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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:31:43 UTC

Update Date

2022-03-07 02:54:54 UTC

HMDB ID

HMDB0036392

Secondary Accession Numbers

HMDB36392

Metabolite Identification

Common Name

(Z)-alpha-Bergamotenoic acid

Description

(Z)-alpha-Bergamotenoic acid, also known as (Z)-a-bergamotenoate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review a small amount of articles have been published on (Z)-alpha-Bergamotenoic acid.

Structure

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

HMDB0036392
     RDKit          3D
(Z)-alpha-Bergamotenoic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.9865    2.0982    1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    0.8084    0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -0.0999    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -1.4627    1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5302   -1.4767   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9145   -0.9321   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2437    0.4536   -0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736   -0.2447   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -0.3578   -2.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3205   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.7270   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826   -0.6024   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.3062    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5948    1.5018    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652    0.1338    0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818    1.0547    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -0.9497    0.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127    2.0200    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    2.4590    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    2.8999    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452    0.1171    2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.9022    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -2.1113    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869   -2.4361   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673   -1.1923   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7089   -1.1164   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    1.1905   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    0.5166   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.2246   -3.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -1.3246   -2.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    0.6846    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    1.1858   -1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -1.0675   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.6623   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.4563   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808    2.1344    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    2.0778    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.1721    1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036   -1.7883    1.0467 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  7  2  1  0
  8  5  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
  6 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
M  END


  Mrv0541 02241208562D          

 17 18  0  0  0  0            999 V2000
   -2.5000    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0743   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0743    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    1.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2149   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596   -0.6185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3596    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3552   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0701    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -0.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7851   -1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2149   -0.2060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000    1.0311    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7865    0.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 17  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 13 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036392

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(=C/CCC1(C)C2CC1C(C)=CC2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-10-6-7-12-9-13(10)15(12,3)8-4-5-11(2)14(16)17/h5-6,12-13H,4,7-9H2,1-3H3,(H,16,17)/b11-5+

> <INCHI_KEY>
CTORLPNPQPAKGI-VZUCSPMQSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.663151282286197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
3.6530683203333334

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.058317348962378

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
70.2421

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036392
     RDKit          3D
(Z)-alpha-Bergamotenoic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.9865    2.0982    1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    0.8084    0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -0.0999    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -1.4627    1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5302   -1.4767   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9145   -0.9321   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2437    0.4536   -0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736   -0.2447   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -0.3578   -2.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3205   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.7270   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826   -0.6024   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.3062    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5948    1.5018    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652    0.1338    0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818    1.0547    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -0.9497    0.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127    2.0200    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    2.4590    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    2.8999    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452    0.1171    2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.9022    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -2.1113    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869   -2.4361   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673   -1.1923   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7089   -1.1164   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    1.1905   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    0.5166   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.2246   -3.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -1.3246   -2.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    0.6846    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    1.1858   -1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -1.0675   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.6623   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.4563   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808    2.1344    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    2.0778    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.1721    1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036   -1.7883    1.0467 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  7  2  1  0
  8  5  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
  6 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  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      -4.667   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.667  -0.385   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.335  -1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.005  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.005   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.335   1.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.001  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.671  -1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.671   0.385   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.663  -0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.998   0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.332  -0.385   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.667   0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.332  -1.925   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.001  -0.385   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       4.667   1.925   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.335   0.385   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   17                                                  
CONECT    4    3    5    8    9                                             
CONECT    5    4    6   17                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    4                                                            
CONECT    9    4   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17    3    5                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036392
HETATM    1  C1  UNL     1      -2.986   2.098   1.091  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.386   0.808   0.708  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.945  -0.100   1.566  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.573  -1.463   1.066  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.530  -1.477  -0.426  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.915  -0.932  -0.872  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.244   0.454  -0.726  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.974  -0.245  -1.037  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.783  -0.358  -2.543  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.313   0.320  -0.438  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.332  -0.727  -0.602  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.683  -0.602  -0.140  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.314   0.306   0.560  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.595   1.502   1.035  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.765   0.134   0.880  1.00  0.00           C  
HETATM   16  O1  UNL     1       5.282   1.055   1.554  1.00  0.00           O  
HETATM   17  O2  UNL     1       5.493  -0.950   0.472  1.00  0.00           O  
HETATM   18  H1  UNL     1      -3.513   2.020   2.085  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.748   2.459   0.385  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.218   2.900   1.220  1.00  0.00           H  
HETATM   21  H4  UNL     1      -1.845   0.117   2.623  1.00  0.00           H  
HETATM   22  H5  UNL     1      -0.719  -1.902   1.583  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.455  -2.111   1.367  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.287  -2.436  -0.890  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.167  -1.192  -1.909  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.709  -1.116  -0.135  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.625   1.190  -1.445  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.179   0.517  -2.858  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.775  -0.225  -3.063  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.381  -1.325  -2.854  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.159   0.685   0.568  1.00  0.00           H  
HETATM   32  H15 UNL     1       0.571   1.186  -1.107  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.277  -1.067  -1.694  1.00  0.00           H  
HETATM   34  H17 UNL     1       0.906  -1.662  -0.086  1.00  0.00           H  
HETATM   35  H18 UNL     1       3.390  -1.456  -0.421  1.00  0.00           H  
HETATM   36  H19 UNL     1       3.381   2.134   1.547  1.00  0.00           H  
HETATM   37  H20 UNL     1       2.050   2.078   0.306  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.944   1.172   1.894  1.00  0.00           H  
HETATM   39  H22 UNL     1       5.504  -1.788   1.047  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    7
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6    8   24
CONECT    6    7   25   26
CONECT    7    8   27
CONECT    8    9   10
CONECT    9   28   29   30
CONECT   10   11   31   32
CONECT   11   12   33   34
CONECT   12   13   13   35
CONECT   13   14   15
CONECT   14   36   37   38
CONECT   15   16   16   17
CONECT   17   39
END

HMDB0036392
     RDKit          3D
(Z)-alpha-Bergamotenoic acid
 39 40  0  0  0  0  0  0  0  0999 V2000
   -2.9865    2.0982    1.0910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3863    0.8084    0.7078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -0.0999    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5725   -1.4627    1.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5302   -1.4767   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9145   -0.9321   -0.8716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2437    0.4536   -0.7261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9736   -0.2447   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7832   -0.3578   -2.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3132    0.3205   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3325   -0.7270   -0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6826   -0.6024   -0.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3140    0.3062    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5948    1.5018    1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7652    0.1338    0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818    1.0547    1.5536 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4928   -0.9497    0.4725 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5127    2.0200    2.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7482    2.4590    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2180    2.8999    1.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8452    0.1171    2.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191   -1.9022    1.5828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4555   -2.1113    1.3665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2869   -2.4361   -0.8896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1673   -1.1923   -1.9091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7089   -1.1164   -0.1353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6254    1.1905   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1787    0.5166   -2.8583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7751   -0.2246   -3.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3808   -1.3246   -2.8540 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1586    0.6846    0.5679 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5708    1.1858   -1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2769   -1.0675   -1.6936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -1.6623   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3905   -1.4563   -0.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3808    2.1344    1.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0495    2.0778    0.3058 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9435    1.1721    1.8939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5036   -1.7883    1.0467 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  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
  7  2  1  0
  8  5  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
  6 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-a-Bergamotenoate	Generator
(Z)-a-Bergamotenoic acid	Generator
(Z)-alpha-Bergamotenoate	Generator
(Z)-Α-bergamotenoate	Generator
(Z)-Α-bergamotenoic acid	Generator
(2E)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoate	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

(2E)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

Traditional Name

(2E)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-enoic acid

CAS Registry Number

124439-27-6

SMILES

C\C(=C/CCC1(C)C2CC1C(C)=CC2)C(O)=O

InChI Identifier

InChI=1S/C15H22O2/c1-10-6-7-12-9-13(10)15(12,3)8-4-5-11(2)14(16)17/h5-6,12-13H,4,7-9H2,1-3H3,(H,16,17)/b11-5+

InChI Key

CTORLPNPQPAKGI-VZUCSPMQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Pinane monoterpenoid
Medium-chain fatty acid
Branched fatty acid
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
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: HMDB0036392)

Source

Endogenous

Endogenous (HMDB: HMDB0036392)

Animal

Animal (HMDB: HMDB0036392)

Exogenous

Food

Food (HMDB: HMDB0036392)

Exogenous (HMDB: HMDB0036392)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036392)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036392)

Lipid metabolism pathway (HMDB: HMDB0036392)

Cellular process

Cell signaling (HMDB: HMDB0036392)

Biochemical process

Lipid transport (HMDB: HMDB0036392)

Role

Biological role

Energy source (HMDB: HMDB0036392)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036392)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036392)

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	2.02 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	0.035 g/L	ALOGPS
logP	4.5	ALOGPS
logP	3.65	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.06	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.24 m³·mol⁻¹	ChemAxon
Polarizability	27.66 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]+	157.527	31661259
DarkChem	[M-H]-	153.48	31661259
DeepCCS	[M+H]+	163.773	30932474
DeepCCS	[M-H]-	161.415	30932474
DeepCCS	[M-2H]-	194.301	30932474
DeepCCS	[M+Na]+	169.866	30932474
AllCCS	[M+H]+	156.4	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	163.3	32859911
AllCCS	[M+HCOO]-	163.8	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.	7.05 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3224 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.49 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2336.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	372.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	187.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	159.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	463.9 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	571.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1175.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	450.0 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	1116.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	318.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	384.7 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	29.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(Z)-alpha-Bergamotenoic acid	C\C(=C/CCC1(C)C2CC1C(C)=CC2)C(O)=O	2829.7	Standard polar	33892256
(Z)-alpha-Bergamotenoic acid	C\C(=C/CCC1(C)C2CC1C(C)=CC2)C(O)=O	1789.3	Standard non polar	33892256
(Z)-alpha-Bergamotenoic acid	C\C(=C/CCC1(C)C2CC1C(C)=CC2)C(O)=O	1887.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-alpha-Bergamotenoic acid,1TMS,isomer #1	CC1=CCC2CC1C2(C)CC/C=C(\C)C(=O)O[Si](C)(C)C	1912.2	Semi standard non polar	33892256
(Z)-alpha-Bergamotenoic acid,1TBDMS,isomer #1	CC1=CCC2CC1C2(C)CC/C=C(\C)C(=O)O[Si](C)(C)C(C)(C)C	2154.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-alpha-Bergamotenoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fr6-9620000000-58bb209660e8311b169a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-alpha-Bergamotenoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9330000000-4ca7c7a9401ffbee3c50	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-alpha-Bergamotenoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-alpha-Bergamotenoic acid 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 - (Z)-alpha-Bergamotenoic acid 10V, Positive-QTOF	splash10-000i-1690000000-329dcdd1e0e6e9918a56	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 20V, Positive-QTOF	splash10-01p9-1910000000-049ae494abcbd6fc84af	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 40V, Positive-QTOF	splash10-0gia-5900000000-a0ad23965f2d8ed66b42	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 10V, Negative-QTOF	splash10-001i-0190000000-444f9d1e3fbd86798b80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 20V, Negative-QTOF	splash10-001r-1970000000-e942c3c44edf8462b5b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 40V, Negative-QTOF	splash10-00dr-4910000000-8d14175169a96b0bf8b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 10V, Positive-QTOF	splash10-01bi-2930000000-2a96e0d5adffea0c17ad	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 20V, Positive-QTOF	splash10-00di-2900000000-2d5b4d369376c89700a0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 40V, Positive-QTOF	splash10-014i-9300000000-00e84a13b12a6c5d8eac	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 20V, Negative-QTOF	splash10-001i-0890000000-4aa2b1ebe6adcaf05e98	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Bergamotenoic acid 40V, Negative-QTOF	splash10-0910-0910000000-8b8e30719e944d3c5420	2021-09-24	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

FDB015270

KNApSAcK ID

Not Available

Chemspider ID

35014137

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14059031

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1854931

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 (Z)-alpha-Bergamotenoic acid (HMDB0036392)

MOL for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

3D MOL for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

3D SDF for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

3D-SDF for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

PDB for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

3D PDB for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

SMILES for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

INCHI for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

Structure for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

3D Structure for HMDB0036392 ((Z)-alpha-Bergamotenoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra