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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:02:53 UTC

Update Date

2022-03-07 02:53:40 UTC

HMDB ID

HMDB0033333

Secondary Accession Numbers

HMDB33333

Metabolite Identification

Common Name

2,3-Epoxysesamone

Description

2,3-Epoxysesamone belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position. Based on a literature review a significant number of articles have been published on 2,3-Epoxysesamone.

Structure

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

HMDB0033333
     RDKit          3D
2,3-Epoxysesamone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2842    1.6031   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130    0.3367   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.9281    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220    0.2827   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451   -0.9829   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.8002   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -0.5008    1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -1.7460    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -1.7169    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -2.6921    1.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.5535    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -0.2680    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905   -1.1125    2.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.8626    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    1.6810   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254    1.4087   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    2.2445   -1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571    0.2808   -0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7961   -0.0975   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056    0.1833   -2.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199    1.4588   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    2.4627   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.7018    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -1.6931   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.6941    0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023   -1.2977    1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.2125   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.1246   -2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320   -1.8201   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -2.6381    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0831   -0.8683    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    1.0737    1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641    2.5499   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426    2.1918   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  8  6  1  0
 18 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END

  Mrv0541 05061307042D          

 20 22  0  0  0  0            999 V2000
    0.1914    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.5079    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
    4.2868    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    3.7934    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    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
    2.1434    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    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  7  1  1  0  0  0  0
  7  2  1  0  0  0  0
  7  5  2  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 19 13  2  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033333

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3

> <INCHI_KEY>
TWESJUCJKWFWQV-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.334410420928975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

> <ALOGPS_LOGP>
2.45

> <JCHEM_LOGP>
3.286870548333333

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.248150665461441

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.490848770938264

> <JCHEM_PKA_STRONGEST_BASIC>
-4.34630274573094

> <JCHEM_POLAR_SURFACE_AREA>
87.13

> <JCHEM_REFRACTIVITY>
72.0792

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7aH-naphtho[2,3-b]oxirene-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033333
     RDKit          3D
2,3-Epoxysesamone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2842    1.6031   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130    0.3367   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.9281    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220    0.2827   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451   -0.9829   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.8002   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -0.5008    1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -1.7460    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -1.7169    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -2.6921    1.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.5535    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -0.2680    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905   -1.1125    2.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.8626    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    1.6810   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254    1.4087   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    2.2445   -1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571    0.2808   -0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7961   -0.0975   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056    0.1833   -2.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199    1.4588   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    2.4627   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.7018    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -1.6931   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.6941    0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023   -1.2977    1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.2125   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.1246   -2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320   -1.8201   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -2.6381    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0831   -0.8683    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    1.0737    1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641    2.5499   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426    2.1918   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  8  6  1  0
 18 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  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       0.357   7.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   8.415   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   5.747   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.897   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.668   5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001   5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    7                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    6    7                                                       
CONECT    6    5   15                                                       
CONECT    7    1    2    5                                                  
CONECT    8    3   10   16                                                  
CONECT    9    4   11   17                                                  
CONECT   10    8   11   12                                                  
CONECT   11    9   10   13                                                  
CONECT   12   10   14   18                                                  
CONECT   13   11   15   19                                                  
CONECT   14   12   15   20                                                  
CONECT   15    6   13   14   20                                             
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0033333
HETATM    1  C1  UNL     1      -4.284   1.603  -0.137  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.513   0.337  -0.247  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.069  -0.928   0.312  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.322   0.283  -0.836  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.545  -0.983  -0.949  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.221  -0.800  -0.238  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.348  -0.501   1.103  1.00  0.00           O  
HETATM    8  C7  UNL     1       0.293  -1.746   0.606  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.731  -1.717   0.909  1.00  0.00           C  
HETATM   10  O2  UNL     1       2.335  -2.692   1.475  1.00  0.00           O  
HETATM   11  C9  UNL     1       2.542  -0.554   0.570  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.737  -0.268   1.198  1.00  0.00           C  
HETATM   13  O3  UNL     1       4.191  -1.112   2.199  1.00  0.00           O  
HETATM   14  C11 UNL     1       4.409   0.863   0.776  1.00  0.00           C  
HETATM   15  C12 UNL     1       3.938   1.681  -0.215  1.00  0.00           C  
HETATM   16  C13 UNL     1       2.725   1.409  -0.867  1.00  0.00           C  
HETATM   17  O4  UNL     1       2.267   2.245  -1.861  1.00  0.00           O  
HETATM   18  C14 UNL     1       2.057   0.281  -0.446  1.00  0.00           C  
HETATM   19  C15 UNL     1       0.796  -0.098  -1.060  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.606   0.183  -2.277  1.00  0.00           O  
HETATM   21  H1  UNL     1      -5.220   1.459  -0.729  1.00  0.00           H  
HETATM   22  H2  UNL     1      -3.690   2.463  -0.467  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.610   1.702   0.927  1.00  0.00           H  
HETATM   24  H4  UNL     1      -4.213  -1.693  -0.463  1.00  0.00           H  
HETATM   25  H5  UNL     1      -4.977  -0.694   0.895  1.00  0.00           H  
HETATM   26  H6  UNL     1      -3.302  -1.298   1.044  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.934   1.212  -1.236  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.360  -1.125  -2.052  1.00  0.00           H  
HETATM   29  H9  UNL     1      -2.132  -1.820  -0.543  1.00  0.00           H  
HETATM   30  H10 UNL     1      -0.236  -2.638   0.967  1.00  0.00           H  
HETATM   31  H11 UNL     1       5.083  -0.868   2.644  1.00  0.00           H  
HETATM   32  H12 UNL     1       5.359   1.074   1.289  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.464   2.550  -0.533  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.443   2.192  -2.388  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7    8   19
CONECT    7    8
CONECT    8    9   30
CONECT    9   10   10   11
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   31
CONECT   14   15   15   32
CONECT   15   16   33
CONECT   16   17   18   18
CONECT   17   34
CONECT   18   19
CONECT   19   20   20
END

HMDB0033333
     RDKit          3D
2,3-Epoxysesamone
 34 36  0  0  0  0  0  0  0  0999 V2000
   -4.2842    1.6031   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5130    0.3367   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0692   -0.9281    0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3220    0.2827   -0.8358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5451   -0.9829   -0.9487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2215   -0.8002   -0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3476   -0.5008    1.1025 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2933   -1.7460    0.6060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7310   -1.7169    0.9088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3353   -2.6921    1.4750 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5423   -0.5535    0.5698 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7367   -0.2680    1.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1905   -1.1125    2.1991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4087    0.8626    0.7762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    1.6810   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7254    1.4087   -0.8674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2669    2.2445   -1.8609 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0571    0.2808   -0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7961   -0.0975   -1.0600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6056    0.1833   -2.2767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2199    1.4588   -0.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6895    2.4627   -0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6096    1.7018    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2132   -1.6931   -0.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9775   -0.6941    0.8949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3023   -1.2977    1.0437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9338    1.2125   -1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3595   -1.1246   -2.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1320   -1.8201   -0.5432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2361   -2.6381    0.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0831   -0.8683    2.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3593    1.0737    1.2890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641    2.5499   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4426    2.1918   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  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  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
  8  6  1  0
 18 11  1  0
 19  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  8 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Epoxy-2-prenylnaphthazarin	HMDB
3,6-Dihydroxy-1a-(3-methyl-2-butenyl)naphth[2,3-b]-2,7(1ah,7ah)-dione	HMDB
2,3-Epoxy-2,3-dihydro-5,8-dihydroxy-2-(3-methyl-2-butenyl)-1,4-naphthoquinone	MeSH, HMDB
2,3-Epoxysesamone	MeSH

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-1aH,2H,7H,7aH-naphtho[2,3-b]oxirene-2,7-dione

Traditional Name

3,6-dihydroxy-1a-(3-methylbut-2-en-1-yl)-7aH-naphtho[2,3-b]oxirene-2,7-dione

CAS Registry Number

111261-12-2

SMILES

CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C15H14O5/c1-7(2)5-6-15-13(19)11-9(17)4-3-8(16)10(11)12(18)14(15)20-15/h3-5,14,16-17H,6H2,1-2H3

InChI Key

TWESJUCJKWFWQV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as vitamin k compounds. These are quinone lipids containing a methylated naphthoquinone ring structure, and vary in the aliphatic side chain attached at the 3-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Vitamin K compounds

Alternative Parents

Substituents

Naphthoquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous acid
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033333)

Source

Endogenous

Endogenous (HMDB: HMDB0033333)

Animal

Animal (HMDB: HMDB0033333)

Exogenous

Food

Food (HMDB: HMDB0033333)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0033333)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033333)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033333)

Lipid metabolism pathway (HMDB: HMDB0033333)

Cellular process

Cell signaling (HMDB: HMDB0033333)

Biochemical process

Lipid transport (HMDB: HMDB0033333)

Role

Biological role

Energy source (HMDB: HMDB0033333)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	85 - 86 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	57.73 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	1.05 g/L	ALOGPS
logP	2.45	ALOGPS
logP	3.29	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.49	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	87.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	72.08 m³·mol⁻¹	ChemAxon
Polarizability	27.33 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	164.966	31661259
DarkChem	[M-H]-	160.014	31661259
DeepCCS	[M-2H]-	190.718	30932474
DeepCCS	[M+Na]+	166.283	30932474
AllCCS	[M+H]+	162.1	32859911
AllCCS	[M+H-H2O]+	158.5	32859911
AllCCS	[M+NH4]+	165.4	32859911
AllCCS	[M+Na]+	166.4	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	165.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3-Epoxysesamone	CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O	3311.4	Standard polar	33892256
2,3-Epoxysesamone	CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O	2156.6	Standard non polar	33892256
2,3-Epoxysesamone	CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O)=C1C2=O	2246.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3-Epoxysesamone,1TMS,isomer #1	CC(C)=CCC12OC1C(=O)C1=C(O[Si](C)(C)C)C=CC(O)=C1C2=O	2283.5	Semi standard non polar	33892256
2,3-Epoxysesamone,1TMS,isomer #2	CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O[Si](C)(C)C)=C1C2=O	2259.9	Semi standard non polar	33892256
2,3-Epoxysesamone,2TMS,isomer #1	CC(C)=CCC12OC1C(=O)C1=C(O[Si](C)(C)C)C=CC(O[Si](C)(C)C)=C1C2=O	2330.6	Semi standard non polar	33892256
2,3-Epoxysesamone,1TBDMS,isomer #1	CC(C)=CCC12OC1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O)=C1C2=O	2530.5	Semi standard non polar	33892256
2,3-Epoxysesamone,1TBDMS,isomer #2	CC(C)=CCC12OC1C(=O)C1=C(O)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	2509.8	Semi standard non polar	33892256
2,3-Epoxysesamone,2TBDMS,isomer #1	CC(C)=CCC12OC1C(=O)C1=C(O[Si](C)(C)C(C)(C)C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2=O	2766.8	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 - 2,3-Epoxysesamone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-9660000000-cc32369a36830feaf47e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Epoxysesamone GC-MS (2 TMS) - 70eV, Positive	splash10-0690-9735200000-14011ee3096da8f0ee02	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Epoxysesamone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3-Epoxysesamone 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 - 2,3-Epoxysesamone 10V, Positive-QTOF	splash10-004i-0090000000-cb7e1c6f1df7d049f188	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 20V, Positive-QTOF	splash10-016r-3190000000-8a2a4b4f692d23ee9e7e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 40V, Positive-QTOF	splash10-0909-7970000000-38d2113c12e3bac30619	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 10V, Negative-QTOF	splash10-00di-0090000000-e17d6e478a0a75ffb681	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 20V, Negative-QTOF	splash10-05fr-1190000000-567e77ce1e40f87655ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 40V, Negative-QTOF	splash10-08fr-4910000000-dc98bfcb80f25af0f2c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 10V, Positive-QTOF	splash10-004i-0090000000-0ff4f807d4047e6d45c3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 20V, Positive-QTOF	splash10-004i-0190000000-c5ccc35be7fb86c6ca5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 40V, Positive-QTOF	splash10-016u-4690000000-0a397f113b10452fe25e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 10V, Negative-QTOF	splash10-00di-0090000000-cdeef1cb9497dc9eee76	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 20V, Negative-QTOF	splash10-00di-0890000000-dd7868e3c07581671081	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3-Epoxysesamone 40V, Negative-QTOF	splash10-05fv-5390000000-3c419a891c42c4712eb7	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB011360

KNApSAcK ID

C00056462

Chemspider ID

320321

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

360837

PDB ID

Not Available

ChEBI ID

174606

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1834891

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 2,3-Epoxysesamone (HMDB0033333)

MOL for HMDB0033333 (2,3-Epoxysesamone)

3D MOL for HMDB0033333 (2,3-Epoxysesamone)

3D SDF for HMDB0033333 (2,3-Epoxysesamone)

3D-SDF for HMDB0033333 (2,3-Epoxysesamone)

PDB for HMDB0033333 (2,3-Epoxysesamone)

3D PDB for HMDB0033333 (2,3-Epoxysesamone)

SMILES for HMDB0033333 (2,3-Epoxysesamone)

INCHI for HMDB0033333 (2,3-Epoxysesamone)

Structure for HMDB0033333 (2,3-Epoxysesamone)

3D Structure for HMDB0033333 (2,3-Epoxysesamone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra