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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:32:27 UTC

Update Date

2022-03-07 03:17:37 UTC

HMDB ID

HMDB0059841

Secondary Accession Numbers

HMDB59841

Metabolite Identification

Common Name

Cubenol

Description

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

Structure

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

HMDB0059841
     RDKit          3D
Cubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.3509   -3.3502   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -2.0540    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.6900   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -0.3330    0.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2112   -0.0334   -0.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.9414   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -0.9049    1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.5534   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884    1.3915   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.3027   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6327    1.9998    0.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6665    3.0633   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223    0.6104   -0.1122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2182    0.3432   -1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.3322    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -1.0723    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -3.1036   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668   -3.9047   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -3.9696    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.3816   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -0.2720    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -0.1666   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -2.0077   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.3696    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -1.9228    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   -0.3501    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.3616   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -1.4158   -1.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0993    0.2891   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122    1.6434    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.5300   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    2.0883   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.3609   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    2.0233    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    2.9123    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358    4.0211    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    3.2185   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607    0.9873   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.4621   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    1.0736    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -1.4050    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452   -1.0898    2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  6
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 03071314322D          

 19 20  0  0  0  0            999 V2000
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  4  1  1  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  6  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  1  0  0  0
 12 17  1  6  0  0  0
 13 18  1  1  0  0  0
 14 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0059841

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@]2([H])C=C(C)CC[C@@]12O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(16)8-7-11(3)9-14(13)15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13+,14+,15-/m1/s1

> <INCHI_KEY>
COGPRPSWSKLKTF-CBBWQLFWSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.792263186545483

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-4a-ol

> <ALOGPS_LOGP>
3.76

> <JCHEM_LOGP>
3.6946274139999993

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.2067288542818434

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.2765

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,4aR,8aR)-1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059841
     RDKit          3D
Cubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.3509   -3.3502   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -2.0540    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.6900   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -0.3330    0.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2112   -0.0334   -0.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.9414   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -0.9049    1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.5534   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884    1.3915   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.3027   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6327    1.9998    0.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6665    3.0633   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223    0.6104   -0.1122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2182    0.3432   -1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.3322    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -1.0723    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -3.1036   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668   -3.9047   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -3.9696    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.3816   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -0.2720    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -0.1666   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -2.0077   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.3696    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -1.9228    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   -0.3501    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.3616   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -1.4158   -1.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0993    0.2891   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122    1.6434    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.5300   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    2.0883   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.3609   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    2.0233    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    2.9123    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358    4.0211    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    3.2185   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607    0.9873   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.4621   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    1.0736    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -1.4050    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452   -1.0898    2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  6
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 07-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-13         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335   3.080   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0       5.335  -1.540   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7    8   11                                                       
CONECT    8    7   15                                                       
CONECT    9   11   14                                                       
CONECT   10    1    2   13                                                  
CONECT   11    3    7    9                                                  
CONECT   12    4    5   15   17                                             
CONECT   13    6   10   14   18                                             
CONECT   14    9   13   15   19                                             
CONECT   15    8   12   14   16                                             
CONECT   16   15                                                            
CONECT   17   12                                                            
CONECT   18   13                                                            
CONECT   19   14                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0059841
HETATM    1  C1  UNL     1      -2.351  -3.350  -0.142  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.754  -2.054   0.247  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.508  -1.690  -0.048  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.025  -0.333   0.411  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.211  -0.033  -0.370  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.360  -0.941  -0.072  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.797  -0.905   1.359  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.507  -0.553  -0.994  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.688   1.392  -0.223  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.568   2.303  -0.684  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.633   2.000   0.175  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.667   3.063  -0.055  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.122   0.610  -0.112  1.00  0.00           C  
HETATM   14  O1  UNL     1      -1.218   0.343  -1.474  1.00  0.00           O  
HETATM   15  C14 UNL     1      -2.454   0.332   0.530  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.565  -1.072   1.018  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.331  -3.104  -0.647  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.767  -3.905  -0.875  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.625  -3.970   0.730  1.00  0.00           H  
HETATM   20  H4  UNL     1       0.103  -2.382  -0.604  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.075  -0.272   1.493  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.958  -0.167  -1.453  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.126  -2.008  -0.319  1.00  0.00           H  
HETATM   24  H8  UNL     1       3.769  -0.370   1.412  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.980  -1.923   1.775  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.070  -0.350   1.983  1.00  0.00           H  
HETATM   27  H11 UNL     1       3.079  -0.362  -1.995  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.211  -1.416  -1.109  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.099   0.289  -0.598  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.012   1.643   0.792  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.519   1.530  -0.954  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.356   2.088  -1.750  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.845   3.361  -0.612  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.307   2.023   1.234  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.610   2.912   0.467  1.00  0.00           H  
HETATM   36  H20 UNL     1      -1.236   4.021   0.319  1.00  0.00           H  
HETATM   37  H21 UNL     1      -1.798   3.219  -1.157  1.00  0.00           H  
HETATM   38  H22 UNL     1      -1.761   0.987  -1.963  1.00  0.00           H  
HETATM   39  H23 UNL     1      -3.238   0.462  -0.267  1.00  0.00           H  
HETATM   40  H24 UNL     1      -2.597   1.074   1.347  1.00  0.00           H  
HETATM   41  H25 UNL     1      -3.623  -1.405   1.118  1.00  0.00           H  
HETATM   42  H26 UNL     1      -2.145  -1.090   2.067  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   16
CONECT    3    4   20
CONECT    4    5   13   21
CONECT    5    6    9   22
CONECT    6    7    8   23
CONECT    7   24   25   26
CONECT    8   27   28   29
CONECT    9   10   30   31
CONECT   10   11   32   33
CONECT   11   12   13   34
CONECT   12   35   36   37
CONECT   13   14   15
CONECT   14   38
CONECT   15   16   39   40
CONECT   16   41   42
END

HMDB0059841
     RDKit          3D
Cubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
   -2.3509   -3.3502   -0.1420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7544   -2.0540    0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5083   -1.6900   -0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0251   -0.3330    0.4114 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2112   -0.0334   -0.3699 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3597   -0.9414   -0.0720 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7968   -0.9049    1.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5066   -0.5534   -0.9938 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6884    1.3915   -0.2231 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685    2.3027   -0.6841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6327    1.9998    0.1747 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6665    3.0633   -0.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1223    0.6104   -0.1122 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2182    0.3432   -1.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4540    0.3322    0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5649   -1.0723    1.0181 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3307   -3.1036   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7668   -3.9047   -0.8746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6246   -3.9696    0.7297 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1030   -2.3816   -0.6038 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0748   -0.2720    1.4929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -0.1666   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1264   -2.0077   -0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7686   -0.3696    1.4117 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9799   -1.9228    1.7754 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0698   -0.3501    1.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -0.3616   -1.9946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2108   -1.4158   -1.1091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0993    0.2891   -0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0122    1.6434    0.7919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5193    1.5300   -0.9544 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3560    2.0883   -1.7501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452    3.3609   -0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3073    2.0233    1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6096    2.9123    0.4672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2358    4.0211    0.3191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975    3.2185   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7607    0.9873   -1.9629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2378    0.4621   -0.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5969    1.0736    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6229   -1.4050    1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1452   -1.0898    2.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  5  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
 16  2  1  0
 13  4  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  1
  5 22  1  6
  6 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  1
 12 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Cubenol	MeSH

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

(1S,4R,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalen-4a-ol

Traditional Name

(1S,4R,4aR,8aR)-1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@]2([H])C=C(C)CC[C@@]12O

InChI Identifier

InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(16)8-7-11(3)9-14(13)15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13+,14+,15-/m1/s1

InChI Key

COGPRPSWSKLKTF-CBBWQLFWSA-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

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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
Water Solubility	0.064 g/L	ALOGPS
logP	3.76	ALOGPS
logP	3.69	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	-0.21	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	1	ChemAxon
Refractivity	69.28 m³·mol⁻¹	ChemAxon
Polarizability	27.79 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	154.359	31661259
DarkChem	[M-H]-	154.456	31661259
DeepCCS	[M-2H]-	194.165	30932474
DeepCCS	[M+Na]+	169.393	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.1	32859911
AllCCS	[M+NH4]+	156.2	32859911
AllCCS	[M+Na]+	157.2	32859911
AllCCS	[M-H]-	160.7	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.39 minutes	32390414
Predicted by Siyang on May 30, 2022	16.5508 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2437.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	501.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	196.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	221.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	782.6 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	762.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	79.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1304.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	483.1 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	1352.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	465.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	386.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	366.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	531.1 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	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cubenol	[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@]2([H])C=C(C)CC[C@@]12O	2150.5	Standard polar	33892256
Cubenol	[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@]2([H])C=C(C)CC[C@@]12O	1618.2	Standard non polar	33892256
Cubenol	[H][C@@]1(C)CC[C@@]([H])(C(C)C)[C@]2([H])C=C(C)CC[C@@]12O	1624.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cubenol,1TMS,isomer #1	CC1=C[C@H]2[C@H](C(C)C)CC[C@@H](C)[C@]2(O[Si](C)(C)C)CC1	1675.4	Semi standard non polar	33892256
Cubenol,1TBDMS,isomer #1	CC1=C[C@H]2[C@H](C(C)C)CC[C@@H](C)[C@]2(O[Si](C)(C)C(C)(C)C)CC1	1901.4	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 - Cubenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-2910000000-ebd7f4fd30bcde08385e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cubenol GC-MS (1 TMS) - 70eV, Positive	splash10-0fvr-3190000000-f83e568356ec58491bc1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cubenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cubenol 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 - Cubenol 10V, Positive-QTOF	splash10-0ab9-0090000000-406604020c501d35e982	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 20V, Positive-QTOF	splash10-0a4i-5980000000-2c28730cb04084655e96	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 40V, Positive-QTOF	splash10-0a4i-9500000000-90ba461d8573314d6c9a	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 10V, Negative-QTOF	splash10-00di-0090000000-349e104d07014abe41b7	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 20V, Negative-QTOF	splash10-00di-0090000000-ea2e986175b85dcbef8d	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 40V, Negative-QTOF	splash10-0a4i-0930000000-56d4b9d05344f8d1b41f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 10V, Positive-QTOF	splash10-00di-0490000000-9da1b8bcf0df5ff0c580	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 20V, Positive-QTOF	splash10-0ab9-7960000000-48cd9da92a8924bbe71c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 40V, Positive-QTOF	splash10-0006-9200000000-ceb885fcaa71b27c984c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cubenol 40V, Negative-QTOF	splash10-014i-0490000000-6a34466c183c53580199	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

KNApSAcK ID

Not Available

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

11770062

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Cubenol (HMDB0059841)

MOL for HMDB0059841 (Cubenol)

3D MOL for HMDB0059841 (Cubenol)

3D SDF for HMDB0059841 (Cubenol)

3D-SDF for HMDB0059841 (Cubenol)

PDB for HMDB0059841 (Cubenol)

3D PDB for HMDB0059841 (Cubenol)

SMILES for HMDB0059841 (Cubenol)

INCHI for HMDB0059841 (Cubenol)

Structure for HMDB0059841 (Cubenol)

3D Structure for HMDB0059841 (Cubenol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra