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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:28:32 UTC

Update Date

2022-03-07 02:55:40 UTC

HMDB ID

HMDB0038195

Secondary Accession Numbers

HMDB38195

Metabolite Identification

Common Name

Xanthorrhizol

Description

Xanthorrhizol 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 Xanthorrhizol.

Structure

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

HMDB0038195
     RDKit          3D
Xanthorrhizol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.0020   -1.0787    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.1806    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    1.2534    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208   -0.6395    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4478    0.2752    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913    0.3046   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    1.2136   -1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    1.1400   -2.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    0.7538   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    1.6275    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    1.2492    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.0271    1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.4942    1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -0.9171    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859   -2.1919   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.4987   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.5137    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221   -1.8064   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -1.6654    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    1.4850    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1174    1.5010    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912    1.8993    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -1.6905   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -0.1732    0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    1.2763    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -0.7044   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    0.7077   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    2.2341   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9749   -3.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.2065   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749    1.9927   -3.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.6322    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4810    1.9295    1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398   -1.2986    2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5453   -0.8929    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    0.3342    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -2.4416    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751   -1.1716   -1.3790 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  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  9  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
M  END


  Mrv0541 05061310172D          

 16 16  0  0  0  0            999 V2000
   -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
    1.4289    2.4750    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    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
    0.0000    2.4750    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
    1.4289    0.8250    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
   -0.7145    4.5375    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
    0.7145   -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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  2  0  0  0  0
 12  3  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 10  2  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 13  2  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038195

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3

> <INCHI_KEY>
FKWGCEDRLNNZOZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.063389183292504

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-(6-methylhept-5-en-2-yl)phenol

> <ALOGPS_LOGP>
5.64

> <JCHEM_LOGP>
5.0878253093333345

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.41717718532451

> <JCHEM_PKA_STRONGEST_BASIC>
-5.466329342299741

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
71.0735

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(6-methylhept-5-en-2-yl)phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038195
     RDKit          3D
Xanthorrhizol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.0020   -1.0787    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.1806    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    1.2534    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208   -0.6395    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4478    0.2752    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913    0.3046   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    1.2136   -1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    1.1400   -2.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    0.7538   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    1.6275    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    1.2492    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.0271    1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.4942    1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -0.9171    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859   -2.1919   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.4987   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.5137    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221   -1.8064   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -1.6654    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    1.4850    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1174    1.5010    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912    1.8993    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -1.6905   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -0.1732    0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    1.2763    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -0.7044   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    0.7077   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    2.2341   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9749   -3.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.2065   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749    1.9927   -3.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.6322    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4810    1.9295    1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398   -1.2986    2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5453   -0.8929    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    0.3342    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -2.4416    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751   -1.1716   -1.3790 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  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  9  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11                                                       
CONECT    7    5   12                                                       
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10   14   15                                                       
CONECT   11    1    2    6                                                  
CONECT   12    3    7   14                                                  
CONECT   13    4    8   15                                                  
CONECT   14    9   10   12                                                  
CONECT   15   10   13   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0038195
HETATM    1  C1  UNL     1      -5.002  -1.079   0.633  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.818  -0.181   0.567  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.037   1.253   0.924  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.621  -0.640   0.206  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.448   0.275   0.146  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.891   0.305  -1.261  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.298   1.214  -1.384  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.746   1.140  -2.849  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.442   0.754  -0.558  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.974   1.627   0.359  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.054   1.249   1.165  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.577  -0.027   1.021  1.00  0.00           C  
HETATM   13  C13 UNL     1       4.726  -0.494   1.846  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.061  -0.917   0.111  1.00  0.00           C  
HETATM   15  O1  UNL     1       3.586  -2.192  -0.032  1.00  0.00           O  
HETATM   16  C15 UNL     1       1.994  -0.499  -0.664  1.00  0.00           C  
HETATM   17  H1  UNL     1      -5.941  -0.514   0.606  1.00  0.00           H  
HETATM   18  H2  UNL     1      -5.022  -1.806  -0.200  1.00  0.00           H  
HETATM   19  H3  UNL     1      -5.010  -1.665   1.594  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.546   1.485   1.901  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.117   1.501   0.946  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.591   1.899   0.135  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.536  -1.691  -0.039  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.665  -0.173   0.796  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.687   1.276   0.495  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.652  -0.704  -1.627  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.682   0.708  -1.928  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.016   2.234  -1.141  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.118   0.975  -3.512  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.366   0.207  -2.920  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.375   1.993  -3.116  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.603   2.632   0.511  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.481   1.929   1.891  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.440  -1.299   2.548  1.00  0.00           H  
HETATM   35  H19 UNL     1       5.545  -0.893   1.213  1.00  0.00           H  
HETATM   36  H20 UNL     1       5.161   0.334   2.438  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.365  -2.442   0.561  1.00  0.00           H  
HETATM   38  H22 UNL     1       1.575  -1.172  -1.379  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   28
CONECT    8   29   30   31
CONECT    9   10   10   16
CONECT   10   11   32
CONECT   11   12   12   33
CONECT   12   13   14
CONECT   13   34   35   36
CONECT   14   15   16   16
CONECT   15   37
CONECT   16   38
END

HMDB0038195
     RDKit          3D
Xanthorrhizol
 38 38  0  0  0  0  0  0  0  0999 V2000
   -5.0020   -1.0787    0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8178   -0.1806    0.5671 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0375    1.2534    0.9237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6208   -0.6395    0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4478    0.2752    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8913    0.3046   -1.2611 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2977    1.2136   -1.3836 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7461    1.1400   -2.8491 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4416    0.7538   -0.5583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9740    1.6275    0.3587 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540    1.2492    1.1652 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5773   -0.0271    1.0206 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7255   -0.4942    1.8463 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0613   -0.9171    0.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5859   -2.1919   -0.0322 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9945   -0.4987   -0.6641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9411   -0.5137    0.6064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221   -1.8064   -0.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0099   -1.6654    1.5937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    1.4850    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1174    1.5010    0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5912    1.8993    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5359   -1.6905   -0.0394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650   -0.1732    0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6869    1.2763    0.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6518   -0.7044   -1.6272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6824    0.7077   -1.9276 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0163    2.2341   -1.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1183    0.9749   -3.5120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3657    0.2065   -2.9199 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3749    1.9927   -3.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6035    2.6322    0.5106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4810    1.9295    1.8907 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4398   -1.2986    2.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5453   -0.8929    1.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1612    0.3342    2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3647   -2.4416    0.5608 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5751   -1.1716   -1.3790 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  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
 16  9  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 15 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol	HMDB
(R)-(-)-Xanthorrhizol	HMDB
(R)-5-(1,5-Dimethyl-4-hexenyl)-O-cresol	HMDB
(R)-5-(1-5-Dimethyl-4-hexenyl)-2-methylphenol	HMDB
5-(1,5-Dimethyl-4-hexenyl)-(-)-O-cresol	HMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methyl-(-)-phenol	HMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol	HMDB
5-(1,5-Dimethyl-4-hexenyl)-2-methylphenol, 9ci	HMDB
5-[(1R)-1,5-Dimethyl-4-hexenyl]-2-methyl-phenol	HMDB

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

2-methyl-5-(6-methylhept-5-en-2-yl)phenol

Traditional Name

2-methyl-5-(6-methylhept-5-en-2-yl)phenol

CAS Registry Number

30199-26-9

SMILES

CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1

InChI Identifier

InChI=1S/C15H22O/c1-11(2)6-5-7-12(3)14-9-8-13(4)15(16)10-14/h6,8-10,12,16H,5,7H2,1-4H3

InChI Key

FKWGCEDRLNNZOZ-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
P-cymene
O-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038195)

Source

Endogenous

Endogenous (HMDB: HMDB0038195)

Plant

Plant (HMDB: HMDB0038195)

Animal

Animal (HMDB: HMDB0038195)

Exogenous

Food

Food (HMDB: HMDB0038195)

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0038195)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038195)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038195)

Lipid metabolism pathway (HMDB: HMDB0038195)

Cellular process

Cell signaling (HMDB: HMDB0038195)

Biochemical process

Lipid transport (HMDB: HMDB0038195)

Role

Biological role

Energy source (HMDB: HMDB0038195)

Industrial application

Pharmaceutical industry

Antimicrobial agent (HMDB: HMDB0038195)

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038195)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	326.00 to 327.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.45 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.480	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	5.64	ALOGPS
logP	5.09	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	10.42	ChemAxon
pKa (Strongest Basic)	-5.5	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	71.07 m³·mol⁻¹	ChemAxon
Polarizability	27.06 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	154.94	31661259
DarkChem	[M-H]-	151.674	31661259
DeepCCS	[M+H]+	160.474	30932474
DeepCCS	[M-H]-	158.116	30932474
DeepCCS	[M-2H]-	191.103	30932474
DeepCCS	[M+Na]+	166.567	30932474
AllCCS	[M+H]+	150.7	32859911
AllCCS	[M+H-H2O]+	146.7	32859911
AllCCS	[M+NH4]+	154.4	32859911
AllCCS	[M+Na]+	155.5	32859911
AllCCS	[M-H]-	155.8	32859911
AllCCS	[M+Na-2H]-	156.2	32859911
AllCCS	[M+HCOO]-	156.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	8.89 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1312 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.62 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	26.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2429.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	559.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	230.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	324.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	330.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	813.4 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	747.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	76.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1587.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	642.7 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	1482.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	543.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	454.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	365.1 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Xanthorrhizol	CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1	2623.7	Standard polar	33892256
Xanthorrhizol	CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1	1683.1	Standard non polar	33892256
Xanthorrhizol	CC(CCC=C(C)C)C1=CC(O)=C(C)C=C1	1747.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Xanthorrhizol,1TMS,isomer #1	CC(C)=CCCC(C)C1=CC=C(C)C(O[Si](C)(C)C)=C1	1757.7	Semi standard non polar	33892256
Xanthorrhizol,1TBDMS,isomer #1	CC(C)=CCCC(C)C1=CC=C(C)C(O[Si](C)(C)C(C)(C)C)=C1	2003.2	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 - Xanthorrhizol GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-5910000000-bbbc808402d4ed1b9d87	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthorrhizol GC-MS (1 TMS) - 70eV, Positive	splash10-05di-9380000000-5efc594d791232cfba9e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Xanthorrhizol 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 - Xanthorrhizol 10V, Positive-QTOF	splash10-014i-1490000000-7b7917bbd2d076a6a1bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOF	splash10-014i-3930000000-f36e65d14851d985f07c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOF	splash10-0ldi-9500000000-5dae3bd921c5b051d077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOF	splash10-014i-0090000000-e9ece6fa864d7f85bd6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOF	splash10-014i-0190000000-825f4354c46942faba2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOF	splash10-0zgr-2920000000-ed263b9c3352ae00c36f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Negative-QTOF	splash10-014i-0690000000-832a55e37cc53c279022	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Negative-QTOF	splash10-001i-0900000000-9c4703d7c228cc18545c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 10V, Positive-QTOF	splash10-0a4i-9500000000-6361694e7914d5c8167b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 20V, Positive-QTOF	splash10-05ox-9200000000-ded2bd26eb1ced7c2c22	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Xanthorrhizol 40V, Positive-QTOF	splash10-052f-9600000000-92500c706afd0d6d2d87	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB017434

KNApSAcK ID

C00011622

Chemspider ID

453998

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

520468

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1516951

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Mustaffa F, Indurkar J, Ismail S, Shah M, Mansor SM: An antimicrobial compound isolated from Cinnamomum iners leaves with activity against methicillin-resistant Staphylococcus aureus. Molecules. 2011 Apr 8;16(4):3037-47. doi: 10.3390/molecules16043037. [PubMed:21478819 ]
Handayani T, Sakinah S, Nallappan M, Pihie AH: Regulation of p53-, Bcl-2- and caspase-dependent signaling pathway in xanthorrhizol-induced apoptosis of HepG2 hepatoma cells. Anticancer Res. 2007 Mar-Apr;27(2):965-71. [PubMed:17465228 ]
Lee LY, Shim JS, Rukayadi Y, Hwang JK: Antibacterial activity of xanthorrhizol isolated from Curcuma xanthorrhiza Roxb. against foodborne pathogens. J Food Prot. 2008 Sep;71(9):1926-30. [PubMed:18810881 ]
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 Xanthorrhizol (HMDB0038195)

MOL for HMDB0038195 (Xanthorrhizol)

3D MOL for HMDB0038195 (Xanthorrhizol)

3D SDF for HMDB0038195 (Xanthorrhizol)

3D-SDF for HMDB0038195 (Xanthorrhizol)

PDB for HMDB0038195 (Xanthorrhizol)

3D PDB for HMDB0038195 (Xanthorrhizol)

SMILES for HMDB0038195 (Xanthorrhizol)

INCHI for HMDB0038195 (Xanthorrhizol)

Structure for HMDB0038195 (Xanthorrhizol)

3D Structure for HMDB0038195 (Xanthorrhizol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra