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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:04:32 UTC

Update Date

2022-03-07 02:54:22 UTC

HMDB ID

HMDB0035131

Secondary Accession Numbers

HMDB35131

Metabolite Identification

Common Name

Heliannuol C

Description

Heliannuol C belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom). Heliannuol C has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make heliannuol C a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Heliannuol C.

Structure

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

HMDB0035131
     RDKit          3D
Heliannuol C
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7366    3.9095   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    2.8975   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931    1.6186    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519    1.3021    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541   -0.0523    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -0.4258    2.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -1.1137   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.8212   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436   -2.4187    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328   -1.3142   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879   -0.7153   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428   -1.5312   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -1.1332   -0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0024   -2.0117   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695    0.1200   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.5208    0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.9331    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    0.5203    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    4.8278   -0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    3.8383    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    3.0065   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227    1.7508    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    2.0468    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    1.5124   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.0154    1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -0.8098    1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -0.2183   -2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9165   -0.3634   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.8018   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -2.5645    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -2.4111    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604   -3.2851    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -2.5227   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.4911   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020   -1.3977   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -2.7389   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    1.4200    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    1.9020    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
M  END


  Mrv0541 05061308152D          

 18 19  0  0  0  0            999 V2000
    4.0527    2.0232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2401   -1.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.8374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479    1.4620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -1.0941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358    0.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720    0.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315    0.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5575    0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9865   -0.6816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7938   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4358   -1.0124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8431    0.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6188   -0.2691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6315   -1.1960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  5  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 11 10  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 14  1  0  0  0  0
 16 12  1  0  0  0  0
 17 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035131

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2=C(C=C1O)C(CC(O)C(C)(C)O2)C=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-5-10-7-14(17)15(3,4)18-13-6-9(2)12(16)8-11(10)13/h5-6,8,10,14,16-17H,1,7H2,2-4H3

> <INCHI_KEY>
DYXGWEYZDXILMS-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.629296680995242

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-ethenyl-2,2,8-trimethyl-2,3,4,5-tetrahydro-1-benzoxepine-3,7-diol

> <ALOGPS_LOGP>
2.75

> <JCHEM_LOGP>
3.004304315333333

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.963072794347475

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.181447174516709

> <JCHEM_PKA_STRONGEST_BASIC>
-3.25238457260596

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
71.6671

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-ethenyl-2,2,8-trimethyl-4,5-dihydro-3H-1-benzoxepine-3,7-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035131
     RDKit          3D
Heliannuol C
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7366    3.9095   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    2.8975   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931    1.6186    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519    1.3021    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541   -0.0523    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -0.4258    2.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -1.1137   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.8212   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436   -2.4187    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328   -1.3142   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879   -0.7153   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428   -1.5312   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -1.1332   -0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0024   -2.0117   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695    0.1200   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.5208    0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.9331    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    0.5203    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    4.8278   -0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    3.8383    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    3.0065   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227    1.7508    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    2.0468    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    1.5124   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.0154    1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -0.8098    1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -0.2183   -2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9165   -0.3634   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.8018   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -2.5645    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -2.4111    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604   -3.2851    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -2.5227   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.4911   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020   -1.3977   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -2.7389   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    1.4200    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    1.9020    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  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       7.565   3.777   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.574  -2.042   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.782  -2.233   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.280  -3.430   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.436   2.729   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.241  -2.042   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.280   0.885   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.241   1.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.907  -1.272   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.779   1.228   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.575   0.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.907   0.268   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.575  -1.272   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.948  -0.502   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.280  -1.890   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.574   1.038   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.488  -0.502   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.779  -2.233   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2    9                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    1   10                                                       
CONECT    6    9   13                                                       
CONECT    7   10   14                                                       
CONECT    8   11   12                                                       
CONECT    9    2    6   12                                                  
CONECT   10    5    7   11                                                  
CONECT   11    8   10   13                                                  
CONECT   12    8    9   16                                                  
CONECT   13    6   11   18                                                  
CONECT   14    7   15   17                                                  
CONECT   15    3    4   14   18                                             
CONECT   16   12                                                            
CONECT   17   14                                                            
CONECT   18   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0035131
HETATM    1  C1  UNL     1      -0.737   3.909  -0.121  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.102   2.898  -0.048  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.193   1.619   0.619  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.652   1.302   0.496  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.054  -0.052   0.975  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.334  -0.426   2.075  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.023  -1.114  -0.095  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.961  -0.821  -1.229  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.444  -2.419   0.549  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.733  -1.314  -0.624  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.488  -0.715  -0.369  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.543  -1.531  -0.715  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.864  -1.133  -0.545  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.002  -2.012  -0.917  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.069   0.120  -0.013  1.00  0.00           C  
HETATM   16  O3  UNL     1       4.388   0.521   0.158  1.00  0.00           O  
HETATM   17  C14 UNL     1       2.011   0.933   0.331  1.00  0.00           C  
HETATM   18  C15 UNL     1       0.692   0.520   0.155  1.00  0.00           C  
HETATM   19  H1  UNL     1      -0.470   4.828  -0.623  1.00  0.00           H  
HETATM   20  H2  UNL     1      -1.715   3.838   0.324  1.00  0.00           H  
HETATM   21  H3  UNL     1       1.078   3.006  -0.507  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.023   1.751   1.707  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.188   2.047   1.157  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.044   1.512  -0.528  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.135   0.015   1.297  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.454  -0.810   1.907  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.460  -0.218  -2.039  1.00  0.00           H  
HETATM   28  H10 UNL     1      -3.917  -0.363  -0.906  1.00  0.00           H  
HETATM   29  H11 UNL     1      -3.216  -1.802  -1.710  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.538  -2.565   0.458  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.245  -2.411   1.661  1.00  0.00           H  
HETATM   32  H14 UNL     1      -1.860  -3.285   0.164  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.350  -2.523  -1.135  1.00  0.00           H  
HETATM   34  H16 UNL     1       3.713  -2.491  -1.889  1.00  0.00           H  
HETATM   35  H17 UNL     1       4.902  -1.398  -1.162  1.00  0.00           H  
HETATM   36  H18 UNL     1       4.240  -2.739  -0.141  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.655   1.420   0.540  1.00  0.00           H  
HETATM   38  H20 UNL     1       2.250   1.902   0.743  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   21
CONECT    3    4   18   22
CONECT    4    5   23   24
CONECT    5    6    7   25
CONECT    6   26
CONECT    7    8    9   10
CONECT    8   27   28   29
CONECT    9   30   31   32
CONECT   10   11
CONECT   11   12   12   18
CONECT   12   13   33
CONECT   13   14   15   15
CONECT   14   34   35   36
CONECT   15   16   17
CONECT   16   37
CONECT   17   18   18   38
END

HMDB0035131
     RDKit          3D
Heliannuol C
 38 39  0  0  0  0  0  0  0  0999 V2000
   -0.7366    3.9095   -0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    2.8975   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1931    1.6186    0.6194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6519    1.3021    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0541   -0.0523    0.9753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -0.4258    2.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0233   -1.1137   -0.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9608   -0.8212   -1.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4436   -2.4187    0.5492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7328   -1.3142   -0.6237 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4879   -0.7153   -0.3691 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5428   -1.5312   -0.7147 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8640   -1.1332   -0.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0024   -2.0117   -0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0695    0.1200   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3883    0.5208    0.1578 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    0.9331    0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6919    0.5203    0.1552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4701    4.8278   -0.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7146    3.8383    0.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0780    3.0065   -0.5073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0227    1.7508    1.7066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1876    2.0468    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0440    1.5124   -0.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350    0.0154    1.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4536   -0.8098    1.9071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4602   -0.2183   -2.0389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9165   -0.3634   -0.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2158   -1.8018   -1.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5375   -2.5645    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2449   -2.4111    1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8604   -3.2851    0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3503   -2.5227   -1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7126   -2.4911   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9020   -1.3977   -1.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2401   -2.7389   -0.1406 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6548    1.4200    0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2498    1.9020    0.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18  3  1  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
  9 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Heliannuol C	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

5-ethenyl-2,2,8-trimethyl-2,3,4,5-tetrahydro-1-benzoxepine-3,7-diol

Traditional Name

5-ethenyl-2,2,8-trimethyl-4,5-dihydro-3H-1-benzoxepine-3,7-diol

CAS Registry Number

161730-08-1

SMILES

CC1=CC2=C(C=C1O)C(CC(O)C(C)(C)O2)C=C

InChI Identifier

InChI=1S/C15H20O3/c1-5-10-7-14(17)15(3,4)18-13-6-9(2)12(16)8-11(10)13/h5-6,8,10,14,16-17H,1,7H2,2-4H3

InChI Key

DYXGWEYZDXILMS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzoxepines. These are organic compounds containing a benzene ring fused to an oxepine ring (an unsaturated seven-membered heterocycle with one oxygen atom replacing a carbon atom).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzoxepines

Sub Class

Not Available

Direct Parent

Benzoxepines

Alternative Parents

Substituents

Benzoxepine
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Secondary alcohol
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035131)

Cellular substructure

Membrane (HMDB: HMDB0035131)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035131)

Source

Exogenous

Food

Food (HMDB: HMDB0035131)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0035131)

Not Available

Nutrient (HMDB: HMDB0035131)

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	221.2 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.9 g/L	ALOGPS
logP	2.75	ALOGPS
logP	3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	10.18	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.67 m³·mol⁻¹	ChemAxon
Polarizability	27.63 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]+	157.916	31661259
DarkChem	[M-H]-	157.287	31661259
DeepCCS	[M+H]+	159.72	30932474
DeepCCS	[M-H]-	157.362	30932474
DeepCCS	[M-2H]-	190.248	30932474
DeepCCS	[M+Na]+	165.813	30932474
AllCCS	[M+H]+	156.7	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.3	32859911
AllCCS	[M+Na]+	161.4	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol C	CC1=CC2=C(C=C1O)C(CC(O)C(C)(C)O2)C=C	3052.1	Standard polar	33892256
Heliannuol C	CC1=CC2=C(C=C1O)C(CC(O)C(C)(C)O2)C=C	1957.3	Standard non polar	33892256
Heliannuol C	CC1=CC2=C(C=C1O)C(CC(O)C(C)(C)O2)C=C	2028.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol C,1TMS,isomer #1	C=CC1CC(O)C(C)(C)OC2=CC(C)=C(O[Si](C)(C)C)C=C21	2013.6	Semi standard non polar	33892256
Heliannuol C,1TMS,isomer #2	C=CC1CC(O[Si](C)(C)C)C(C)(C)OC2=CC(C)=C(O)C=C21	1974.4	Semi standard non polar	33892256
Heliannuol C,2TMS,isomer #1	C=CC1CC(O[Si](C)(C)C)C(C)(C)OC2=CC(C)=C(O[Si](C)(C)C)C=C21	2024.7	Semi standard non polar	33892256
Heliannuol C,1TBDMS,isomer #1	C=CC1CC(O)C(C)(C)OC2=CC(C)=C(O[Si](C)(C)C(C)(C)C)C=C21	2284.4	Semi standard non polar	33892256
Heliannuol C,1TBDMS,isomer #2	C=CC1CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC(C)=C(O)C=C21	2231.8	Semi standard non polar	33892256
Heliannuol C,2TBDMS,isomer #1	C=CC1CC(O[Si](C)(C)C(C)(C)C)C(C)(C)OC2=CC(C)=C(O[Si](C)(C)C(C)(C)C)C=C21	2495.5	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 - Heliannuol C GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0490000000-e25f316366181c876daa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol C GC-MS (2 TMS) - 70eV, Positive	splash10-00b9-8029000000-72f20735476450df6665	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol 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 - Heliannuol C 10V, Positive-QTOF	splash10-0002-0190000000-5eb1db9e65a8187d2fef	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 20V, Positive-QTOF	splash10-0fc4-3950000000-a6c19131f3463eaf06c7	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 40V, Positive-QTOF	splash10-0udi-6900000000-e4e30c029e51df52b759	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 10V, Negative-QTOF	splash10-0002-0090000000-6d9afc5bf89f99670029	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 20V, Negative-QTOF	splash10-0002-0190000000-33b9824494c23df3f614	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 40V, Negative-QTOF	splash10-0229-3910000000-f44359d450b880ddead1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 20V, Negative-QTOF	splash10-004j-0960000000-69e397c8cdc49e8850f9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 40V, Negative-QTOF	splash10-03di-5980000000-549929f389fea6a03631	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 10V, Positive-QTOF	splash10-0002-0090000000-3930be7de28d17281eb5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 20V, Positive-QTOF	splash10-006t-2960000000-8542751f79c9887373ae	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol C 40V, Positive-QTOF	splash10-004i-4920000000-339955f5f5c45ddc880e	2021-09-24	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

FDB013767

KNApSAcK ID

C00037240

Chemspider ID

35013850

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751670

PDB ID

Not Available

ChEBI ID

138769

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847861

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 Heliannuol C (HMDB0035131)

MOL for HMDB0035131 (Heliannuol C)

3D MOL for HMDB0035131 (Heliannuol C)

3D SDF for HMDB0035131 (Heliannuol C)

3D-SDF for HMDB0035131 (Heliannuol C)

PDB for HMDB0035131 (Heliannuol C)

3D PDB for HMDB0035131 (Heliannuol C)

SMILES for HMDB0035131 (Heliannuol C)

INCHI for HMDB0035131 (Heliannuol C)

Structure for HMDB0035131 (Heliannuol C)

3D Structure for HMDB0035131 (Heliannuol C)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra