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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:15:21 UTC

Update Date

2022-03-07 02:54:49 UTC

HMDB ID

HMDB0036197

Secondary Accession Numbers

HMDB36197

Metabolite Identification

Common Name

(-)-alpha-Bisabolol

Description

(-)-alpha-Bisabolol, also known as bisabolol or levomenol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (-)-alpha-bisabolol is considered to be an isoprenoid. Based on a literature review a small amount of articles have been published on (-)-alpha-Bisabolol.

Structure

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

HMDB0036197
     RDKit          3D
(-)-alpha-Bisabolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -4.3580    0.3566    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.1725   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544   -0.0569   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658    0.2020   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471    0.4315   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.7849   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.7212    0.5166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0670   -1.9859    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -0.7634    1.8824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.5182    0.2534 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5068    0.7255   -1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8689    0.1460   -1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    0.4958   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901    0.0102   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384    1.4032    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207    0.6551    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260   -0.4409    1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599    1.3479    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.2239    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    0.4612   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5662   -1.1458   -1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3039    0.3882   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.0684   -2.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131    0.6058    0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142    1.3416   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601   -1.7185   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -0.8195   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9510   -2.7384    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453   -2.4781   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -1.7886    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439   -1.6249    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    1.3909    0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    0.3755   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290    1.8264   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.5043   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8537    0.6701   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.0210   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0393   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737    1.6207    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233    2.3012    0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.3514    1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.2023    2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 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
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  1
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv1652303202019012D          

 17 17  0  0  0  0            999 V2000
 9999.629310000.4122    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.3439 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.057110000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7723 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1987 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510001.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.040910001.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.216010001.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7712 9998.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6293 9999.5877    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
 9998.200610000.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.486110000.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4861 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2006 9998.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9151 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.915110000.0006    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  6  0  0  0
  1  9  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  1 17  1  0  0  0  0
 17 11  1  1  0  0  0
 14 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036197

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1

> <INCHI_KEY>
RGZSQWQPBWRIAQ-CABCVRRESA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.289460303145148

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

> <ALOGPS_LOGP>
4.76

> <JCHEM_LOGP>
3.911965512666667

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4708710633739094

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
72.1875

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bisabolol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036197
     RDKit          3D
(-)-alpha-Bisabolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -4.3580    0.3566    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.1725   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544   -0.0569   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658    0.2020   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471    0.4315   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.7849   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.7212    0.5166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0670   -1.9859    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -0.7634    1.8824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.5182    0.2534 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5068    0.7255   -1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8689    0.1460   -1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    0.4958   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901    0.0102   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384    1.4032    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207    0.6551    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260   -0.4409    1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599    1.3479    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.2239    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    0.4612   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5662   -1.1458   -1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3039    0.3882   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.0684   -2.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131    0.6058    0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142    1.3416   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601   -1.7185   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -0.8195   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9510   -2.7384    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453   -2.4781   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -1.7886    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439   -1.6249    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    1.3909    0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    0.3755   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290    1.8264   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.5043   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8537    0.6701   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.0210   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0393   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737    1.6207    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233    2.3012    0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.3514    1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.2023    2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 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
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  1
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0    8665.9758667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3098666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.6408667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.9758666.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.3068667.436   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.6388666.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.3068668.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8666.7438668.767   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8665.2038668.767   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8660.6408664.358   0.000  0.00  0.00           C+0
HETATM   11  H   UNK     0    8665.9758665.897   0.000  0.00  0.00           H+0
HETATM   12  C   UNK     0    8663.3088667.438   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8661.9748666.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8661.9748665.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.3088664.358   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8664.6428665.128   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.6428666.668   0.000  0.00  0.00           C+0
CONECT    1    2    8    9   17                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9    1                                                            
CONECT   10   14                                                            
CONECT   11   17                                                            
CONECT   12   13   17                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   10                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16    1   11                                             
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0036197
HETATM    1  C1  UNL     1      -4.358   0.357   1.140  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.236   0.173  -0.334  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.454  -0.057  -1.187  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.066   0.202  -0.952  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.847   0.431  -0.100  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.973  -0.785  -0.288  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.280  -0.721   0.517  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.067  -1.986   0.238  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.043  -0.763   1.882  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.058   0.518   0.253  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.507   0.726  -1.149  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.869   0.146  -1.425  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.812   0.496  -0.550  1.00  0.00           C  
HETATM   14  C13 UNL     1       5.190   0.010  -0.688  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.338   1.403   0.558  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.221   0.655   1.242  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.726  -0.441   1.627  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.960   1.348   1.390  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.407   0.224   1.479  1.00  0.00           H  
HETATM   20  H4  UNL     1      -5.280   0.461  -2.143  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.566  -1.146  -1.357  1.00  0.00           H  
HETATM   22  H6  UNL     1      -6.304   0.388  -0.647  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.982   0.068  -2.020  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.113   0.606   0.957  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.314   1.342  -0.489  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.560  -1.718  -0.089  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.716  -0.819  -1.384  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.951  -2.738   1.033  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.745  -2.478  -0.709  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.153  -1.789   0.126  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.444  -1.625   2.140  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.388   1.391   0.514  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.789   0.376  -1.918  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.629   1.826  -1.387  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.064  -0.504  -2.269  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.854   0.670  -0.085  1.00  0.00           H  
HETATM   37  H21 UNL     1       5.467   0.021  -1.767  1.00  0.00           H  
HETATM   38  H22 UNL     1       5.334  -1.039  -0.345  1.00  0.00           H  
HETATM   39  H23 UNL     1       4.174   1.621   1.256  1.00  0.00           H  
HETATM   40  H24 UNL     1       2.923   2.301   0.094  1.00  0.00           H  
HETATM   41  H25 UNL     1       2.622  -0.351   1.506  1.00  0.00           H  
HETATM   42  H26 UNL     1       1.915   1.202   2.143  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   10
CONECT    8   28   29   30
CONECT    9   31
CONECT   10   11   16   32
CONECT   11   12   33   34
CONECT   12   13   13   35
CONECT   13   14   15
CONECT   14   36   37   38
CONECT   15   16   39   40
CONECT   16   41   42
END

HMDB0036197
     RDKit          3D
(-)-alpha-Bisabolol
 42 42  0  0  0  0  0  0  0  0999 V2000
   -4.3580    0.3566    1.1400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2359    0.1725   -0.3341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4544   -0.0569   -1.1872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0658    0.2020   -0.9523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8471    0.4315   -0.0995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9725   -0.7849   -0.2884 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -0.7212    0.5166 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0670   -1.9859    0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0429   -0.7634    1.8824 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0582    0.5182    0.2534 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5068    0.7255   -1.1493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8689    0.1460   -1.4248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8124    0.4958   -0.5503 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1901    0.0102   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3384    1.4032    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2207    0.6551    1.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7260   -0.4409    1.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9599    1.3479    1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4072    0.2239    1.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2805    0.4612   -2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5662   -1.1458   -1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3039    0.3882   -0.6472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9820    0.0684   -2.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1131    0.6058    0.9571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142    1.3416   -0.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5601   -1.7185   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7158   -0.8195   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9510   -2.7384    1.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453   -2.4781   -0.7089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1535   -1.7886    0.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4439   -1.6249    2.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    1.3909    0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7885    0.3755   -1.9176 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6290    1.8264   -1.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0637   -0.5043   -2.2687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8537    0.6701   -0.0854 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4666    0.0210   -1.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3343   -1.0393   -0.3446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1737    1.6207    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9233    2.3012    0.0941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6215   -0.3514    1.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9148    1.2023    2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  1
  7 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
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  1
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Levomenol	Kegg
(-)-a-Bisabolol	Generator
(-)-Α-bisabolol	Generator
Bisabolol, (-)-isomer	HMDB
Bisabolol	HMDB
a-Bisabolol	HMDB
Α-bisabolol	HMDB
(-)-(1's,2S)-alpha-Bisabolol	HMDB
(-)-(1's,2S)-Α-bisabolol	HMDB
(-)-(1’S,2S)-α-bisabolol	HMDB
(-)-(4S,8S)-alpha-Bisabolol	HMDB
(-)-(4S,8S)-Α-bisabolol	HMDB
(AlphaS,1S)-alpha,4-dimethyl-alpha-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol	HMDB
(ΑS,1S)-α,4-dimethyl-α-(4-methyl-3-penten-1-yl)-3-cyclohexene-1-methanol	HMDB
alpha-(-)-Bisabolol	HMDB
L-alpha-Bisabolol	HMDB
L-Α-bisabolol	HMDB
Α-(-)-bisabolol	HMDB
(-)-alpha-Bisabolol	HMDB

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.372

Monoisotopic Molecular Weight

222.198365457

IUPAC Name

(2S)-6-methyl-2-[(1S)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-ol

Traditional Name

bisabolol

CAS Registry Number

23089-26-1

SMILES

[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C

InChI Identifier

InChI=1S/C15H26O/c1-12(2)6-5-11-15(4,16)14-9-7-13(3)8-10-14/h6-7,14,16H,5,8-11H2,1-4H3/t14-,15+/m1/s1

InChI Key

RGZSQWQPBWRIAQ-CABCVRRESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Bisabolane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:125 )
Bisabolane sesquiterpenoids (C09621 )
Bisabolanes (C09621 )
Bisabolane sesquiterpenoids (LMPR0103060001 )

Ontology

Cytoplasm (HMDB: HMDB0036197)
Cell membrane (HMDB: HMDB0036197)

Cellular substructure

Extracellular (HMDB: HMDB0036197)
Membrane (HMDB: HMDB0036197)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036197)

Source

Endogenous

Endogenous (HMDB: HMDB0036197)

Plant

Plant (HMDB: HMDB0036197)

Animal

Animal (HMDB: HMDB0036197)

Exogenous

Food

Food (HMDB: HMDB0036197)

Tea

Herb and spice

Herb

German camomile (FooDB: FOOD00107)

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036197)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036197)

Cellular process

Cell signaling (HMDB: HMDB0036197)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036197)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036197)

Nutrient

Nutrient (HMDB: HMDB0036197)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036197)

Emulsifier (HMDB: HMDB0036197)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	314.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.69 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.592 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.073 g/L	ALOGPS
logP	4.76	ALOGPS
logP	3.91	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-0.47	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	72.19 m³·mol⁻¹	ChemAxon
Polarizability	28.29 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	155.46	30932474
DeepCCS	[M-H]-	153.065	30932474
DeepCCS	[M-2H]-	187.073	30932474
DeepCCS	[M+Na]+	161.838	30932474
AllCCS	[M+H]+	155.8	32859911
AllCCS	[M+H-H2O]+	152.0	32859911
AllCCS	[M+NH4]+	159.3	32859911
AllCCS	[M+Na]+	160.3	32859911
AllCCS	[M-H]-	161.8	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-alpha-Bisabolol	[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C	2140.4	Standard polar	33892256
(-)-alpha-Bisabolol	[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C	1631.9	Standard non polar	33892256
(-)-alpha-Bisabolol	[H][C@@]1(CCC(C)=CC1)[C@@](C)(O)CCC=C(C)C	1663.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-alpha-Bisabolol,1TMS,isomer #1	CC(C)=CCC[C@](C)(O[Si](C)(C)C)[C@@H]1CC=C(C)CC1	1769.1	Semi standard non polar	33892256
(-)-alpha-Bisabolol,1TBDMS,isomer #1	CC(C)=CCC[C@](C)(O[Si](C)(C)C(C)(C)C)[C@@H]1CC=C(C)CC1	2012.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (-)-alpha-Bisabolol GC-EI-Q (Non-derivatized)	splash10-066u-9500000000-198f9627399bbe1a8ae9	2020-07-08	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-alpha-Bisabolol 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-Bisabolol 10V, Positive-QTOF	splash10-0ab9-1290000000-205c7c190671df2e0141	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 20V, Positive-QTOF	splash10-05u2-9730000000-867964dcbacd7531be85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 40V, Positive-QTOF	splash10-0gb9-9400000000-531e5c4b5695ad0e8e09	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 10V, Negative-QTOF	splash10-00di-0090000000-dc36029a7670fe05fa75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 20V, Negative-QTOF	splash10-00di-2190000000-aba6002bf895bc6a5762	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 40V, Negative-QTOF	splash10-0002-9710000000-0aec4bfc3f14d590d3ba	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 20V, Negative-QTOF	splash10-00di-0290000000-4b15d43984c03b619c11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 40V, Negative-QTOF	splash10-0kmi-1940000000-0ccfc6b1df77fb556c03	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 10V, Positive-QTOF	splash10-059j-4920000000-a1ba351b509e5f240f4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 20V, Positive-QTOF	splash10-0a5j-7900000000-1f54ff8424c7d80eebe4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Bisabolol 40V, Positive-QTOF	splash10-0006-9100000000-4ce3d02192df7090cca8	2021-09-22	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

DB13153

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00003103 C00011607

Chemspider ID

390796

KEGG Compound ID

C09621

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442343

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1412691

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-Bisabolol (HMDB0036197)

MOL for HMDB0036197 ((-)-alpha-Bisabolol)

3D MOL for HMDB0036197 ((-)-alpha-Bisabolol)

3D SDF for HMDB0036197 ((-)-alpha-Bisabolol)

3D-SDF for HMDB0036197 ((-)-alpha-Bisabolol)

PDB for HMDB0036197 ((-)-alpha-Bisabolol)

3D PDB for HMDB0036197 ((-)-alpha-Bisabolol)

SMILES for HMDB0036197 ((-)-alpha-Bisabolol)

INCHI for HMDB0036197 ((-)-alpha-Bisabolol)

Structure for HMDB0036197 ((-)-alpha-Bisabolol)

3D Structure for HMDB0036197 ((-)-alpha-Bisabolol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra