Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 23:25:16 UTC

Update Date

2021-11-15 21:12:12 UTC

HMDB ID

HMDB0303114

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Patchouli alcohol

Description

Patchouli alcohol is a member of the class of compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). Patchouli alcohol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Patchouli alcohol is a camphor, earthy, and patchouli tasting compound found in ginger, which makes patchouli alcohol a potential biomarker for the consumption of this food product. Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli. Patchouli oil is an important material in perfumery. The (-)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchoulol is also used in the synthesis of the chemotherapy drug Taxol.

Structure

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

HMDB0303114
     RDKit          3D
Patchouli alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.2001    0.6939   -1.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.5329   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3878    1.8050   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126    1.7150    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    0.4518    0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    0.3728    2.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.3267   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9844    1.5551   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -0.1923    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7262   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -2.1081   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -2.0528    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.7390    0.8121 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2615   -0.8217    2.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323   -0.6071   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.4218   -1.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481    0.5722   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -0.0944   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623    1.6913   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    0.3434    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    2.5517    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    2.2029   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539    2.5890    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    1.8823    1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -0.5433    2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727    2.1541   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    1.2439   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2017    2.2362   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.6505    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -0.3275   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.0504    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8004   -0.7248   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -2.4147   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -2.8088   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -2.3628    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -2.8255    0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686   -1.4567    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -1.3722    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5295    0.1425    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -1.5567   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    0.6018   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -1.1084   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15  2  1  0
 13  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

  Mrv0541 02241220452D          

 16 18  0  0  1  0            999 V2000
    1.7746    0.0835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -0.3231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -0.0924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5487   -0.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -1.5236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3673   -1.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2223   -1.0904    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7208   -1.6380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9533   -1.7741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2581   -0.7327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144   -1.2636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5812    0.1224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0241    0.6829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8773    0.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9558   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1345   -2.0445    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  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  7 15  1  6  0  0  0
  5 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0303114

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1CCC2(O)C(C)(C)C3CC[C@@]2(C)C1C3

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11?,12?,14-,15?/m0/s1

> <INCHI_KEY>
GGHMUJBZYLPWFD-DUNKBJDJSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.731404307646002

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
3.5033453626666664

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.2907522675014106

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.21849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
patchoulol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303114
     RDKit          3D
Patchouli alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.2001    0.6939   -1.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.5329   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3878    1.8050   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126    1.7150    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    0.4518    0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    0.3728    2.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.3267   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9844    1.5551   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -0.1923    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7262   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -2.1081   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -2.0528    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.7390    0.8121 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2615   -0.8217    2.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323   -0.6071   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.4218   -1.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481    0.5722   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -0.0944   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623    1.6913   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    0.3434    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    2.5517    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    2.2029   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539    2.5890    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    1.8823    1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -0.5433    2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727    2.1541   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    1.2439   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2017    2.2362   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.6505    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -0.3275   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.0504    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8004   -0.7248   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -2.4147   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -2.8088   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -2.3628    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -2.8255    0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686   -1.4567    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -1.3722    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5295    0.1425    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -1.5567   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    0.6018   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -1.1084   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15  2  1  0
 13  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       3.313   0.156   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.973  -0.603   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.192  -0.172   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.024  -1.211   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.924  -2.844   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.686  -3.281   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.282  -2.035   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.212  -3.058   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.779  -3.312   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.482  -1.368   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.214  -2.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.085   0.228   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.045   1.275   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.638   1.666   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.651  -1.331   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.118  -3.816   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    2    8   15                                             
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10    6                                                       
CONECT   12   10    2   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    7                                                            
CONECT   16    5                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0303114
HETATM    1  C1  UNL     1       3.200   0.694  -1.297  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.163   0.533  -0.230  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.388   1.805  -0.058  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.213   1.715   0.837  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.551   0.452   0.839  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.211   0.373   2.094  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.621   0.327  -0.194  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.984   1.555  -0.926  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.942  -0.192   0.400  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.154  -0.726  -1.200  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.186  -2.108  -0.572  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.346  -2.053   0.680  1.00  0.00           C  
HETATM   13  C12 UNL     1       0.385  -0.739   0.812  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.262  -0.822   2.017  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.232  -0.607  -0.462  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.280  -0.422  -1.595  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.248   0.572  -0.894  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.054  -0.094  -2.073  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.162   1.691  -1.741  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.698   0.343   0.729  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.116   2.552   0.385  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.187   2.203  -1.073  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.454   2.589   0.653  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.587   1.882   1.893  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.343  -0.543   2.383  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.773   2.154  -0.382  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.508   1.244  -1.879  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.202   2.236  -1.211  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.300   0.651   1.061  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.651  -0.328  -0.428  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.804  -1.050   1.048  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.800  -0.725  -2.079  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.240  -2.415  -0.365  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.807  -2.809  -1.329  1.00  0.00           H  
HETATM   35  H19 UNL     1      -0.873  -2.363   1.589  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.466  -2.825   0.531  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.769  -1.457   2.809  1.00  0.00           H  
HETATM   38  H22 UNL     1       2.209  -1.372   1.775  1.00  0.00           H  
HETATM   39  H23 UNL     1       1.530   0.143   2.461  1.00  0.00           H  
HETATM   40  H24 UNL     1       1.809  -1.557  -0.542  1.00  0.00           H  
HETATM   41  H25 UNL     1       0.281   0.602  -2.016  1.00  0.00           H  
HETATM   42  H26 UNL     1       0.513  -1.108  -2.451  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   15   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    7   13
CONECT    6   25
CONECT    7    8    9   10
CONECT    8   26   27   28
CONECT    9   29   30   31
CONECT   10   11   16   32
CONECT   11   12   33   34
CONECT   12   13   35   36
CONECT   13   14   15
CONECT   14   37   38   39
CONECT   15   16   40
CONECT   16   41   42
END

HMDB0303114
     RDKit          3D
Patchouli alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
    3.2001    0.6939   -1.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1629    0.5329   -0.2297 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3878    1.8050   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126    1.7150    0.8370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5514    0.4518    0.8385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2112    0.3728    2.0936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6213    0.3267   -0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9844    1.5551   -0.9260 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9417   -0.1923    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.7262   -1.2005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1856   -2.1081   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -2.0528    0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3850   -0.7390    0.8121 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2615   -0.8217    2.0173 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2323   -0.6071   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.4218   -1.5949 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2481    0.5722   -0.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0540   -0.0944   -2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1623    1.6913   -1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6980    0.3434    0.7291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    2.5517    0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1871    2.2029   -1.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4539    2.5890    0.6532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5872    1.8823    1.8935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3433   -0.5433    2.3831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7727    2.1541   -0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    1.2439   -1.8788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2017    2.2362   -1.2108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3001    0.6505    1.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6513   -0.3275   -0.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8035   -1.0504    1.0476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8004   -0.7248   -2.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2398   -2.4147   -0.3647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8065   -2.8088   -1.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729   -2.3628    1.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663   -2.8255    0.5310 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7686   -1.4567    2.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2090   -1.3722    1.7749 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5295    0.1425    2.4609 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8086   -1.5567   -0.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2808    0.6018   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5127   -1.1084   -2.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 15  2  1  0
 13  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

(6S,8S)-2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

Traditional Name

patchoulol

CAS Registry Number

Not Available

SMILES

C[C@H]1CCC2(O)C(C)(C)C3CC[C@@]2(C)C1C3

InChI Identifier

InChI=1S/C15H26O/c1-10-5-8-15(16)13(2,3)11-6-7-14(15,4)12(10)9-11/h10-12,16H,5-9H2,1-4H3/t10-,11?,12?,14-,15?/m0/s1

InChI Key

GGHMUJBZYLPWFD-DUNKBJDJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Bisabolanes (C09705 )

Ontology

Exogenous (HMDB: HMDB0303114)

Food

Herb and spice

Spice

Ginger (FooDB: FOOD00206)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0303114)

Pesticide (HMDB: HMDB0303114)

Biological role

Anti bacterial (HMDB: HMDB0303114)
Anti plaque (HMDB: HMDB0303114)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	4.19	ALOGPS
logP	3.5	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	0.29	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	0	ChemAxon
Refractivity	66.22 m³·mol⁻¹	ChemAxon
Polarizability	26.73 Å³	ChemAxon
Number of Rings	3	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
AllCCS	[M+H]+	152.658	32859911
AllCCS	[M+H-H2O]+	148.945	32859911
AllCCS	[M+Na]+	157.104	32859911
AllCCS	[M+NH4]+	156.11	32859911
AllCCS	[M-H]-	162.047	32859911
AllCCS	[M+Na-2H]-	162.443	32859911
AllCCS	[M+HCOO]-	162.985	32859911
DeepCCS	[M+H]+	157.651	30932474
DeepCCS	[M-H]-	155.293	30932474
DeepCCS	[M-2H]-	189.084	30932474
DeepCCS	[M+Na]+	164.176	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	18.5555 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.35 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2475.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	609.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	220.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	300.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	467.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	880.3 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	850.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1434.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	474.8 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	1599.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	540.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	475.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	622.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.6 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 10V, Positive-QTOF	splash10-0ab9-0090000000-412e927ce25bb5d868dd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 20V, Positive-QTOF	splash10-0ab9-1190000000-343c2f5bd1e5abde6738	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 40V, Positive-QTOF	splash10-0a73-6910000000-4dbcc13dc2070a358139	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 10V, Negative-QTOF	splash10-00di-0090000000-a777693b0c27d8da066a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 20V, Negative-QTOF	splash10-00di-0090000000-f582c797c33e8f169006	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 40V, Negative-QTOF	splash10-0abi-2690000000-fe8049fa983431f60521	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 10V, Positive-QTOF	splash10-05fr-0090000000-a06fb2931f4f096f5b8f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 20V, Positive-QTOF	splash10-06di-0590000000-5f614a4037c22a2b2f28	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 40V, Positive-QTOF	splash10-0006-6950000000-af3c7f8b2d7b717917cd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Patchouli alcohol 40V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442384

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1040361

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Patchouli alcohol (HMDB0303114)

MOL for HMDB0303114 (Patchouli alcohol)

3D MOL for HMDB0303114 (Patchouli alcohol)

3D SDF for HMDB0303114 (Patchouli alcohol)

3D-SDF for HMDB0303114 (Patchouli alcohol)

PDB for HMDB0303114 (Patchouli alcohol)

3D PDB for HMDB0303114 (Patchouli alcohol)

SMILES for HMDB0303114 (Patchouli alcohol)

INCHI for HMDB0303114 (Patchouli alcohol)

Structure for HMDB0303114 (Patchouli alcohol)

3D Structure for HMDB0303114 (Patchouli alcohol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra