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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:32:19 UTC

Update Date

2022-03-07 02:54:54 UTC

HMDB ID

HMDB0036402

Secondary Accession Numbers

HMDB36402

Metabolite Identification

Common Name

alpha-Bergamotenol

Description

alpha-Bergamotenol, also known as α-bergamotenol, 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 alpha-Bergamotenol.

Structure

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

HMDB0036402
     RDKit          3D
alpha-Bergamotenol
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3602    2.3018    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    0.8440    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8074   -0.0842    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -1.4366    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -1.5908   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820   -0.9522   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.3468   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.4809    0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -0.0589    1.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525   -0.7633   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    0.4207   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.3095   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    0.2931   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371    0.1716   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    0.3919    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2933   -0.7695    1.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4301    2.4617   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404    2.8200   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.6906    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    0.1506    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.1848    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -1.7201    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.6030   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630   -0.9567   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.3501   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574    1.0708   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8688   -0.1868    2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    1.0058    1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.6451    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2698   -0.8159   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -1.7123   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469    0.6714    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    1.2734   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    0.2301   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    0.1049   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.0524   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5378   -0.7060   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550    1.2005    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    0.6427    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783   -1.4368    1.1779 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  1  0
  7  2  1  0
  8  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
M  END


  Mrv0541 02241218162D          

 16 17  0  0  0  0            999 V2000
   -2.1428    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1428    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7170    0.8256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8577   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4292    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020   -0.4118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0020    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7129    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4278    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577    0.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1428   -0.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8577   -1.2367    0.0000 O   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  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  0  0  0  0
  5  6  1  0  0  0  0
  5  8  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036402

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(CO)=C\CCC1(C)C2CC1C(C)=CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)13-7-6-12(2)14(15)9-13/h5-6,13-14,16H,4,7-10H2,1-3H3/b11-5-

> <INCHI_KEY>
JGINTSAQGRHGMG-WZUFQYTHSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.415918820670733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-en-1-ol

> <ALOGPS_LOGP>
4.73

> <JCHEM_LOGP>
3.180604564666668

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.64402351692704

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0797041136961134

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
70.2996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-en-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036402
     RDKit          3D
alpha-Bergamotenol
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3602    2.3018    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    0.8440    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8074   -0.0842    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -1.4366    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -1.5908   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820   -0.9522   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.3468   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.4809    0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -0.0589    1.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525   -0.7633   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    0.4207   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.3095   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    0.2931   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371    0.1716   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    0.3919    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2933   -0.7695    1.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4301    2.4617   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404    2.8200   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.6906    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    0.1506    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.1848    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -1.7201    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.6030   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630   -0.9567   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.3501   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574    1.0708   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8688   -0.1868    2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    1.0058    1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.6451    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2698   -0.8159   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -1.7123   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469    0.6714    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    1.2734   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    0.2301   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    0.1049   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.0524   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5378   -0.7060   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550    1.2005    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    0.6427    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783   -1.4368    1.1779 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  1  0
  7  2  1  0
  8  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  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      -4.000   1.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.000   0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.668  -0.769   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.338   0.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.338   1.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.668   2.309   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.334  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.668   0.771   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.004  -0.769   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.004   0.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.331   0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.665   0.771   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.000   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.334   0.771   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.000  -1.539   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.334  -2.309   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5    9   10                                             
CONECT    5    4    6    8                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    3    5                                                       
CONECT    9    4                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0036402
HETATM    1  C1  UNL     1      -3.360   2.302   0.126  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.052   0.844   0.038  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.807  -0.084   0.611  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.215  -1.437   0.806  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.975  -1.591  -0.002  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.282  -0.952  -1.366  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.853   0.347  -0.714  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.970  -0.481   0.194  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.897  -0.059   1.609  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.353  -0.763  -0.488  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.258   0.421  -0.209  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.577   0.310  -0.800  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.700   0.293  -0.126  1.00  0.00           C  
HETATM   14  C14 UNL     1       5.037   0.172  -0.860  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.692   0.392   1.348  1.00  0.00           C  
HETATM   16  O1  UNL     1       4.293  -0.770   1.873  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.430   2.462  -0.199  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.740   2.820  -0.609  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.260   2.691   1.165  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.821   0.151   0.921  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.951  -2.185   0.369  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.146  -1.720   1.864  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.557  -2.603  -0.072  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.363  -0.957  -1.617  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.604  -1.350  -2.118  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.357   1.071  -1.352  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.869  -0.187   2.104  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.624   1.006   1.765  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.145  -0.645   2.171  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.270  -0.816  -1.591  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.745  -1.712  -0.131  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.147   0.671   0.829  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.742   1.273  -0.770  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.694   0.230  -1.911  1.00  0.00           H  
HETATM   35  H19 UNL     1       4.867   0.105  -1.933  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.666   1.052  -0.613  1.00  0.00           H  
HETATM   37  H21 UNL     1       5.538  -0.706  -0.410  1.00  0.00           H  
HETATM   38  H22 UNL     1       4.455   1.201   1.594  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.768   0.643   1.828  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.478  -1.437   1.178  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    7
CONECT    3    4   20
CONECT    4    5   21   22
CONECT    5    6    8   23
CONECT    6    7   24   25
CONECT    7    8   26
CONECT    8    9   10
CONECT    9   27   28   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   13   34
CONECT   13   14   15
CONECT   14   35   36   37
CONECT   15   16   38   39
CONECT   16   40
END

HMDB0036402
     RDKit          3D
alpha-Bergamotenol
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.3602    2.3018    0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523    0.8440    0.0384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8074   -0.0842    0.6107 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2155   -1.4366    0.8059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9749   -1.5908   -0.0017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2820   -0.9522   -1.3658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8527    0.3468   -0.7141 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9698   -0.4809    0.1939 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8973   -0.0589    1.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3525   -0.7633   -0.4878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2576    0.4207   -0.2092 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5771    0.3095   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6996    0.2931   -0.1265 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0371    0.1716   -0.8597 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6922    0.3919    1.3476 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2933   -0.7695    1.8730 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4301    2.4617   -0.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404    2.8200   -0.6086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2602    2.6906    1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8211    0.1506    0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9510   -2.1848    0.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -1.7201    1.8643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5567   -2.6030   -0.0719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3630   -0.9567   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6039   -1.3501   -2.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3574    1.0708   -1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8688   -0.1868    2.1042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6239    1.0058    1.7647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.6451    2.1707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2698   -0.8159   -1.5911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7450   -1.7123   -0.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1469    0.6714    0.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    1.2734   -0.7697 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6936    0.2301   -1.9111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8669    0.1049   -1.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6663    1.0524   -0.6127 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5378   -0.7060   -0.4096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4550    1.2005    1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7683    0.6427    1.8283 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4783   -1.4368    1.1779 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  1  0
  7  2  1  0
  8  5  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Bergamotenol	Generator
Α-bergamotenol	Generator
(Z)-alpha-trans-Bergamotol	HMDB
(Z)-trans- alpha-Bergamotol	HMDB
(Z,e)- alpha-Bergamotol	HMDB
9(10)Z,alpha-trans-Bergamotenol	HMDB
trans-(Z)-alpha-Bergamotol	HMDB
Bergamotenol	MeSH

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

(2Z)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-en-1-ol

Traditional Name

(2Z)-5-{2,6-dimethylbicyclo[3.1.1]hept-2-en-6-yl}-2-methylpent-2-en-1-ol

CAS Registry Number

88034-74-6

SMILES

C\C(CO)=C\CCC1(C)C2CC1C(C)=CC2

InChI Identifier

InChI=1S/C15H24O/c1-11(10-16)5-4-8-15(3)13-7-6-12(2)14(15)9-13/h5-6,13-14,16H,4,7-10H2,1-3H3/b11-5-

InChI Key

JGINTSAQGRHGMG-WZUFQYTHSA-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

Pinane monoterpenoid
Bicyclic monoterpenoid
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036402)
Cell membrane (HMDB: HMDB0036402)

Cellular substructure

Extracellular (HMDB: HMDB0036402)
Membrane (HMDB: HMDB0036402)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036402)

Source

Endogenous

Endogenous (HMDB: HMDB0036402)

Plant

Poaceae (HMDB: HMDB0036402)

Animal

Animal (HMDB: HMDB0036402)

Exogenous

Food

Food (HMDB: HMDB0036402)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036402)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036402)

Cellular process

Cell signaling (HMDB: HMDB0036402)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036402)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036402)

Nutrient

Nutrient (HMDB: HMDB0036402)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036402)

Food and nutrition

Food additive

Flavoring agent

Flavoring agent (HMDB: HMDB0036402)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.059 g/L	ALOGPS
logP	4.73	ALOGPS
logP	3.18	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.3 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]+	151.966	31661259
DarkChem	[M-H]-	148.635	31661259
DeepCCS	[M+H]+	163.122	30932474
DeepCCS	[M-H]-	160.765	30932474
DeepCCS	[M-2H]-	194.061	30932474
DeepCCS	[M+Na]+	169.561	30932474
AllCCS	[M+H]+	153.7	32859911
AllCCS	[M+H-H2O]+	149.9	32859911
AllCCS	[M+NH4]+	157.1	32859911
AllCCS	[M+Na]+	158.1	32859911
AllCCS	[M-H]-	161.3	32859911
AllCCS	[M+Na-2H]-	161.9	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Bergamotenol	C\C(CO)=C\CCC1(C)C2CC1C(C)=CC2	2246.8	Standard polar	33892256
alpha-Bergamotenol	C\C(CO)=C\CCC1(C)C2CC1C(C)=CC2	1673.4	Standard non polar	33892256
alpha-Bergamotenol	C\C(CO)=C\CCC1(C)C2CC1C(C)=CC2	1705.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Bergamotenol,1TMS,isomer #1	CC1=CCC2CC1C2(C)CC/C=C(/C)CO[Si](C)(C)C	1840.8	Semi standard non polar	33892256
alpha-Bergamotenol,1TBDMS,isomer #1	CC1=CCC2CC1C2(C)CC/C=C(/C)CO[Si](C)(C)C(C)(C)C	2089.3	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 - alpha-Bergamotenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-9720000000-8e98ef67a24116aad887	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Bergamotenol GC-MS (1 TMS) - 70eV, Positive	splash10-0fi9-9850000000-922c9f80778f8f7cceb1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Bergamotenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Bergamotenol 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 - alpha-Bergamotenol 10V, Positive-QTOF	splash10-0fk9-1290000000-82764a51158cd9b7d75d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 20V, Positive-QTOF	splash10-0uk9-5970000000-be489f0877bb6451bc61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 40V, Positive-QTOF	splash10-01ba-6900000000-c50de81da86dbb4007cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 10V, Negative-QTOF	splash10-014i-0090000000-e74a176c8ddb06d3a6b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 20V, Negative-QTOF	splash10-014i-0390000000-8a4440d787016e7cad90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 40V, Negative-QTOF	splash10-059i-4910000000-c8d5eed82e028e5724f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 10V, Positive-QTOF	splash10-00di-2960000000-3237be9d70df67f8498c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 20V, Positive-QTOF	splash10-00di-3910000000-b237451ecb98777defd7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 40V, Positive-QTOF	splash10-0159-9100000000-27022f255758c942fce1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 20V, Negative-QTOF	splash10-014i-0090000000-1b63a22300aa2b674428	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Bergamotenol 40V, Negative-QTOF	splash10-014i-0960000000-f6e79dbba4004cb28c3c	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

FDB015281

KNApSAcK ID

C00029348

Chemspider ID

4519955

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5368743

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1458111

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 alpha-Bergamotenol (HMDB0036402)

MOL for HMDB0036402 (alpha-Bergamotenol)

3D MOL for HMDB0036402 (alpha-Bergamotenol)

3D SDF for HMDB0036402 (alpha-Bergamotenol)

3D-SDF for HMDB0036402 (alpha-Bergamotenol)

PDB for HMDB0036402 (alpha-Bergamotenol)

3D PDB for HMDB0036402 (alpha-Bergamotenol)

SMILES for HMDB0036402 (alpha-Bergamotenol)

INCHI for HMDB0036402 (alpha-Bergamotenol)

Structure for HMDB0036402 (alpha-Bergamotenol)

3D Structure for HMDB0036402 (alpha-Bergamotenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra