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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:13:35 UTC

Update Date

2022-03-07 02:54:48 UTC

HMDB ID

HMDB0036163

Secondary Accession Numbers

HMDB36163

Metabolite Identification

Common Name

beta-Sesquiphellandrene

Description

beta-Sesquiphellandrene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on beta-Sesquiphellandrene.

Structure

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

HMDB0036163
     RDKit          3D
beta-Sesquiphellandrene
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.3929    0.9688    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888    0.9674   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052    0.3298   -1.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -0.2422   -1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -0.1701    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -0.7500   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4502   -2.1926   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.5812    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -1.1791    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.5293   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002    0.1083   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463    0.7317   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849    0.2287    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    1.2638    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    1.6118    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1171    0.5034   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    1.4352    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.3339   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786   -0.7004   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7734    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668   -0.2238   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138   -2.4926   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -2.8819    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -2.2963   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.5018    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -1.0165    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499   -2.2538    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -0.9983    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -0.5746   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771    0.4129   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5130    0.4326   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238    1.8390   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966    0.6673    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    0.8897    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -0.7531    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.9596   -0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.5142    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    2.7046    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    1.2044    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  5 14  1  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

Sesquiphellandrene
  Mrv1572001071617132D          
  Mrv0541 01161314182D          
 15 15  0  0  0  0            999 V2000
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  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
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
  9 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036163

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCC=C(C)C)C1CCC(=C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14-15H,3,5,7,9,11H2,1-2,4H3

> <INCHI_KEY>
PHWISBHSBNDZDX-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.184874313345436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene

> <ALOGPS_LOGP>
5.71

> <JCHEM_LOGP>
4.923184751333333

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
70.5495

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.03e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036163
     RDKit          3D
beta-Sesquiphellandrene
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.3929    0.9688    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888    0.9674   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052    0.3298   -1.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -0.2422   -1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -0.1701    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -0.7500   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4502   -2.1926   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.5812    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -1.1791    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.5293   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002    0.1083   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463    0.7317   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849    0.2287    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    1.2638    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    1.6118    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1171    0.5034   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    1.4352    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.3339   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786   -0.7004   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7734    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668   -0.2238   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138   -2.4926   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -2.8819    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -2.2963   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.5018    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -1.0165    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499   -2.2538    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -0.9983    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -0.5746   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771    0.4129   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5130    0.4326   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238    1.8390   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966    0.6673    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    0.8897    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -0.7531    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.9596   -0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.5142    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    2.7046    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    1.2044    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  5 14  1  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Sesquiphellandrene                                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    2   10   15                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0036163
HETATM    1  C1  UNL     1       5.393   0.969   0.253  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.089   0.967  -0.042  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.605   0.330  -1.263  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.411  -0.242  -1.279  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.661  -0.170   0.002  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.307  -0.750  -0.175  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.450  -2.193  -0.599  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.588  -0.581   1.017  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.957  -1.179   0.811  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.652  -0.529  -0.361  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.800   0.108  -0.224  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.446   0.732  -1.404  1.00  0.00           C  
HETATM   13  C13 UNL     1      -4.485   0.229   1.089  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.688   1.264   0.439  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.099   1.612   0.859  1.00  0.00           C  
HETATM   16  H1  UNL     1       6.117   0.503  -0.396  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.767   1.435   1.151  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.235   0.334  -2.143  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.079  -0.700  -2.181  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.257  -0.773   0.732  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.167  -0.224  -1.056  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.314  -2.493  -1.343  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.477  -2.882   0.275  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.433  -2.296  -1.100  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.737   0.502   1.203  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.163  -1.016   1.926  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.950  -2.254   0.619  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.612  -0.998   1.686  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.214  -0.575  -1.351  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.977   0.413  -2.363  1.00  0.00           H  
HETATM   31  H16 UNL     1      -5.513   0.433  -1.416  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.424   1.839  -1.345  1.00  0.00           H  
HETATM   33  H18 UNL     1      -5.497   0.667   0.979  1.00  0.00           H  
HETATM   34  H19 UNL     1      -3.929   0.890   1.784  1.00  0.00           H  
HETATM   35  H20 UNL     1      -4.633  -0.753   1.583  1.00  0.00           H  
HETATM   36  H21 UNL     1       1.438   1.960  -0.402  1.00  0.00           H  
HETATM   37  H22 UNL     1       1.029   1.514   1.263  1.00  0.00           H  
HETATM   38  H23 UNL     1       3.263   2.705   0.890  1.00  0.00           H  
HETATM   39  H24 UNL     1       3.260   1.204   1.878  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   15
CONECT    3    4    4   18
CONECT    4    5   19
CONECT    5    6   14   20
CONECT    6    7    8   21
CONECT    7   22   23   24
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   11   29
CONECT   11   12   13
CONECT   12   30   31   32
CONECT   13   33   34   35
CONECT   14   15   36   37
CONECT   15   38   39
END

HMDB0036163
     RDKit          3D
beta-Sesquiphellandrene
 39 39  0  0  0  0  0  0  0  0999 V2000
    5.3929    0.9688    0.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0888    0.9674   -0.0421 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6052    0.3298   -1.2628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4113   -0.2422   -1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6611   -0.1701    0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3066   -0.7500   -0.1753 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4502   -2.1926   -0.5986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5885   -0.5812    1.0170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9573   -1.1791    0.8114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6518   -0.5293   -0.3605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8002    0.1083   -0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4463    0.7317   -1.4036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4849    0.2287    1.0892 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6881    1.2638    0.4390 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0989    1.6118    0.8595 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1171    0.5034   -0.3958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7670    1.4352    1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2355    0.3339   -2.1426 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0786   -0.7004   -2.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2566   -0.7734    0.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1668   -0.2238   -1.0559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138   -2.4926   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772   -2.8819    0.2751 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4332   -2.2963   -1.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7374    0.5018    1.2026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1630   -1.0165    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499   -2.2538    0.6194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6118   -0.9983    1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2141   -0.5746   -1.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9771    0.4129   -2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5130    0.4326   -1.4162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4238    1.8390   -1.3453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4966    0.6673    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9293    0.8897    1.7836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6327   -0.7531    1.5833 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4377    1.9596   -0.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0285    1.5142    1.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2634    2.7046    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605    1.2044    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 11 12  1  0
 11 13  1  0
  5 14  1  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  4 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Sesquiphellandrene	Generator
Β-sesquiphellandrene	Generator
3-(1,5-Dimethyl-4-hexenyl)-6-methylene-1-cyclohexene	MetaCyc, HMDB
(-)-beta-Sesquiphellandrene	HMDB
3-(1,5-Dimethyl-4-hexenyl)-6-methylenecyclohexene, 9ci	HMDB
beta-Sesquiphellanderene	HMDB
Sesquiphellandrene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene

Traditional Name

3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene

CAS Registry Number

20307-83-9

SMILES

CC(CCC=C(C)C)C1CCC(=C)C=C1

InChI Identifier

InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14-15H,3,5,7,9,11H2,1-2,4H3

InChI Key

PHWISBHSBNDZDX-UHFFFAOYSA-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
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

a sesquiterpenoid (CPD-8247 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 23454028)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036163)

Source

Endogenous

Endogenous (HMDB: HMDB0036163)

Plant

Plant (HMDB: HMDB0036163)

Animal

Animal (HMDB: HMDB0036163)

Exogenous

Food

Food (HMDB: HMDB0036163)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)
Turmeric (FooDB: FOOD00068)

Herb

Fruit

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Tea

Exogenous (HMDB: HMDB0036163)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036163)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036163)

Lipid metabolism pathway (HMDB: HMDB0036163)

Cellular process

Cell signaling (HMDB: HMDB0036163)

Biochemical process

Lipid transport (HMDB: HMDB0036163)

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036163)

Coloring agent

Fluorescent agent

Expectorant (HMDB: HMDB0036163)

Agriculture

Pesticide (HMDB: HMDB0036163)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	270.00 to 272.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.013 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.522 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.002 g/L	ALOGPS
logP	5.71	ALOGPS
logP	4.92	ChemAxon
logS	-5	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.55 m³·mol⁻¹	ChemAxon
Polarizability	26.18 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
DarkChem	[M+H]+	150.518	31661259
DarkChem	[M-H]-	148.564	31661259
DeepCCS	[M+H]+	152.172	30932474
DeepCCS	[M-H]-	149.814	30932474
DeepCCS	[M-2H]-	185.003	30932474
DeepCCS	[M+Na]+	160.373	30932474
AllCCS	[M+H]+	150.1	32859911
AllCCS	[M+H-H2O]+	146.1	32859911
AllCCS	[M+NH4]+	153.8	32859911
AllCCS	[M+Na]+	154.9	32859911
AllCCS	[M-H]-	156.5	32859911
AllCCS	[M+Na-2H]-	157.3	32859911
AllCCS	[M+HCOO]-	158.2	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.	8.58 minutes	32390414
Predicted by Siyang on May 30, 2022	22.8551 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.46 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2926.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	820.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	307.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	526.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	924.2 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	931.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	143.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1961.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	702.2 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	1635.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	704.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	559.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	559.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	731.6 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Sesquiphellandrene	CC(CCC=C(C)C)C1CCC(=C)C=C1	1716.3	Standard polar	33892256
beta-Sesquiphellandrene	CC(CCC=C(C)C)C1CCC(=C)C=C1	1487.7	Standard non polar	33892256
beta-Sesquiphellandrene	CC(CCC=C(C)C)C1CCC(=C)C=C1	1496.8	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 - beta-Sesquiphellandrene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9400000000-da410262a5aa40a5141e	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Sesquiphellandrene 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 - beta-Sesquiphellandrene 10V, Positive-QTOF	splash10-0a4i-1590000000-ee4910c0211e359eb6d6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Positive-QTOF	splash10-0ce9-5920000000-3de3009aefc4652d9bc3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Positive-QTOF	splash10-0gb9-9400000000-eb663137c6ef2baa559f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Negative-QTOF	splash10-0udi-0090000000-62a38848141bb5a59eb5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Negative-QTOF	splash10-0udi-0190000000-ff4a8c08da39e9922cfb	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Negative-QTOF	splash10-000i-4900000000-1842c3f2bfe51c2cf850	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Positive-QTOF	splash10-05gi-9600000000-56e4e42e5eedecf82f44	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Positive-QTOF	splash10-00kf-9200000000-9e8b6a8db07464f4f724	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Positive-QTOF	splash10-0006-9100000000-3d87fa454ae9477f27fa	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Negative-QTOF	splash10-0udi-0290000000-2cb14f58730ed114d305	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Negative-QTOF	splash10-0udi-4490000000-6bc908356192dde2f972	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	23454028	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Nonalcoholic fatty liver disease	23454028	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519764

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1103651

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nazaruk J, Kalemba D: Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers. Molecules. 2009 Jul 9;14(7):2458-65. doi: 10.3390/molecules14072458. [PubMed:19633616 ]
Zhan K, Wang C, Xu K, Yin H: [Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry]. Se Pu. 2008 Nov;26(6):692-6. [PubMed:19253546 ]
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 beta-Sesquiphellandrene (HMDB0036163)

MOL for HMDB0036163 (beta-Sesquiphellandrene)

3D MOL for HMDB0036163 (beta-Sesquiphellandrene)

3D SDF for HMDB0036163 (beta-Sesquiphellandrene)

3D-SDF for HMDB0036163 (beta-Sesquiphellandrene)

PDB for HMDB0036163 (beta-Sesquiphellandrene)

3D PDB for HMDB0036163 (beta-Sesquiphellandrene)

SMILES for HMDB0036163 (beta-Sesquiphellandrene)

INCHI for HMDB0036163 (beta-Sesquiphellandrene)

Structure for HMDB0036163 (beta-Sesquiphellandrene)

3D Structure for HMDB0036163 (beta-Sesquiphellandrene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra