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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:10:36 UTC

Update Date

2022-03-07 02:54:47 UTC

HMDB ID

HMDB0036110

Secondary Accession Numbers

HMDB36110

Metabolite Identification

Common Name

(S)-Bilobanone

Description

(S)-Bilobanone belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond (S)-Bilobanone has been detected, but not quantified in, fats and oils and ginkgo nuts (Ginkgo biloba). This could make (S)-bilobanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (S)-Bilobanone.

Structure

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

HMDB0036110
     RDKit          3D
(S)-Bilobanone
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.6134    1.5459   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.2697   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.0381    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -1.3119    1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462   -1.6249    0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892   -0.8301    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514    0.5297   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431    0.8275   -0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.2450    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -0.4127    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8555    0.9128    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3407    0.6297    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002    1.5954   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -1.3211    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -1.4826   -1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059   -0.6713   -1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6460   -0.7756   -2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    2.2034    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2615    2.0918   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    1.3423   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    0.6701    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -1.2269    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.1847    1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4718   -2.7141    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    1.2716   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.9296    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.0161   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330    1.5887    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6474    0.1333   -0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -0.0795    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    1.5429    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323    0.8816   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866    2.2349   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3258   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -2.3793    0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -2.4308   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -0.9228   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  9 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 14  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 05061308532D          

 17 18  0  0  0  0            999 V2000
    3.7980   -3.4197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4926   -2.8385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    3.2384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0367    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6486   -1.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4186   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    1.1759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0837   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3130   -2.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    2.4134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512    0.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7512   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1637   -1.3312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4656    2.0009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1801    2.4134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387   -1.3312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  3  1  0  0  0  0
 11  4  2  0  0  0  0
 12  5  1  0  0  0  0
 12  8  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
 16 15  2  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036110

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)CC1=CC(=CO1)C1CC=C(C)C(=O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-10(2)6-14-7-13(9-17-14)12-5-4-11(3)15(16)8-12/h4,7,9-10,12H,5-6,8H2,1-3H3

> <INCHI_KEY>
ORQIZUYAGXZVPI-UHFFFAOYSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.416225930413663

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-[5-(2-methylpropyl)furan-3-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
3.8963083123333324

> <ALOGPS_LOGS>
-3.91

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.86692613307844

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7208563414309035

> <JCHEM_POLAR_SURFACE_AREA>
30.21

> <JCHEM_REFRACTIVITY>
69.6781

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-[5-(2-methylpropyl)furan-3-yl]cyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036110
     RDKit          3D
(S)-Bilobanone
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.6134    1.5459   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.2697   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.0381    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -1.3119    1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462   -1.6249    0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892   -0.8301    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514    0.5297   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431    0.8275   -0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.2450    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -0.4127    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8555    0.9128    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3407    0.6297    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002    1.5954   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -1.3211    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -1.4826   -1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059   -0.6713   -1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6460   -0.7756   -2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    2.2034    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2615    2.0918   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    1.3423   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    0.6701    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -1.2269    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.1847    1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4718   -2.7141    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    1.2716   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.9296    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.0161   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330    1.5887    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6474    0.1333   -0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -0.0795    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    1.5429    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323    0.8816   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866    2.2349   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3258   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -2.3793    0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -2.4308   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -0.9228   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  9 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 14  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.090  -6.383   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.653  -5.299   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.136   6.045   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.802   3.735   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.802   2.195   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.811  -3.731   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.381  -1.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.469   2.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.890  -1.020   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.184  -5.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.136   4.505   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.136   1.425   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.136  -0.115   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.906  -2.485   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.469   3.735   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       7.803   4.505   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.366  -2.485   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6   10   14                                                       
CONECT    7   13   14                                                       
CONECT    8   12   15                                                       
CONECT    9   13   17                                                       
CONECT   10    1    2    6                                                  
CONECT   11    3    4   15                                                  
CONECT   12    5    8   13                                                  
CONECT   13    7    9   12                                                  
CONECT   14    6    7   17                                                  
CONECT   15    8   11   16                                                  
CONECT   16   15                                                            
CONECT   17    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036110
HETATM    1  C1  UNL     1       4.613   1.546  -0.273  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.862   0.270  -0.060  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.322  -0.038   1.124  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.606  -1.312   1.226  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.746  -1.625   0.023  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.489  -0.830   0.029  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.351   0.530  -0.071  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.943   0.828  -0.024  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.661  -0.245   0.100  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.140  -0.413   0.194  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.856   0.913   0.129  1.00  0.00           C  
HETATM   12  C11 UNL     1      -5.341   0.630   0.232  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.500   1.595  -1.178  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.799  -1.321   0.138  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.462  -1.483  -1.279  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.706  -0.671  -1.164  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.646  -0.776  -2.008  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.424   2.203   0.604  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.262   2.092  -1.165  1.00  0.00           H  
HETATM   20  H3  UNL     1       5.705   1.342  -0.406  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.446   0.670   1.929  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.899  -1.227   2.095  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.276  -2.185   1.425  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.472  -2.714   0.124  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.143   1.272  -0.173  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.375  -0.930   1.151  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.450  -1.016  -0.676  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.533   1.589   0.958  1.00  0.00           H  
HETATM   29  H12 UNL     1      -5.647   0.133  -0.710  1.00  0.00           H  
HETATM   30  H13 UNL     1      -5.485  -0.080   1.073  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.923   1.543   0.422  1.00  0.00           H  
HETATM   32  H15 UNL     1      -3.332   0.882  -1.990  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.587   2.235  -0.999  1.00  0.00           H  
HETATM   34  H17 UNL     1      -4.317   2.326  -1.391  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.054  -2.379   0.236  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.713  -2.431  -1.776  1.00  0.00           H  
HETATM   37  H20 UNL     1       1.800  -0.923  -2.001  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   16
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6   15   24
CONECT    6    7    7   14
CONECT    7    8   25
CONECT    8    9
CONECT    9   10   14   14
CONECT   10   11   26   27
CONECT   11   12   13   28
CONECT   12   29   30   31
CONECT   13   32   33   34
CONECT   14   35
CONECT   15   16   36   37
CONECT   16   17   17
END

HMDB0036110
     RDKit          3D
(S)-Bilobanone
 37 38  0  0  0  0  0  0  0  0999 V2000
    4.6134    1.5459   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8616    0.2697   -0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3215   -0.0381    1.1236 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -1.3119    1.2257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7462   -1.6249    0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4892   -0.8301    0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3514    0.5297   -0.0713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9431    0.8275   -0.0239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6615   -0.2450    0.1002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403   -0.4127    0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8555    0.9128    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3407    0.6297    0.2325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5002    1.5954   -1.1780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7990   -1.3211    0.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -1.4826   -1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7059   -0.6713   -1.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6460   -0.7756   -2.0076 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4244    2.2034    0.6041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2615    2.0918   -1.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7052    1.3423   -0.4057 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4463    0.6701    1.9294 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988   -1.2269    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2761   -2.1847    1.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4718   -2.7141    0.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1427    1.2716   -0.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3748   -0.9296    1.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.0161   -0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5330    1.5887    0.9583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6474    0.1333   -0.7098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4854   -0.0795    1.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9225    1.5429    0.4221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3323    0.8816   -1.9900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5866    2.2349   -0.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3174    2.3258   -1.3908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0536   -2.3793    0.2356 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7126   -2.4308   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8002   -0.9228   -2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  9 14  2  0
  5 15  1  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
 14  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  7 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bilobanon	HMDB
Bilobanone	HMDB

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

2-methyl-5-[5-(2-methylpropyl)furan-3-yl]cyclohex-2-en-1-one

Traditional Name

2-methyl-5-[5-(2-methylpropyl)furan-3-yl]cyclohex-2-en-1-one

CAS Registry Number

17015-33-7

SMILES

CC(C)CC1=CC(=CO1)C1CC=C(C)C(=O)C1

InChI Identifier

InChI=1S/C15H20O2/c1-10(2)6-14-7-13(9-17-14)12-5-4-11(3)15(16)8-12/h4,7,9-10,12H,5-6,8H2,1-3H3

InChI Key

ORQIZUYAGXZVPI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036110)

Cellular substructure

Membrane (HMDB: HMDB0036110)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036110)

Source

Exogenous

Food

Food (HMDB: HMDB0036110)

Herb and spice

Other seed

Ginkgo nuts (FooDB: FOOD00367)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0036110)

Not Available

Nutrient (HMDB: HMDB0036110)

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	2.88 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	0.028 g/L	ALOGPS
logP	3.9	ALOGPS
logP	3.9	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	19.87	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	30.21 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	69.68 m³·mol⁻¹	ChemAxon
Polarizability	27.42 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]+	155.179	31661259
DarkChem	[M-H]-	157.41	31661259
DeepCCS	[M+H]+	162.353	30932474
DeepCCS	[M-H]-	159.995	30932474
DeepCCS	[M-2H]-	192.881	30932474
DeepCCS	[M+Na]+	168.446	30932474
AllCCS	[M+H]+	154.8	32859911
AllCCS	[M+H-H2O]+	150.9	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	163.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(S)-Bilobanone	CC(C)CC1=CC(=CO1)C1CC=C(C)C(=O)C1	2395.4	Standard polar	33892256
(S)-Bilobanone	CC(C)CC1=CC(=CO1)C1CC=C(C)C(=O)C1	1786.5	Standard non polar	33892256
(S)-Bilobanone	CC(C)CC1=CC(=CO1)C1CC=C(C)C(=O)C1	1833.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(S)-Bilobanone,1TMS,isomer #1	CC1=CCC(C2=COC(CC(C)C)=C2)C=C1O[Si](C)(C)C	1979.1	Semi standard non polar	33892256
(S)-Bilobanone,1TMS,isomer #1	CC1=CCC(C2=COC(CC(C)C)=C2)C=C1O[Si](C)(C)C	1904.1	Standard non polar	33892256
(S)-Bilobanone,1TBDMS,isomer #1	CC1=CCC(C2=COC(CC(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	2228.9	Semi standard non polar	33892256
(S)-Bilobanone,1TBDMS,isomer #1	CC1=CCC(C2=COC(CC(C)C)=C2)C=C1O[Si](C)(C)C(C)(C)C	2086.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Bilobanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-02gc-2920000000-5c74c4536db19df2295e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (S)-Bilobanone 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 - (S)-Bilobanone 10V, Positive-QTOF	splash10-001i-0390000000-78b4762a3deab7583324	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 20V, Positive-QTOF	splash10-0536-6950000000-2ec55eba09ef7d7148a9	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 40V, Positive-QTOF	splash10-0pbc-9400000000-08c0151826641d8717e3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 10V, Negative-QTOF	splash10-001i-0090000000-560f61c054a72adea08b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 20V, Negative-QTOF	splash10-001i-0590000000-cd9511afa4f5f85fc624	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 40V, Negative-QTOF	splash10-0002-5910000000-1ece898468df3eacd3a5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 10V, Positive-QTOF	splash10-001i-2490000000-1ac6d9d8500fccc6ff14	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 20V, Positive-QTOF	splash10-001j-5940000000-c9dace2ebc0b8b62b55d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 40V, Positive-QTOF	splash10-0532-7910000000-4f7dd2bdd968179a44a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 10V, Negative-QTOF	splash10-001i-0090000000-403b175a8d75af9b9dc4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 20V, Negative-QTOF	splash10-001i-0490000000-cced3a019f44a030d9c5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (S)-Bilobanone 40V, Negative-QTOF	splash10-001i-2900000000-8fc4cab95c7227ca1e55	2021-09-24	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

FDB014956

KNApSAcK ID

C00011591

Chemspider ID

35014097

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12308753

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1853641

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (S)-Bilobanone (HMDB0036110)

MOL for HMDB0036110 ((S)-Bilobanone)

3D MOL for HMDB0036110 ((S)-Bilobanone)

3D SDF for HMDB0036110 ((S)-Bilobanone)

3D-SDF for HMDB0036110 ((S)-Bilobanone)

PDB for HMDB0036110 ((S)-Bilobanone)

3D PDB for HMDB0036110 ((S)-Bilobanone)

SMILES for HMDB0036110 ((S)-Bilobanone)

INCHI for HMDB0036110 ((S)-Bilobanone)

Structure for HMDB0036110 ((S)-Bilobanone)

3D Structure for HMDB0036110 ((S)-Bilobanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra