.6079   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    1.4297   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888   -1.5048   -2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.1622   -2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -0.2360   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  4  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -3.905  -1.815   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.239  -2.585   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.239  -4.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.905  -4.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.571  -4.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.571  -2.585   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.238  -1.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.238  -4.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.096  -4.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.096  -2.585   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.430  -1.815   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.430  -4.895   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.763  -4.125   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.430  -6.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.571  -5.665   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.905  -6.435   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6    8   15                                             
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   12                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10                                                            
CONECT   12    9   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5                                                            
CONECT   16    4                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0302310
HETATM    1  C1  UNL     1       3.984  -0.268   0.903  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.873  -0.272  -0.103  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.059  -1.109  -1.315  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.791   0.442   0.093  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.635   0.486  -0.873  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.617   0.111  -0.127  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.530  -1.364   0.219  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.734   0.948   1.089  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.286   1.475   1.751  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.661   1.254   1.294  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.656   1.720   1.878  1.00  0.00           O  
HETATM   12  C11 UNL     1      -2.103   1.234   1.589  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.008   0.100   1.206  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.104  -0.054  -0.286  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.835   0.357  -0.993  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.740  -0.427  -2.277  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.525   0.704   0.912  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.678  -1.111   0.726  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.591  -0.419   1.940  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.153  -1.351  -1.458  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.760  -0.589  -2.251  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.568  -2.074  -1.157  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.551   1.537  -1.207  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.835  -0.204  -1.720  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.343  -1.784  -0.319  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.398  -1.951  -0.100  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.306  -1.489   1.298  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.092   2.065   2.625  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.463   2.135   1.017  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.122   1.429   2.672  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.031   0.257   1.646  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.582  -0.836   1.619  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.387  -1.087  -0.590  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.916   0.608  -0.653  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.864   1.430  -1.261  1.00  0.00           H  
HETATM   36  H20 UNL     1      -1.789  -1.505  -2.032  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.837  -0.162  -2.875  1.00  0.00           H  
HETATM   38  H22 UNL     1      -2.675  -0.236  -2.882  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   10
CONECT    5    6   23   24
CONECT    6    7    8   15
CONECT    7   25   26   27
CONECT    8    9    9   12
CONECT    9   10   28
CONECT   10   11   11
CONECT   12   13   29   30
CONECT   13   14   31   32
CONECT   14   15   33   34
CONECT   15   16   35
CONECT   16   36   37   38
END

HMDB0302310
     RDKit          3D
Dehydrofukinone
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.9843   -0.2676    0.9027 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8732   -0.2715   -0.1033 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0590   -1.1089   -1.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7914    0.4417    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6355    0.4863   -0.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6170    0.1106   -0.1269 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5303   -1.3638    0.2188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7338    0.9482    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    1.4750    1.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611    1.2543    1.2939 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6555    1.7197    1.8778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1034    1.2344    1.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0084    0.0999    1.2064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1044   -0.0538   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8353    0.3567   -0.9928 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7400   -0.4272   -2.2775 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5253    0.7044    0.9124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6781   -1.1110    0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5914   -0.4194    1.9397 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1529   -1.3508   -1.4578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599   -0.5886   -2.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677   -2.0743   -1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5513    1.5368   -1.2074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8355   -0.2037   -1.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3432   -1.7839   -0.3186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3985   -1.9513   -0.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3059   -1.4888    1.2979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0915    2.0648    2.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4633    2.1353    1.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1219    1.4285    2.6723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0309    0.2571    1.6462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5817   -0.8363    1.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3868   -1.0873   -0.5898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9162    0.6079   -0.6525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8640    1.4297   -1.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7888   -1.5048   -2.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8374   -0.1622   -2.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6746   -0.2360   -2.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 10  4  1  0
 15  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  5 23  1  0
  5 24  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  9 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  6
 16 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

Traditional Name

(4aR,5S)-4a,5-dimethyl-3-(propan-2-ylidene)-5,6,7,8-tetrahydro-4H-naphthalen-2-one

CAS Registry Number

Not Available

SMILES

C[C@H]1CCCC2=CC(=O)C(C[C@]12C)=C(C)C

InChI Identifier

InChI=1S/C15H22O/c1-10(2)13-9-15(4)11(3)6-5-7-12(15)8-14(13)16/h8,11H,5-7,9H2,1-4H3/t11-,15+/m0/s1

InChI Key

DZOKWSREAZGFFC-XHDPSFHLSA-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
Quinomethane
O-quinomethane
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302310)

Food

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

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
logP	3.99	ALOGPS
logP	4.11	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	19.3	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.93 m³·mol⁻¹	ChemAxon
Polarizability	26.13 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
AllCCS	[M+H]+	150.284	32859911
AllCCS	[M+H-H2O]+	146.384	32859911
AllCCS	[M+Na]+	154.957	32859911
AllCCS	[M+NH4]+	153.912	32859911
AllCCS	[M-H]-	159.684	32859911
AllCCS	[M+Na-2H]-	160.115	32859911
AllCCS	[M+HCOO]-	160.695	32859911
DeepCCS	[M-2H]-	188.481	30932474
DeepCCS	[M+Na]+	163.634	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 10V, Positive-QTOF	splash10-014i-0390000000-f36fc5c0a5191213f606	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 20V, Positive-QTOF	splash10-016r-3930000000-53e406c6856d2f5bcb1f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 40V, Positive-QTOF	splash10-0gbc-9500000000-fba08c301406f6bad58d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 10V, Negative-QTOF	splash10-014i-0090000000-5e842cdb5cbea37ebc2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 20V, Negative-QTOF	splash10-014i-0290000000-f199693038208b9697ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 40V, Negative-QTOF	splash10-0ug0-1930000000-be441e88a8971544b561	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 10V, Positive-QTOF	splash10-014i-0290000000-b54e464131fe59c228d0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 20V, Positive-QTOF	splash10-014l-4910000000-2aebfff5738f8ace6709	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 40V, Positive-QTOF	splash10-00kf-9710000000-734f4ecba8cdb64477fe	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 20V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrofukinone 40V, Negative-QTOF	splash10-014i-0930000000-5cc2ec2ece32cc8f36d0	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB004100

KNApSAcK ID

C00017004

Chemspider ID

154205

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177072

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

Not Available

Showing metabocard for Dehydrofukinone (HMDB0302310)

MOL for HMDB0302310 (Dehydrofukinone)

3D MOL for HMDB0302310 (Dehydrofukinone)

3D SDF for HMDB0302310 (Dehydrofukinone)

3D-SDF for HMDB0302310 (Dehydrofukinone)

PDB for HMDB0302310 (Dehydrofukinone)

3D PDB for HMDB0302310 (Dehydrofukinone)

SMILES for HMDB0302310 (Dehydrofukinone)

INCHI for HMDB0302310 (Dehydrofukinone)

Structure for HMDB0302310 (Dehydrofukinone)

3D Structure for HMDB0302310 (Dehydrofukinone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra