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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:16:22 UTC

Update Date

2022-03-07 02:55:09 UTC

HMDB ID

HMDB0037031

Secondary Accession Numbers

HMDB37031

Metabolite Identification

Common Name

Epicubenol

Description

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

Structure

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

HMDB0037031
     RDKit          3D
Epicubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.8597    3.8726   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.3725   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    1.6194   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.1551   -0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -0.5472   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679   -0.2569    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    1.1939    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.0389    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -2.0297   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -2.5075    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -1.7972    0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673   -2.1758   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -0.2939    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445   -0.0456    1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    0.3934    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2111    1.8765    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    4.0039   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573    4.2006    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882    4.3929   -0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    2.1040   -1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.1847   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323   -0.2649   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228   -0.5375    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    1.5619   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792    1.3106    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    1.8463    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -0.7990    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -2.1194    0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216   -0.7569   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597   -2.6697   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.1127   -1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -3.5906    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -2.3992    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -2.0257    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -2.1925   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175   -3.2016   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -1.4899   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.6494    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    0.0436   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1094    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1831    2.3327    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    2.2972    0.0842 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  0
 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  0
  5 22  1  0
  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  0
 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 02241214362D          

 16 17  0  0  0  0            999 V2000
    1.0724    1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7861   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0710    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574    1.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3574   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    1.4436    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7861   -1.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0724   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574   -1.8562    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
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5 11  1  0  0  0  0
  5 15  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 10  2  0  0  0  0
  8  9  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037031

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)C2(O)CCC(C)=CC12

> <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

> <INCHI_KEY>
COGPRPSWSKLKTF-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.82814103329142

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
-0.20672885428184162

> <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>
1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037031
     RDKit          3D
Epicubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.8597    3.8726   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.3725   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    1.6194   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.1551   -0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -0.5472   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679   -0.2569    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    1.1939    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.0389    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -2.0297   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -2.5075    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -1.7972    0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673   -2.1758   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -0.2939    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445   -0.0456    1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    0.3934    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2111    1.8765    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    4.0039   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573    4.2006    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882    4.3929   -0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    2.1040   -1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.1847   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323   -0.2649   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228   -0.5375    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    1.5619   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792    1.3106    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    1.8463    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -0.7990    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -2.1194    0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216   -0.7569   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597   -2.6697   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.1127   -1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -3.5906    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -2.3992    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -2.0257    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -2.1925   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175   -3.2016   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -1.4899   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.6494    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    0.0436   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1094    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1831    2.3327    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    2.2972    0.0842 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  0
 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  0
  5 22  1  0
  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  0
 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                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.002   3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.002   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.334   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.334  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.002  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.334  -1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.999  -0.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.999   1.155   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.667   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.667  -1.155   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.667  -0.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.667   1.155   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.667   2.695   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.334  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.002  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.667  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   11   15                                                  
CONECT    6    7                                                            
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8   12                                                       
CONECT   10    7   11                                                       
CONECT   11    5   10   12                                                  
CONECT   12    2    9   11   13                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    5   14   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0037031
HETATM    1  C1  UNL     1       0.860   3.873  -0.370  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.049   2.373  -0.194  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.121   1.619  -0.749  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.186   0.155  -0.652  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.140  -0.547  -0.803  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.168  -0.257   0.209  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.574   1.194   0.295  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.450  -1.039   0.034  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.808  -2.030  -0.915  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.064  -2.507   0.310  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.233  -1.797   0.473  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.267  -2.176  -0.543  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.967  -0.294   0.522  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.345  -0.046   1.742  1.00  0.00           O  
HETATM   15  C14 UNL     1       2.310   0.393   0.612  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.211   1.876   0.544  1.00  0.00           C  
HETATM   17  H1  UNL     1       0.638   4.004  -1.449  1.00  0.00           H  
HETATM   18  H2  UNL     1       0.057   4.201   0.297  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.788   4.393  -0.055  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.717   2.104  -1.314  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.773  -0.185  -1.570  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.532  -0.265  -1.800  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.823  -0.537   1.245  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.921   1.562  -0.693  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.479   1.311   0.962  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.815   1.846   0.756  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.082  -0.799   0.922  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.216  -2.119   0.107  1.00  0.00           H  
HETATM   29  H13 UNL     1      -4.022  -0.757  -0.848  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.660  -2.670  -1.126  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.104  -2.113  -1.767  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.166  -3.591   0.127  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.644  -2.399   1.241  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.672  -2.026   1.488  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.292  -2.193  -0.085  1.00  0.00           H  
HETATM   36  H20 UNL     1       2.118  -3.202  -0.947  1.00  0.00           H  
HETATM   37  H21 UNL     1       2.320  -1.490  -1.402  1.00  0.00           H  
HETATM   38  H22 UNL     1       0.725  -0.649   2.421  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.951   0.044  -0.223  1.00  0.00           H  
HETATM   40  H24 UNL     1       2.834   0.109   1.548  1.00  0.00           H  
HETATM   41  H25 UNL     1       2.183   2.333   1.567  1.00  0.00           H  
HETATM   42  H26 UNL     1       3.153   2.297   0.084  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

HMDB0037031
     RDKit          3D
Epicubenol
 42 43  0  0  0  0  0  0  0  0999 V2000
    0.8597    3.8726   -0.3700 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0487    2.3725   -0.1944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1208    1.6194   -0.7493 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1860    0.1551   -0.6516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1397   -0.5472   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1679   -0.2569    0.2091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5741    1.1939    0.2951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4504   -1.0389    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8081   -2.0297   -0.9148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0635   -2.5075    0.3101 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2330   -1.7972    0.4729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2673   -2.1758   -0.5434 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9673   -0.2939    0.5218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3445   -0.0456    1.7421 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3100    0.3934    0.6122 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2111    1.8765    0.5436 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6384    4.0039   -1.4493 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0573    4.2006    0.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7882    4.3929   -0.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7166    2.1040   -1.3139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7729   -0.1847   -1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5323   -0.2649   -1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8228   -0.5375    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9215    1.5619   -0.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4792    1.3106    0.9623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8149    1.8463    0.7556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0825   -0.7990    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2159   -2.1194    0.1066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0216   -0.7569   -0.8482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6597   -2.6697   -1.1262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1044   -2.1127   -1.7669 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -3.5906    0.1270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6439   -2.3992    1.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6721   -2.0257    1.4879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2918   -2.1925   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1175   -3.2016   -0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3197   -1.4899   -1.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7253   -0.6494    2.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9506    0.0436   -0.2228 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8342    0.1094    1.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1831    2.3327    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1533    2.2972    0.0842 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  0
 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  0
  5 22  1  0
  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  0
 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
Epi-cubenol	HMDB
Cubenol	MeSH
Epicubenol	MeSH

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

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

Traditional Name

1-isopropyl-4,7-dimethyl-2,3,4,5,6,8a-hexahydro-1H-naphthalen-4a-ol

CAS Registry Number

19912-67-5

SMILES

CC(C)C1CCC(C)C2(O)CCC(C)=CC12

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

InChI Key

COGPRPSWSKLKTF-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

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

a sesquiterpenoid (CPD-12879 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037031)

Source

Exogenous

Exogenous (HMDB: HMDB0037031)

Food

Food (HMDB: HMDB0037031)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0037031)

Plant

Plant (HMDB: HMDB0037031)

Animal

Animal (HMDB: HMDB0037031)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037031)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037031)

Lipid metabolism pathway (HMDB: HMDB0037031)

Cellular process

Cell signaling (HMDB: HMDB0037031)

Biochemical process

Lipid transport (HMDB: HMDB0037031)

Role

Biological role

Energy source (HMDB: HMDB0037031)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037031)

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	9.13 mg/L @ 25 °C (est)	The Good Scents Company Information System
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	27.83 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]+	155.017	31661259
DarkChem	[M-H]-	148.764	31661259
DeepCCS	[M-2H]-	187.505	30932474
DeepCCS	[M+Na]+	163.114	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	148.6	32859911
AllCCS	[M+NH4]+	156.0	32859911
AllCCS	[M+Na]+	157.0	32859911
AllCCS	[M-H]-	160.7	32859911
AllCCS	[M+Na-2H]-	161.4	32859911
AllCCS	[M+HCOO]-	162.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epicubenol	CC(C)C1CCC(C)C2(O)CCC(C)=CC12	2166.9	Standard polar	33892256
Epicubenol	CC(C)C1CCC(C)C2(O)CCC(C)=CC12	1617.7	Standard non polar	33892256
Epicubenol	CC(C)C1CCC(C)C2(O)CCC(C)=CC12	1622.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epicubenol,1TMS,isomer #1	CC1=CC2C(C(C)C)CCC(C)C2(O[Si](C)(C)C)CC1	1724.7	Semi standard non polar	33892256
Epicubenol,1TBDMS,isomer #1	CC1=CC2C(C(C)C)CCC(C)C2(O[Si](C)(C)C(C)(C)C)CC1	1990.0	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 - Epicubenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aor-2910000000-111512c6fafa742b0fac	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epicubenol GC-MS (1 TMS) - 70eV, Positive	splash10-0fvr-3190000000-f83e568356ec58491bc1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epicubenol 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 - Epicubenol 10V, Positive-QTOF	splash10-0ab9-0290000000-7a35d479ddbd4829d3c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 20V, Positive-QTOF	splash10-0c00-3970000000-407486e1357e1d16db16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 40V, Positive-QTOF	splash10-0aor-9600000000-a24dc5d1649ce4073f2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 10V, Negative-QTOF	splash10-00di-0090000000-b0d0833ab0c8f145798e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 20V, Negative-QTOF	splash10-00di-0190000000-c25e09e4d431e8dc0445	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 40V, Negative-QTOF	splash10-0a4i-0920000000-0006e1a4c1269d380023	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 10V, Positive-QTOF	splash10-00di-0290000000-b06de3f5e5ed0416b4e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 20V, Positive-QTOF	splash10-03k9-3930000000-8960ad0fa5b9de2038b0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 40V, Positive-QTOF	splash10-052f-9100000000-28be6d1d486ec4131fcf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epicubenol 40V, Negative-QTOF	splash10-0kmi-0950000000-9acd7bb562666d7a8a7b	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016012

KNApSAcK ID

C00033734

Chemspider ID

453462

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

519857

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1443141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Cane DE, Ke N: Epicubenol synthase. Origin of the oxygen atom of a bacterial sesquiterpene alcohol. Bioorg Med Chem Lett. 2000 Jan 17;10(2):105-7. [PubMed:10673090 ]
Takei M, Umeyama A, Arihara S: Epicubenol and Ferruginol induce DC from human monocytes and differentiate IL-10-producing regulatory T cells in vitro. Biochem Biophys Res Commun. 2005 Nov 18;337(2):730-8. Epub 2005 Sep 26. [PubMed:16202980 ]
Catalan CA, de Heluani CS, Kotowicz C, Gedris TE, Herz W: A linear sesterterpene, two squalene derivatives and two peptide derivatives from Croton hieronymi. Phytochemistry. 2003 Sep;64(2):625-9. [PubMed:12943786 ]
Cole RA, Haber WA, Lawton RO, Setzer WN: Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica. Chem Biodivers. 2008 Jul;5(7):1327-34. doi: 10.1002/cbdv.200890120. [PubMed:18649320 ]
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 Epicubenol (HMDB0037031)

MOL for HMDB0037031 (Epicubenol)

3D MOL for HMDB0037031 (Epicubenol)

3D SDF for HMDB0037031 (Epicubenol)

3D-SDF for HMDB0037031 (Epicubenol)

PDB for HMDB0037031 (Epicubenol)

3D PDB for HMDB0037031 (Epicubenol)

SMILES for HMDB0037031 (Epicubenol)

INCHI for HMDB0037031 (Epicubenol)

Structure for HMDB0037031 (Epicubenol)

3D Structure for HMDB0037031 (Epicubenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra