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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:54:00 UTC

Update Date

2022-03-07 02:55:02 UTC

HMDB ID

HMDB0036730

Secondary Accession Numbers

HMDB36730

Metabolite Identification

Common Name

Tricyclohumuladiol

Description

Tricyclohumuladiol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Tricyclohumuladiol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0036730
     RDKit          3D
Tricyclohumuladiol
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.7443   -0.3815   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -0.4660    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.4041    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745    0.9174    1.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.8601    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.5654    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -1.1032   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818   -2.5289   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -1.2859   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3158   -1.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.6703    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0053   -1.0957    1.8223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.8242    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5199    1.4419   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493    1.8000   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    2.1120   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    3.0471    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.3152   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.5275   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845   -1.2261   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -2.3638    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.4831    2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973   -0.9453    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642    1.6823    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.8983    2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1242    1.0522    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1893    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -0.9838   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -3.2484   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -2.9309    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.3472   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2067   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.6178   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.0379    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -0.2932    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    1.2326    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681    1.2001    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.8836   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    2.4181   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334    1.3587   -2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    2.3514   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    3.0591   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5169    3.3390    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  6  2  1  0
  9  7  1  0
 15  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
M  END


  Mrv0541 05061309182D          

 17 19  0  0  0  0            999 V2000
    3.5273    2.7723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3631    2.8491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0193    1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5849    0.4018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3319   -0.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1551   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4505    1.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6820    2.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4631    1.7392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8300    1.0644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.3723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2863    1.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068    2.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8426    1.1956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7757    0.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0069    0.1075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1402   -0.4989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036730

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CC1C1C(CC1(C)C)C(C)(O)CCC2O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-13(2)7-10-12(13)9-8-14(9,3)11(16)5-6-15(10,4)17/h9-12,16-17H,5-8H2,1-4H3

> <INCHI_KEY>
USFOCJBPTUMHRF-UHFFFAOYSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.3657

> <EXACT_MASS>
238.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.109040378993335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,8,11,11-tetramethyltricyclo[7.2.0.0²,⁴]undecane-5,8-diol

> <ALOGPS_LOGP>
2.18

> <JCHEM_LOGP>
1.9607193756666659

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.04514562177286

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.433486168951347

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8972122594836858

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
68.042

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,8,11,11-tetramethyltricyclo[7.2.0.0²,⁴]undecane-5,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036730
     RDKit          3D
Tricyclohumuladiol
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.7443   -0.3815   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -0.4660    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.4041    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745    0.9174    1.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.8601    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.5654    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -1.1032   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818   -2.5289   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -1.2859   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3158   -1.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.6703    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0053   -1.0957    1.8223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.8242    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5199    1.4419   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493    1.8000   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    2.1120   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    3.0471    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.3152   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.5275   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845   -1.2261   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -2.3638    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.4831    2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973   -0.9453    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642    1.6823    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.8983    2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1242    1.0522    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1893    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -0.9838   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -3.2484   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -2.9309    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.3472   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2067   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.6178   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.0379    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -0.2932    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    1.2326    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681    1.2001    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.8836   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    2.4181   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334    1.3587   -2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    2.3514   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    3.0591   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5169    3.3390    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  6  2  1  0
  9  7  1  0
 15  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  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       6.584   5.175   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.411   5.318   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.036   2.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.692   0.750   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.486  -0.463   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.023  -0.565   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.441   3.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.273   3.742   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.731   3.247   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.283   1.987   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.471   0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.268   3.145   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.426   4.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.573   2.232   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.181   0.450   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.013   0.201   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.862  -0.931   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7   10   13                                                       
CONECT    8    9   14                                                       
CONECT    9    8   12   14                                                  
CONECT   10    7   12   15                                                  
CONECT   11    5   14   16                                                  
CONECT   12    9   10   13                                                  
CONECT   13    1    2    7   12                                             
CONECT   14    3    8    9   11                                             
CONECT   15    4    6   10   17                                             
CONECT   16   11                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0036730
HETATM    1  C1  UNL     1      -2.744  -0.381  -0.728  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.025  -0.466   0.541  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.789  -1.404   1.492  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.875   0.917   1.191  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.402   0.860   0.940  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.534  -0.565   0.592  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.155  -1.103  -0.578  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.782  -2.529  -0.400  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.586  -1.286  -0.554  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.374  -1.316  -1.879  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.362  -0.670   0.546  1.00  0.00           C  
HETATM   12  O1  UNL     1       2.005  -1.096   1.822  1.00  0.00           O  
HETATM   13  C12 UNL     1       2.417   0.824   0.428  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.520   1.442  -0.564  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.149   1.800  -0.055  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.683   2.112  -1.258  1.00  0.00           C  
HETATM   17  O2  UNL     1       0.305   3.047   0.611  1.00  0.00           O  
HETATM   18  H1  UNL     1      -2.202  -0.315  -1.660  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.419   0.528  -0.699  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.485  -1.226  -0.870  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.921  -2.364   0.988  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.271  -1.483   2.461  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.797  -0.945   1.598  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.464   1.682   0.698  1.00  0.00           H  
HETATM   25  H8  UNL     1      -2.181   0.898   2.279  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.124   1.052   1.931  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.302  -1.189   1.516  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.292  -0.984  -1.609  1.00  0.00           H  
HETATM   29  H12 UNL     1       0.634  -3.248  -1.200  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.745  -2.931   0.638  1.00  0.00           H  
HETATM   31  H14 UNL     1       2.831  -2.347  -1.936  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.698  -1.207  -2.732  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.210  -0.618  -1.875  1.00  0.00           H  
HETATM   34  H17 UNL     1       3.430  -1.038   0.439  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.091  -0.293   2.415  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.159   1.233   1.436  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.468   1.200   0.249  1.00  0.00           H  
HETATM   38  H21 UNL     1       1.375   0.884  -1.510  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.983   2.418  -0.905  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.533   1.359  -2.063  1.00  0.00           H  
HETATM   41  H24 UNL     1      -1.728   2.351  -1.071  1.00  0.00           H  
HETATM   42  H25 UNL     1      -0.240   3.059  -1.698  1.00  0.00           H  
HETATM   43  H26 UNL     1      -0.517   3.339   1.036  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    6
CONECT    3   21   22   23
CONECT    4    5   24   25
CONECT    5    6   15   26
CONECT    6    7   27
CONECT    7    8    9   28
CONECT    8    9   29   30
CONECT    9   10   11
CONECT   10   31   32   33
CONECT   11   12   13   34
CONECT   12   35
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   17
CONECT   16   40   41   42
CONECT   17   43
END

HMDB0036730
     RDKit          3D
Tricyclohumuladiol
 43 45  0  0  0  0  0  0  0  0999 V2000
   -2.7443   -0.3815   -0.7284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0253   -0.4660    0.5407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7892   -1.4041    1.4919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8745    0.9174    1.1907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4019    0.8601    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5338   -0.5654    0.5922 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1550   -1.1032   -0.5775 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7818   -2.5289   -0.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5860   -1.2859   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3736   -1.3158   -1.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -0.6703    0.5460 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0053   -1.0957    1.8223 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167    0.8242    0.4282 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5199    1.4419   -0.5643 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1493    1.8000   -0.0553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6832    2.1120   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3053    3.0471    0.6109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2020   -0.3152   -1.6605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4187    0.5275   -0.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4845   -1.2261   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9208   -2.3638    0.9882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2711   -1.4831    2.4613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7973   -0.9453    1.5981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4642    1.6823    0.6976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.8983    2.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1242    1.0522    1.9307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -1.1893    1.5163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2921   -0.9838   -1.6095 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6343   -3.2484   -1.1997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7448   -2.9309    0.6376 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.3472   -1.9364 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6984   -1.2067   -2.7321 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2101   -0.6178   -1.8753 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4302   -1.0379    0.4386 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0913   -0.2932    2.4151 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1594    1.2326    1.4361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4681    1.2001    0.2485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3745    0.8836   -1.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9826    2.4181   -0.9052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5334    1.3587   -2.0629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7277    2.3514   -1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2401    3.0591   -1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5169    3.3390    1.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  6  2  1  0
  9  7  1  0
 15  5  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₂

Average Molecular Weight

238.3657

Monoisotopic Molecular Weight

238.193280076

IUPAC Name

4,8,11,11-tetramethyltricyclo[7.2.0.0²,⁴]undecane-5,8-diol

Traditional Name

4,8,11,11-tetramethyltricyclo[7.2.0.0²,⁴]undecane-5,8-diol

CAS Registry Number

21446-02-6

SMILES

CC12CC1C1C(CC1(C)C)C(C)(O)CCC2O

InChI Identifier

InChI=1S/C15H26O2/c1-13(2)7-10-12(13)9-8-14(9,3)11(16)5-6-15(10,4)17/h9-12,16-17H,5-8H2,1-4H3

InChI Key

USFOCJBPTUMHRF-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

Caryophyllane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036730)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036730)

Source

Endogenous

Endogenous (HMDB: HMDB0036730)

Animal

Animal (HMDB: HMDB0036730)

Exogenous

Food

Food (HMDB: HMDB0036730)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036730)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036730)

Cellular process

Cell signaling (HMDB: HMDB0036730)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036730)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036730)

Nutrient

Nutrient (HMDB: HMDB0036730)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036730)

Emulsifier (HMDB: HMDB0036730)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	207 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.31 g/L	ALOGPS
logP	2.18	ALOGPS
logP	1.96	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	14.43	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.04 m³·mol⁻¹	ChemAxon
Polarizability	28.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	157.812	31661259
DarkChem	[M-H]-	151.105	31661259
DeepCCS	[M-2H]-	190.56	30932474
DeepCCS	[M+Na]+	165.575	30932474
AllCCS	[M+H]+	156.3	32859911
AllCCS	[M+H-H2O]+	152.7	32859911
AllCCS	[M+NH4]+	159.6	32859911
AllCCS	[M+Na]+	160.5	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	164.6	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Tricyclohumuladiol	CC12CC1C1C(CC1(C)C)C(C)(O)CCC2O	2614.3	Standard polar	33892256
Tricyclohumuladiol	CC12CC1C1C(CC1(C)C)C(C)(O)CCC2O	1782.6	Standard non polar	33892256
Tricyclohumuladiol	CC12CC1C1C(CC1(C)C)C(C)(O)CCC2O	1749.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Tricyclohumuladiol,1TMS,isomer #1	CC1(C)CC2C1C1CC1(C)C(O)CCC2(C)O[Si](C)(C)C	1925.8	Semi standard non polar	33892256
Tricyclohumuladiol,1TMS,isomer #2	CC1(C)CC2C1C1CC1(C)C(O[Si](C)(C)C)CCC2(C)O	1916.0	Semi standard non polar	33892256
Tricyclohumuladiol,2TMS,isomer #1	CC1(C)CC2C1C1CC1(C)C(O[Si](C)(C)C)CCC2(C)O[Si](C)(C)C	1897.5	Semi standard non polar	33892256
Tricyclohumuladiol,1TBDMS,isomer #1	CC1(C)CC2C1C1CC1(C)C(O)CCC2(C)O[Si](C)(C)C(C)(C)C	2165.6	Semi standard non polar	33892256
Tricyclohumuladiol,1TBDMS,isomer #2	CC1(C)CC2C1C1CC1(C)C(O[Si](C)(C)C(C)(C)C)CCC2(C)O	2137.8	Semi standard non polar	33892256
Tricyclohumuladiol,2TBDMS,isomer #1	CC1(C)CC2C1C1CC1(C)C(O[Si](C)(C)C(C)(C)C)CCC2(C)O[Si](C)(C)C(C)(C)C	2338.7	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 - Tricyclohumuladiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zml-6930000000-3b92b94fdced0668e29b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tricyclohumuladiol GC-MS (2 TMS) - 70eV, Positive	splash10-0gb9-8679000000-d5b5a86790657607f5ff	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tricyclohumuladiol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Tricyclohumuladiol 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 - Tricyclohumuladiol 10V, Positive-QTOF	splash10-00dr-0090000000-9a77f6940c6e9d0cebbd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 20V, Positive-QTOF	splash10-0fk9-0190000000-f641da1979be495abad8	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 40V, Positive-QTOF	splash10-0zg0-8950000000-0e3f77b9c892ef0372a6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 10V, Negative-QTOF	splash10-000i-0090000000-a22b200767587e569bf7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 20V, Negative-QTOF	splash10-00kr-0090000000-77f3b42045e6ed999e3d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 40V, Negative-QTOF	splash10-000f-4920000000-a055df22993421e8a84a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 10V, Negative-QTOF	splash10-000i-0090000000-e665f494a7390ebf108d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 20V, Negative-QTOF	splash10-000i-0090000000-e665f494a7390ebf108d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 40V, Negative-QTOF	splash10-000i-0090000000-887792c196621dfe59c8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 10V, Positive-QTOF	splash10-000i-2290000000-3f501127e37d09377794	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 20V, Positive-QTOF	splash10-0a5i-9420000000-a65a84c1dcd1ed5d248c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Tricyclohumuladiol 40V, Positive-QTOF	splash10-0a4r-9000000000-1080627752a334918263	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB015667

KNApSAcK ID

C00022001

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73200635

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Tricyclohumuladiol (HMDB0036730)

MOL for HMDB0036730 (Tricyclohumuladiol)

3D MOL for HMDB0036730 (Tricyclohumuladiol)

3D SDF for HMDB0036730 (Tricyclohumuladiol)

3D-SDF for HMDB0036730 (Tricyclohumuladiol)

PDB for HMDB0036730 (Tricyclohumuladiol)

3D PDB for HMDB0036730 (Tricyclohumuladiol)

SMILES for HMDB0036730 (Tricyclohumuladiol)

INCHI for HMDB0036730 (Tricyclohumuladiol)

Structure for HMDB0036730 (Tricyclohumuladiol)

3D Structure for HMDB0036730 (Tricyclohumuladiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra