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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:12 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032689

Secondary Accession Numbers

HMDB32689

Metabolite Identification

Common Name

Annuionone C

Description

Annuionone C belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms. Annuionone C has been detected, but not quantified in, fats and oils. This could make annuionone C a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Annuionone C.

Structure

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

HMDB0032689
     RDKit          3D
Annuionone C
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.6777    1.2581    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238   -0.1014    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970   -0.5827   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179   -0.1275    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698   -0.3700    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.3675   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -1.0858   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653   -1.5845   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -2.8470    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -1.5573   -0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -0.2926   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -0.2093   -1.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    0.8792   -1.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.9018   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.0159    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    2.1415   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    1.4678    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    1.3228    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    2.0823    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476   -0.7884    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -0.2333   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.0604   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655   -0.5560    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -2.6537    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022   -3.6020   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -3.2968    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -2.3667   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.8316   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469    1.8258   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.8799   -2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    1.5307    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    0.0246    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.7123    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8463    2.9672    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    2.4077   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    1.9761    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  6  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv0541 05061306382D          

 16 17  0  0  0  0            999 V2000
    1.2856   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2856   -1.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711   -1.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -1.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558   -1.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0001   -1.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1014    0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5711    0.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0408    0.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6183    1.1198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    1.1198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808    0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5558    0.4054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1433   -0.3091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8578   -0.7216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3808    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  4 15  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 14  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032689

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)\C=C\C12OC1(C)CC(=O)CC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-9(14)5-6-13-11(2,3)7-10(15)8-12(13,4)16-13/h5-6,9,14H,7-8H2,1-4H3/b6-5+

> <INCHI_KEY>
DZVNWYFIADDOQC-AATRIKPKSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.924988221849762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-[(1E)-3-hydroxybut-1-en-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-one

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
1.5451909073333334

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.76698380645781

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.28303706718616

> <JCHEM_PKA_STRONGEST_BASIC>
-2.668409675369931

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
62.041500000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1E)-3-hydroxybut-1-en-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032689
     RDKit          3D
Annuionone C
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.6777    1.2581    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238   -0.1014    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970   -0.5827   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179   -0.1275    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698   -0.3700    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.3675   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -1.0858   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653   -1.5845   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -2.8470    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -1.5573   -0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -0.2926   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -0.2093   -1.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    0.8792   -1.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.9018   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.0159    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    2.1415   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    1.4678    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    1.3228    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    2.0823    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476   -0.7884    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -0.2333   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.0604   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655   -0.5560    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -2.6537    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022   -3.6020   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -3.2968    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -2.3667   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.8316   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469    1.8258   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.8799   -2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    1.5307    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    0.0246    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.7123    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8463    2.9672    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    2.4077   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    1.9761    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  6  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  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       2.400  -0.577   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.400  -2.117   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.066  -2.887   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.267  -2.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.037  -3.451   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.734  -2.887   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.056   1.373   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.066   0.193   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.076   1.373   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.887   2.090   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -3.347   2.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.577   0.757   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.037   0.757   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.267  -0.577   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.601  -1.347   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.577   3.424   0.000  0.00  0.00           C+0
CONECT    1    2    8                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14   15                                             
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    8                                                            
CONECT    8    1    7    9   14                                             
CONECT    9    8                                                            
CONECT   10   11                                                            
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14    4    8   13   15                                             
CONECT   15    4   14                                                       
CONECT   16   11                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0032689
HETATM    1  C1  UNL     1       3.678   1.258   1.253  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.324  -0.101   0.743  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.297  -0.583  -0.139  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.018  -0.128   0.027  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.870  -0.370   0.652  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.372  -0.367  -0.184  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.175  -1.086  -1.398  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.065  -1.584  -0.354  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.614  -2.847   0.306  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.484  -1.557  -0.808  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.856  -0.293  -1.479  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.955  -0.209  -1.999  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.957   0.879  -1.551  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.167   0.902  -0.237  1.00  0.00           C  
HETATM   15  C12 UNL     1      -2.168   1.016   0.892  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.286   2.141  -0.177  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.772   1.468   1.090  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.535   1.323   2.370  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.123   2.082   0.777  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.248  -0.788   1.633  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.072  -0.233  -1.058  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.028   0.060  -1.039  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.865  -0.556   1.711  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.144  -2.654   1.112  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.202  -3.602  -0.375  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.493  -3.297   0.811  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.595  -2.367  -1.588  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.175  -1.832  -0.002  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.547   1.826  -1.559  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.290   0.880  -2.415  1.00  0.00           H  
HETATM   31  H15 UNL     1      -3.085   1.531   0.489  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.432   0.025   1.326  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.782   1.712   1.677  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.846   2.967   0.342  1.00  0.00           H  
HETATM   35  H19 UNL     1      -0.064   2.408  -1.232  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.636   1.976   0.381  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   20
CONECT    3   21
CONECT    4    5    5   22
CONECT    5    6   23
CONECT    6    7    8   14
CONECT    7    8
CONECT    8    9   10
CONECT    9   24   25   26
CONECT   10   11   27   28
CONECT   11   12   12   13
CONECT   13   14   29   30
CONECT   14   15   16
CONECT   15   31   32   33
CONECT   16   34   35   36
END

HMDB0032689
     RDKit          3D
Annuionone C
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.6777    1.2581    1.2533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3238   -0.1014    0.7426 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2970   -0.5827   -0.1389 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0179   -0.1275    0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698   -0.3700    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3724   -0.3675   -0.1844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1746   -1.0858   -1.3984 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0653   -1.5845   -0.3541 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6136   -2.8470    0.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4841   -1.5573   -0.8075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557   -0.2926   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9551   -0.2093   -1.9989 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9568    0.8792   -1.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1671    0.9018   -0.2374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1685    1.0159    0.8921 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2861    2.1415   -0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7722    1.4678    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5349    1.3228    2.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233    2.0823    0.7768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2476   -0.7884    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0721   -0.2333   -1.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0280    0.0604   -1.0390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655   -0.5560    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1444   -2.6537    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2022   -3.6020   -0.3747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4933   -3.2968    0.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5946   -2.3667   -1.5881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1750   -1.8316   -0.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5469    1.8258   -1.5593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2904    0.8799   -2.4146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0848    1.5307    0.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4322    0.0246    1.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7820    1.7123    1.6769 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8463    2.9672    0.3424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0638    2.4077   -1.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362    1.9761    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  8  6  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 13 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,6-Epoxy-9-hydroxy-7-megastigmen-3-one	HMDB

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

6-[(1E)-3-hydroxybut-1-en-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-one

Traditional Name

6-[(1E)-3-hydroxybut-1-en-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-one

CAS Registry Number

155418-97-6

SMILES

CC(O)\C=C\C12OC1(C)CC(=O)CC2(C)C

InChI Identifier

InChI=1S/C13H20O3/c1-9(14)5-6-13-11(2,3)7-10(15)8-12(13,4)16-13/h5-6,9,14H,7-8H2,1-4H3/b6-5+

InChI Key

DZVNWYFIADDOQC-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxepanes

Sub Class

Not Available

Direct Parent

Oxepanes

Alternative Parents

Substituents

Oxepane
Cyclic ketone
Secondary alcohol
Ketone
Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032689)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032689)

Source

Endogenous

Endogenous (HMDB: HMDB0032689)

Exogenous

Food

Food (HMDB: HMDB0032689)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0032689)

Role

Biological role

Energy source (HMDB: HMDB0032689)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032689)

Emulsifier (HMDB: HMDB0032689)

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	1.61 g/L	ALOGPS
logP	1.45	ALOGPS
logP	1.55	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	15.28	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.04 m³·mol⁻¹	ChemAxon
Polarizability	24.92 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]+	153.106	31661259
DarkChem	[M-H]-	152.386	31661259
DeepCCS	[M-2H]-	187.537	30932474
DeepCCS	[M+Na]+	163.064	30932474
AllCCS	[M+H]+	152.2	32859911
AllCCS	[M+H-H2O]+	148.4	32859911
AllCCS	[M+NH4]+	155.6	32859911
AllCCS	[M+Na]+	156.6	32859911
AllCCS	[M-H]-	157.9	32859911
AllCCS	[M+Na-2H]-	158.4	32859911
AllCCS	[M+HCOO]-	159.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annuionone C	CC(O)\C=C\C12OC1(C)CC(=O)CC2(C)C	2735.7	Standard polar	33892256
Annuionone C	CC(O)\C=C\C12OC1(C)CC(=O)CC2(C)C	1673.8	Standard non polar	33892256
Annuionone C	CC(O)\C=C\C12OC1(C)CC(=O)CC2(C)C	1639.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annuionone C,1TMS,isomer #1	CC(/C=C/C12OC1(C)CC(=O)CC2(C)C)O[Si](C)(C)C	1778.0	Semi standard non polar	33892256
Annuionone C,1TMS,isomer #2	CC(O)/C=C/C12OC1(C)CC(O[Si](C)(C)C)=CC2(C)C	1756.0	Semi standard non polar	33892256
Annuionone C,1TMS,isomer #3	CC(O)/C=C/C12OC1(C)C=C(O[Si](C)(C)C)CC2(C)C	1757.6	Semi standard non polar	33892256
Annuionone C,2TMS,isomer #1	CC(/C=C/C12OC1(C)CC(O[Si](C)(C)C)=CC2(C)C)O[Si](C)(C)C	1760.1	Semi standard non polar	33892256
Annuionone C,2TMS,isomer #1	CC(/C=C/C12OC1(C)CC(O[Si](C)(C)C)=CC2(C)C)O[Si](C)(C)C	1774.3	Standard non polar	33892256
Annuionone C,2TMS,isomer #2	CC(/C=C/C12OC1(C)C=C(O[Si](C)(C)C)CC2(C)C)O[Si](C)(C)C	1770.8	Semi standard non polar	33892256
Annuionone C,2TMS,isomer #2	CC(/C=C/C12OC1(C)C=C(O[Si](C)(C)C)CC2(C)C)O[Si](C)(C)C	1769.0	Standard non polar	33892256
Annuionone C,1TBDMS,isomer #1	CC(/C=C/C12OC1(C)CC(=O)CC2(C)C)O[Si](C)(C)C(C)(C)C	2018.0	Semi standard non polar	33892256
Annuionone C,1TBDMS,isomer #2	CC(O)/C=C/C12OC1(C)CC(O[Si](C)(C)C(C)(C)C)=CC2(C)C	2013.6	Semi standard non polar	33892256
Annuionone C,1TBDMS,isomer #3	CC(O)/C=C/C12OC1(C)C=C(O[Si](C)(C)C(C)(C)C)CC2(C)C	2021.9	Semi standard non polar	33892256
Annuionone C,2TBDMS,isomer #1	CC(/C=C/C12OC1(C)CC(O[Si](C)(C)C(C)(C)C)=CC2(C)C)O[Si](C)(C)C(C)(C)C	2231.9	Semi standard non polar	33892256
Annuionone C,2TBDMS,isomer #1	CC(/C=C/C12OC1(C)CC(O[Si](C)(C)C(C)(C)C)=CC2(C)C)O[Si](C)(C)C(C)(C)C	2251.7	Standard non polar	33892256
Annuionone C,2TBDMS,isomer #2	CC(/C=C/C12OC1(C)C=C(O[Si](C)(C)C(C)(C)C)CC2(C)C)O[Si](C)(C)C(C)(C)C	2259.2	Semi standard non polar	33892256
Annuionone C,2TBDMS,isomer #2	CC(/C=C/C12OC1(C)C=C(O[Si](C)(C)C(C)(C)C)CC2(C)C)O[Si](C)(C)C(C)(C)C	2242.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone C GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9620000000-8aa20eafdd3238daa52f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone C GC-MS (1 TMS) - 70eV, Positive	splash10-001r-9140000000-443ced134b14cb34c91c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuionone C 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 - Annuionone C 10V, Positive-QTOF	splash10-0a4i-0190000000-d0608a98276df5564412	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 20V, Positive-QTOF	splash10-0a4r-5690000000-934e2bc48cf0e3ec41ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 40V, Positive-QTOF	splash10-0a4i-9300000000-4ae2742bf82afd36c2a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 10V, Negative-QTOF	splash10-00di-0190000000-bad832d3812364abe424	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 20V, Negative-QTOF	splash10-05fr-0290000000-831ef9beb410825d53db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 40V, Negative-QTOF	splash10-052r-4910000000-0af8a48171be85bd67f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 10V, Positive-QTOF	splash10-0a6r-0390000000-0d74f6da5cbe28599bba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 20V, Positive-QTOF	splash10-0550-2690000000-40eff9298f999e582669	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 40V, Positive-QTOF	splash10-0a5l-9430000000-afef114274b91e74aafc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 10V, Negative-QTOF	splash10-00fr-0790000000-2dbd91801dbfd7ec5cc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 20V, Negative-QTOF	splash10-0uk9-0950000000-438901aabc0b3295b7d5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuionone C 40V, Negative-QTOF	splash10-0h2r-1930000000-1160b15ad1e423b8ea17	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB010646

KNApSAcK ID

C00052704

Chemspider ID

8096559

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9920924

PDB ID

Not Available

ChEBI ID

168292

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 Annuionone C (HMDB0032689)

MOL for HMDB0032689 (Annuionone C)

3D MOL for HMDB0032689 (Annuionone C)

3D SDF for HMDB0032689 (Annuionone C)

3D-SDF for HMDB0032689 (Annuionone C)

PDB for HMDB0032689 (Annuionone C)

3D PDB for HMDB0032689 (Annuionone C)

SMILES for HMDB0032689 (Annuionone C)

INCHI for HMDB0032689 (Annuionone C)

Structure for HMDB0032689 (Annuionone C)

3D Structure for HMDB0032689 (Annuionone C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra