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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:18 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036447

Secondary Accession Numbers

HMDB36447

Metabolite Identification

Common Name

Guaioxide

Description

Guaioxide, also known as liguloxide, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Guaioxide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, guaioxide has been detected, but not quantified in, herbs and spices. This could make guaioxide a potential biomarker for the consumption of these foods.

Structure

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

HMDB0036447
     RDKit          3D
Guaioxide
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.0230   -2.6179   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -1.7010   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102   -2.4168    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -1.9546    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020   -0.5329    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815    0.0999    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    0.5835    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.7492   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473    0.3844   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    1.6041    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222   -0.2234   -1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319    1.7930    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    3.0836    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    1.7241   -0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860    0.2630   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -0.4725    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277   -2.0083   -1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -3.2052   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8041   -3.2369   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.4329   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -2.4423    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -3.4994    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -2.2534   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -2.5777    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044   -0.4104    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    0.9113    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.5984    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    2.4816   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    1.8388    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    1.3306    0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.6114   -2.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.5425   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -0.9849   -1.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    1.6934    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260    3.2226    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    3.9106    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341    3.1538   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2355    2.1668   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.2627   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.0477   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.0613   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497   -0.7705    1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  9  5  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END


  Mrv0541 05061309092D          

 16 18  0  0  0  0            999 V2000
    1.0961   -0.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6890    3.2428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269    1.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8326    2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5007   -0.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7401    2.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2433    0.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7799    1.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7164    1.4589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7386    0.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5090    2.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5766    1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5398    2.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1015    1.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7748    2.4241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  5  1  0  0  0  0
 11  2  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036447

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(C)CCC3CC12OC3(C)C

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

> <INCHI_KEY>
GXMJXGUEPXEOGR-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.236524869143395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁵]dodecane

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
3.8687495126666667

> <ALOGPS_LOGS>
-5.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.211821570443764

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
66.6755

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.24e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁵]dodecane

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036447
     RDKit          3D
Guaioxide
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.0230   -2.6179   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -1.7010   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102   -2.4168    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -1.9546    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020   -0.5329    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815    0.0999    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    0.5835    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.7492   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473    0.3844   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    1.6041    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222   -0.2234   -1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319    1.7930    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    3.0836    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    1.7241   -0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860    0.2630   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -0.4725    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277   -2.0083   -1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -3.2052   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8041   -3.2369   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.4329   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -2.4423    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -3.4994    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -2.2534   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -2.5777    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044   -0.4104    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    0.9113    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.5984    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    2.4816   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    1.8388    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    1.3306    0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.6114   -2.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.5425   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -0.9849   -1.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    1.6934    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260    3.2226    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    3.9106    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341    3.1538   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2355    2.1668   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.2627   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.0477   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.0613   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497   -0.7705    1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  9  5  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.046  -0.360   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.153   6.053   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.077   3.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.154   5.211   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.668  -0.093   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.382   4.045   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.054   0.657   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.456   2.525   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.071   2.723   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.245   0.575   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.817   4.570   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.364   2.224   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.943   2.124   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.608   3.792   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.923   3.440   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.180   4.525   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5    7   10                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   13                                                       
CONECT    9   12   15                                                       
CONECT   10    1    5   13                                                  
CONECT   11    2    6   15                                                  
CONECT   12    7    9   14                                                  
CONECT   13    8   10   15                                                  
CONECT   14    3    4   12   16                                             
CONECT   15    9   11   13   16                                             
CONECT   16   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0036447
HETATM    1  C1  UNL     1      -2.023  -2.618  -0.896  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.845  -1.701  -0.539  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.010  -2.417   0.461  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.406  -1.955   0.554  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.602  -0.533   0.901  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.381   0.100   1.578  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.387   0.584   0.371  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.483   0.749  -0.667  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.747   0.384  -0.287  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.549   1.604   0.187  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.522  -0.223  -1.412  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.232   1.793   0.658  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.471   3.084   0.471  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.262   1.724  -0.460  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.386   0.263  -0.831  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.454  -0.472   0.093  1.00  0.00           C  
HETATM   17  H1  UNL     1      -2.928  -2.008  -1.160  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.311  -3.205  -0.007  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.804  -3.237  -1.779  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.291  -1.433  -1.448  1.00  0.00           H  
HETATM   21  H5  UNL     1      -0.547  -2.442   1.431  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.032  -3.499   0.137  1.00  0.00           H  
HETATM   23  H7  UNL     1       1.917  -2.253  -0.393  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.899  -2.578   1.348  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.504  -0.410   1.542  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.769   0.911   2.209  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.162  -0.598   2.208  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.359   2.482  -0.447  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.299   1.839   1.234  1.00  0.00           H  
HETATM   30  H14 UNL     1       3.626   1.331   0.125  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.757   0.611  -2.131  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.508  -0.543  -1.015  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.001  -0.985  -1.988  1.00  0.00           H  
HETATM   34  H18 UNL     1      -1.671   1.693   1.653  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.326   3.223   1.215  1.00  0.00           H  
HETATM   36  H20 UNL     1      -1.203   3.911   0.638  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.134   3.154  -0.574  1.00  0.00           H  
HETATM   38  H22 UNL     1      -3.235   2.167  -0.147  1.00  0.00           H  
HETATM   39  H23 UNL     1      -1.847   2.263  -1.346  1.00  0.00           H  
HETATM   40  H24 UNL     1      -3.442  -0.048  -0.633  1.00  0.00           H  
HETATM   41  H25 UNL     1      -2.094   0.061  -1.876  1.00  0.00           H  
HETATM   42  H26 UNL     1      -1.950  -0.770   1.024  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   16   20
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6    9   25
CONECT    6    7   26   27
CONECT    7    8   12   16
CONECT    8    9
CONECT    9   10   11
CONECT   10   28   29   30
CONECT   11   31   32   33
CONECT   12   13   14   34
CONECT   13   35   36   37
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   42
END

HMDB0036447
     RDKit          3D
Guaioxide
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.0230   -2.6179   -0.8962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8449   -1.7010   -0.5393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0102   -2.4168    0.4612 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4064   -1.9546    0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6020   -0.5329    0.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3815    0.0999    1.5779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3867    0.5835    0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4828    0.7492   -0.6671 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7473    0.3844   -0.2874 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5495    1.6041    0.1867 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5222   -0.2234   -1.4124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2319    1.7930    0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4708    3.0836    0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2619    1.7241   -0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860    0.2630   -0.8307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4542   -0.4725    0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9277   -2.0083   -1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3108   -3.2052   -0.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8041   -3.2369   -1.7794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2910   -1.4329   -1.4476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5471   -2.4423    1.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0319   -3.4994    0.1367 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9168   -2.2534   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8987   -2.5777    1.3479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5044   -0.4104    1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7688    0.9113    2.2090 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1620   -0.5984    2.2076 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3593    2.4816   -0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2986    1.8388    1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6263    1.3306    0.1247 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7572    0.6114   -2.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5077   -0.5425   -1.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0015   -0.9849   -1.9884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6712    1.6934    1.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3260    3.2226    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2034    3.9106    0.6381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1341    3.1538   -0.5741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2355    2.1668   -0.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8473    2.2627   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4416   -0.0477   -0.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0938    0.0613   -1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9497   -0.7705    1.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  7 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
  9  5  1  0
 16  7  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
 10 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Liguloxide	HMDB

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁵]dodecane

Traditional Name

2,6,10,10-tetramethyl-11-oxatricyclo[7.2.1.0¹,⁵]dodecane

CAS Registry Number

20149-50-2

SMILES

CC1CCC2C(C)CCC3CC12OC3(C)C

InChI Identifier

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

InChI Key

GXMJXGUEPXEOGR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036447)

Cellular substructure

Extracellular (HMDB: HMDB0036447)
Membrane (HMDB: HMDB0036447)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036447)

Source

Endogenous

Endogenous (HMDB: HMDB0036447)

Plant

Plant (HMDB: HMDB0036447)

Exogenous

Food

Food (HMDB: HMDB0036447)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036447)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036447)

Nutrient

Nutrient (HMDB: HMDB0036447)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036447)

Emulsifier (HMDB: HMDB0036447)

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	0.00042 g/L	ALOGPS
logP	4	ALOGPS
logP	3.87	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.68 m³·mol⁻¹	ChemAxon
Polarizability	27.24 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	152.329	31661259
DarkChem	[M-H]-	150.168	31661259
DeepCCS	[M-2H]-	188.928	30932474
DeepCCS	[M+Na]+	163.729	30932474
AllCCS	[M+H]+	152.5	32859911
AllCCS	[M+H-H2O]+	148.7	32859911
AllCCS	[M+NH4]+	156.0	32859911
AllCCS	[M+Na]+	157.0	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	163.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Guaioxide	CC1CCC2C(C)CCC3CC12OC3(C)C	1773.3	Standard polar	33892256
Guaioxide	CC1CCC2C(C)CCC3CC12OC3(C)C	1508.0	Standard non polar	33892256
Guaioxide	CC1CCC2C(C)CCC3CC12OC3(C)C	1508.0	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 - Guaioxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0933-2910000000-4fd554c3291bdf3324c8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Guaioxide 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 - Guaioxide 10V, Negative-QTOF	splash10-00di-0090000000-d0d6326e64dda742b0e0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 20V, Negative-QTOF	splash10-00di-0090000000-77662e9fb2e5b52eb395	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 40V, Negative-QTOF	splash10-0a6u-3930000000-2d5e3bbb0fe5200eef2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 40V, Negative-QTOF	splash10-014i-0090000000-a050bdb2c1cc57a08a12	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 10V, Positive-QTOF	splash10-00di-0090000000-046b1e71c341e9706b90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 20V, Positive-QTOF	splash10-00di-1890000000-773a81a0e4ef4455e2fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 40V, Positive-QTOF	splash10-052f-9410000000-3fda021f6fd6e04c14d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 10V, Positive-QTOF	splash10-00di-0090000000-e53c1eb3585d1d6c5666	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 20V, Positive-QTOF	splash10-00di-0190000000-4b4afeadfdd7f8ae4980	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Guaioxide 40V, Positive-QTOF	splash10-08ml-3930000000-e43fc46d929412b623dc	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB015334

KNApSAcK ID

C00020365

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

12302135

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Guaioxide (HMDB0036447)

MOL for HMDB0036447 (Guaioxide)

3D MOL for HMDB0036447 (Guaioxide)

3D SDF for HMDB0036447 (Guaioxide)

3D-SDF for HMDB0036447 (Guaioxide)

PDB for HMDB0036447 (Guaioxide)

3D PDB for HMDB0036447 (Guaioxide)

SMILES for HMDB0036447 (Guaioxide)

INCHI for HMDB0036447 (Guaioxide)

Structure for HMDB0036447 (Guaioxide)

3D Structure for HMDB0036447 (Guaioxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra