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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:16 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032698

Secondary Accession Numbers

HMDB32698

Metabolite Identification

Common Name

Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene

Description

Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene, also known as mestranol bicarbonate, belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group. Based on a literature review very few articles have been published on Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene.

Structure

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

HMDB0032698
     RDKit          3D
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene
 47 48  0  0  0  0  0  0  0  0999 V2000
   -0.4153   -4.3865    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -3.0077    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -2.6777   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272   -1.3992   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.4190   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908    0.9551   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0653   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    1.6969    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    1.2327    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129    1.1388   -0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.8555    1.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -0.2552    2.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.5376    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    1.1005   -2.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    1.3696   -2.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.7479    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.2319    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0549    0.3945   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -0.4158   -1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    1.4780   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    1.3323    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661    1.6432   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877   -2.0179    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.5482    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0963    2.4581    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    2.9269   -0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286    1.7283    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.0418    3.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504   -0.6650    2.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871   -1.0790    2.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898    0.7845    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038    1.1522   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -0.5303    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6018    0.1948   -3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    1.9725   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    2.4354   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6914    1.0446    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0323    0.5789    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703    2.2706    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.8070   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413    1.8236   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    2.5492   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.2249    1.1604 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
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M  END


  Mrv0541 05061306382D          

 23 24  0  0  0  0            999 V2000
    3.1922   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777   -2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3138   -3.7157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3343   -0.9185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1926   -1.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.3802   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7633   -0.0935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889   -4.0022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.9105   -0.6990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4408   -2.5950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0032698

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C(=O)OCC1(CO1)C1=C(OC(=O)C(C)C)C=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H24O5/c1-11(2)16(19)21-9-18(10-22-18)14-7-6-13(5)8-15(14)23-17(20)12(3)4/h6-8,11-12H,9-10H2,1-5H3

> <INCHI_KEY>
OLARKEMZPWGFJU-UHFFFAOYSA-N

> <FORMULA>
C18H24O5

> <MOLECULAR_WEIGHT>
320.3802

> <EXACT_MASS>
320.162373878

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
34.51356037864191

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2-{4-methyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl 2-methylpropanoate

> <ALOGPS_LOGP>
3.74

> <JCHEM_LOGP>
4.0197834053333334

> <ALOGPS_LOGS>
-4.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.253650410485524

> <JCHEM_POLAR_SURFACE_AREA>
65.13000000000001

> <JCHEM_REFRACTIVITY>
85.2361

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2-{4-methyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032698
     RDKit          3D
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene
 47 48  0  0  0  0  0  0  0  0999 V2000
   -0.4153   -4.3865    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -3.0077    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -2.6777   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272   -1.3992   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.4190   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908    0.9551   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0653   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    1.6969    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    1.2327    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129    1.1388   -0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.8555    1.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -0.2552    2.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.5376    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    1.1005   -2.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    1.3696   -2.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.7479    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.2319    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0549    0.3945   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -0.4158   -1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    1.4780   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    1.3323    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661    1.6432   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877   -2.0179    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.5482    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -4.6221    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -5.1541    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.4542   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.1955   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963    2.4581    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6018    0.1948   -3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    1.9725   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    2.4354   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6914    1.0446    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0323    0.5789    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703    2.2706    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.8070   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413    1.8236   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    2.5492   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.2249    1.1604 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
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 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  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       5.959  -1.715   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.625  -4.025   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.186  -6.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.723  -4.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.397  -8.273   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.860  -5.646   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -4.199   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.646  -6.559   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.624  -1.715   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.226  -2.752   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.625  -2.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.196  -5.756   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.870  -6.826   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.183  -3.932   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.173  -5.111   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.291  -1.715   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.679  -6.024   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.710  -2.485   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       3.291  -0.175   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -3.153  -7.471   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.958  -2.485   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -1.700  -1.305   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.689  -4.844   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    7   13                                                       
CONECT    7    6   14                                                       
CONECT    8   13   15                                                       
CONECT    9   18   21                                                       
CONECT   10   18   22                                                       
CONECT   11    1    2   16                                                  
CONECT   12    3    4   17                                                  
CONECT   13    5    6    8                                                  
CONECT   14    7   15   18                                                  
CONECT   15    8   14   23                                                  
CONECT   16   11   19   21                                                  
CONECT   17   12   20   23                                                  
CONECT   18    9   10   14   22                                             
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21    9   16                                                       
CONECT   22   10   18                                                       
CONECT   23   15   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0032698
HETATM    1  C1  UNL     1      -0.415  -4.386   1.023  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.239  -3.008   0.480  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.911  -2.678  -0.207  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.127  -1.399  -0.737  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.155  -0.419  -0.570  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.291   0.955  -1.096  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.765   2.065  -0.196  1.00  0.00           C  
HETATM    8  O1  UNL     1       1.751   1.697   0.727  1.00  0.00           O  
HETATM    9  C8  UNL     1       3.019   1.233   0.424  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.313   1.139  -0.796  1.00  0.00           O  
HETATM   11  C9  UNL     1       4.009   0.855   1.466  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.525  -0.255   2.352  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.326   0.538   0.790  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.570   1.100  -2.561  1.00  0.00           C  
HETATM   15  O3  UNL     1      -0.690   1.370  -2.035  1.00  0.00           O  
HETATM   16  C13 UNL     1      -0.995  -0.748   0.116  1.00  0.00           C  
HETATM   17  O4  UNL     1      -1.959   0.232   0.279  1.00  0.00           O  
HETATM   18  C14 UNL     1      -3.055   0.395  -0.557  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.152  -0.416  -1.514  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.997   1.478  -0.266  1.00  0.00           C  
HETATM   21  C16 UNL     1      -4.619   1.332   1.098  1.00  0.00           C  
HETATM   22  C17 UNL     1      -5.066   1.643  -1.299  1.00  0.00           C  
HETATM   23  C18 UNL     1      -1.188  -2.018   0.632  1.00  0.00           C  
HETATM   24  H1  UNL     1       0.188  -4.548   1.948  1.00  0.00           H  
HETATM   25  H2  UNL     1      -1.475  -4.622   1.215  1.00  0.00           H  
HETATM   26  H3  UNL     1      -0.058  -5.154   0.283  1.00  0.00           H  
HETATM   27  H4  UNL     1       1.670  -3.454  -0.334  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.028  -1.196  -1.264  1.00  0.00           H  
HETATM   29  H6  UNL     1      -0.096   2.458   0.389  1.00  0.00           H  
HETATM   30  H7  UNL     1       1.088   2.927  -0.839  1.00  0.00           H  
HETATM   31  H8  UNL     1       4.229   1.728   2.149  1.00  0.00           H  
HETATM   32  H9  UNL     1       3.432   0.042   3.420  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.550  -0.665   2.041  1.00  0.00           H  
HETATM   34  H11 UNL     1       4.287  -1.079   2.281  1.00  0.00           H  
HETATM   35  H12 UNL     1       6.190   0.784   1.427  1.00  0.00           H  
HETATM   36  H13 UNL     1       5.404   1.152  -0.133  1.00  0.00           H  
HETATM   37  H14 UNL     1       5.358  -0.530   0.440  1.00  0.00           H  
HETATM   38  H15 UNL     1       0.602   0.195  -3.195  1.00  0.00           H  
HETATM   39  H16 UNL     1       1.111   1.972  -2.953  1.00  0.00           H  
HETATM   40  H17 UNL     1      -3.400   2.435  -0.264  1.00  0.00           H  
HETATM   41  H18 UNL     1      -5.691   1.045   1.040  1.00  0.00           H  
HETATM   42  H19 UNL     1      -4.032   0.579   1.669  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.570   2.271   1.656  1.00  0.00           H  
HETATM   44  H21 UNL     1      -5.793   0.807  -1.304  1.00  0.00           H  
HETATM   45  H22 UNL     1      -4.641   1.824  -2.304  1.00  0.00           H  
HETATM   46  H23 UNL     1      -5.664   2.549  -1.007  1.00  0.00           H  
HETATM   47  H24 UNL     1      -2.103  -2.225   1.160  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   23
CONECT    3    4   27
CONECT    4    5    5   28
CONECT    5    6   16
CONECT    6    7   14   15
CONECT    7    8   29   30
CONECT    8    9
CONECT    9   10   10   11
CONECT   11   12   13   31
CONECT   12   32   33   34
CONECT   13   35   36   37
CONECT   14   15   38   39
CONECT   16   17   23   23
CONECT   17   18
CONECT   18   19   19   20
CONECT   20   21   22   40
CONECT   21   41   42   43
CONECT   22   44   45   46
CONECT   23   47
END

HMDB0032698
     RDKit          3D
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene
 47 48  0  0  0  0  0  0  0  0999 V2000
   -0.4153   -4.3865    1.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2386   -3.0077    0.4797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -2.6777   -0.2075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272   -1.3992   -0.7374 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1549   -0.4190   -0.5703 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2908    0.9551   -1.0961 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0653   -0.1956 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7511    1.6969    0.7267 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0194    1.2327    0.4244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3129    1.1388   -0.7957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0094    0.8555    1.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5247   -0.2552    2.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3265    0.5376    0.7899 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5700    1.1005   -2.5612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6904    1.3696   -2.0348 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947   -0.7479    0.1165 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9592    0.2319    0.2786 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0549    0.3945   -0.5572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1525   -0.4158   -1.5140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9971    1.4780   -0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6195    1.3323    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661    1.6432   -1.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877   -2.0179    0.6316 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1884   -4.5482    1.9478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4747   -4.6221    1.2151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0581   -5.1541    0.2827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6703   -3.4542   -0.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0285   -1.1955   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0963    2.4581    0.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0880    2.9269   -0.8394 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286    1.7283    2.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319    0.0418    3.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5504   -0.6650    2.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2871   -1.0790    2.2806 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1898    0.7845    1.4266 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4038    1.1522   -0.1331 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3576   -0.5303    0.4400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6018    0.1948   -3.1953 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1110    1.9725   -2.9530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4000    2.4354   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6914    1.0446    1.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0323    0.5789    1.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5703    2.2706    1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7927    0.8070   -1.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6413    1.8236   -2.3037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6639    2.5492   -1.0073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1028   -2.2249    1.1604 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  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 11 13  1  0
  6 14  1  0
 14 15  1  0
  5 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 16 23  2  0
 23  2  1  0
 15  6  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  7 29  1  0
  7 30  1  0
 11 31  1  0
 12 32  1  0
 12 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
 20 40  1  0
 21 41  1  0
 21 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Mestranol bicarbonate	HMDB
(2-{4-methyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl 2-methylpropanoic acid	HMDB

Chemical Formula

C₁₈H₂₄O₅

Average Molecular Weight

320.3802

Monoisotopic Molecular Weight

320.162373878

IUPAC Name

(2-{4-methyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl 2-methylpropanoate

Traditional Name

(2-{4-methyl-2-[(2-methylpropanoyl)oxy]phenyl}oxiran-2-yl)methyl 2-methylpropanoate

CAS Registry Number

22518-06-5

SMILES

CC(C)C(=O)OCC1(CO1)C1=C(OC(=O)C(C)C)C=C(C)C=C1

InChI Identifier

InChI=1S/C18H24O5/c1-11(2)16(19)21-9-18(10-22-18)14-7-6-13(5)8-15(14)23-17(20)12(3)4/h6-8,11-12H,9-10H2,1-5H3

InChI Key

OLARKEMZPWGFJU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenol esters. These are aromatic compounds containing a benzene ring substituted by a hydroxyl group and an ester group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenol esters

Sub Class

Not Available

Direct Parent

Phenol esters

Alternative Parents

Substituents

Phenol ester
Phenoxy compound
Toluene
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032698)

Cellular substructure

Membrane (HMDB: HMDB0032698)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032698)

Source

Endogenous

Endogenous (HMDB: HMDB0032698)

Exogenous

Food

Food (HMDB: HMDB0032698)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

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	0.017 g/L	ALOGPS
logP	3.74	ALOGPS
logP	4.02	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.13 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	85.24 m³·mol⁻¹	ChemAxon
Polarizability	34.51 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	175.496	31661259
DarkChem	[M-H]-	174.408	31661259
DeepCCS	[M+H]+	183.78	30932474
DeepCCS	[M-H]-	181.422	30932474
DeepCCS	[M-2H]-	215.308	30932474
DeepCCS	[M+Na]+	190.536	30932474
AllCCS	[M+H]+	174.7	32859911
AllCCS	[M+H-H2O]+	171.6	32859911
AllCCS	[M+NH4]+	177.5	32859911
AllCCS	[M+Na]+	178.3	32859911
AllCCS	[M-H]-	182.1	32859911
AllCCS	[M+Na-2H]-	182.3	32859911
AllCCS	[M+HCOO]-	182.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene	CC(C)C(=O)OCC1(CO1)C1=C(OC(=O)C(C)C)C=C(C)C=C1	3016.3	Standard polar	33892256
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene	CC(C)C(=O)OCC1(CO1)C1=C(OC(=O)C(C)C)C=C(C)C=C1	2148.5	Standard non polar	33892256
Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene	CC(C)C(=O)OCC1(CO1)C1=C(OC(=O)C(C)C)C=C(C)C=C1	2077.6	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 - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r5-8790000000-fd1cf3e58db53737df05	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 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 - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 10V, Positive-QTOF	splash10-00e9-6198000000-b15d9f9ff69bbb380648	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 20V, Positive-QTOF	splash10-0089-9371000000-aaa69914f493093f8c3b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 40V, Positive-QTOF	splash10-05fu-9000000000-b8d58cedfb180a6154ef	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 10V, Negative-QTOF	splash10-014l-7639000000-49f0dc7638ade490fbbd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 20V, Negative-QTOF	splash10-014r-9233000000-ae43c89dbc0ecc9d5296	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 40V, Negative-QTOF	splash10-05pc-9800000000-7ce0888ba4c036d53be5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 10V, Positive-QTOF	splash10-00e9-0269000000-7a87148e43d9b205c077	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 20V, Positive-QTOF	splash10-001i-2592000000-9ed48aba8e6aed99d47d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 40V, Positive-QTOF	splash10-0006-7941000000-b8d8ca8c98c849cbe6f0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 10V, Negative-QTOF	splash10-002k-4980000000-48a3460c98f1cc9ac422	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 20V, Negative-QTOF	splash10-0079-9310000000-6f5f745b93ba3cf8a8a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene 40V, Negative-QTOF	splash10-00ej-9510000000-3900ee635e8bde230521	2021-09-22	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

FDB010655

KNApSAcK ID

Not Available

Chemspider ID

9647499

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11472669

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 Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene (HMDB0032698)

MOL for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

3D MOL for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

3D SDF for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

3D-SDF for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

PDB for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

3D PDB for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

SMILES for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

INCHI for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

Structure for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

3D Structure for HMDB0032698 (Bis(2-methylpropanoyloxy)-9,10-epoxy-p-mentha-1,3,5-triene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra