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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:04:51 UTC

Update Date

2022-03-07 02:54:22 UTC

HMDB ID

HMDB0035137

Secondary Accession Numbers

HMDB35137

Metabolite Identification

Common Name

Heliannuol D

Description

Heliannuol D 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 D has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make heliannuol D a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heliannuol D.

Structure

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

HMDB0035137
     RDKit          3D
Heliannuol D
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.4536   -2.9613   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353   -1.6435   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.6227   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4360    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3057    0.7683    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    0.7486   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -0.4432   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831   -0.4165   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396    2.1162    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.1747    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407    2.1157    1.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6714    1.5787    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    0.1038    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615   -0.5041    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -1.9116    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -0.5691   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158    0.2209    0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.6368    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7746   -3.7401    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467   -2.9574    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -3.2160   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -2.5622   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.6998   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3077   -1.2688   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.3725   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    2.8830    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388    3.5222   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    4.0820    0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    3.1952    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118    1.5671    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    1.8429   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5448    2.0503    0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.0265    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -2.5680    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205   -1.9438    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382   -2.4088    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    0.1688   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3882   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.5683   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8579   -0.4178    0.9362 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  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 13 18  1  0
  7  2  1  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
M  END

  Mrv0541 05061308152D          

 18 19  0  0  0  0            999 V2000
    2.3821    0.2130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3987    3.9775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2393    3.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    1.2008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7279    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    2.7691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2062    1.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    1.0173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4917    1.5316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9206    2.3566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3700    2.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8843    3.3325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2228    1.1191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5293    2.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5656    2.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  5  1  0  0  0  0
 10  2  1  0  0  0  0
 10  7  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  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 15  1  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035137

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3

> <INCHI_KEY>
BIIJJHXLFCDTIZ-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.345062523177376

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.3082923016666665

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.308343663872293

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.337484152401386

> <JCHEM_PKA_STRONGEST_BASIC>
-3.101350820629431

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
71.623

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035137
     RDKit          3D
Heliannuol D
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.4536   -2.9613   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353   -1.6435   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.6227   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4360    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3057    0.7683    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    0.7486   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -0.4432   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831   -0.4165   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396    2.1162    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.1747    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407    2.1157    1.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6714    1.5787    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    0.1038    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615   -0.5041    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -1.9116    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -0.5691   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158    0.2209    0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.6368    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7746   -3.7401    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467   -2.9574    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -3.2160   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -2.5622   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.6998   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3077   -1.2688   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.3725   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    2.8830    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388    3.5222   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    4.0820    0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    3.1952    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118    1.5671    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    1.8429   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5448    2.0503    0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.0265    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -2.5680    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205   -1.9438    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382   -2.4088    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    0.1688   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3882   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.5683   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8579   -0.4178    0.9362 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  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 13 18  1  0
  7  2  1  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  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       4.447   0.398   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.416   5.169   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.211   7.425   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.047   7.181   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.291   2.241   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.959   3.629   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.252   5.169   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.252   2.089   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.789   1.899   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.918   4.399   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.585   2.859   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.918   2.859   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.585   4.399   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.291   5.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.251   6.221   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.416   2.089   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.455   5.260   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.789   5.359   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6    9                                                       
CONECT    6    5   14                                                       
CONECT    7   10   13                                                       
CONECT    8   11   12                                                       
CONECT    9    1    5   11                                                  
CONECT   10    2    7   12                                                  
CONECT   11    8    9   13                                                  
CONECT   12    8   10   16                                                  
CONECT   13    7   11   18                                                  
CONECT   14    6   15   18                                                  
CONECT   15    3    4   14   17                                             
CONECT   16   12                                                            
CONECT   17   15                                                            
CONECT   18   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0035137
HETATM    1  C1  UNL     1       3.454  -2.961  -0.244  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.735  -1.643  -0.143  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.352  -1.623  -0.059  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.651  -0.436   0.034  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.306   0.768   0.048  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.694   0.749  -0.036  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.401  -0.443  -0.131  1.00  0.00           C  
HETATM    8  O1  UNL     1       4.783  -0.417  -0.212  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.740   2.116   0.141  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.722   3.175   0.507  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.441   2.116   1.109  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.671   1.579   0.403  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.753   0.104   0.667  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.062  -0.504   0.240  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.132  -1.912   0.788  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.230  -0.569  -1.246  1.00  0.00           C  
HETATM   17  O2  UNL     1      -4.116   0.221   0.788  1.00  0.00           O  
HETATM   18  O3  UNL     1      -0.711  -0.637   0.107  1.00  0.00           O  
HETATM   19  H1  UNL     1       2.775  -3.740   0.147  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.347  -2.957   0.386  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.680  -3.216  -1.293  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.821  -2.562  -0.069  1.00  0.00           H  
HETATM   23  H5  UNL     1       3.198   1.700  -0.025  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.308  -1.269  -0.281  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.334   2.372  -0.878  1.00  0.00           H  
HETATM   26  H8  UNL     1       2.308   2.883   1.393  1.00  0.00           H  
HETATM   27  H9  UNL     1       2.339   3.522  -0.345  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.127   4.082   0.821  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.641   3.195   1.341  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.212   1.567   2.035  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.590   1.843  -0.654  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.545   2.050   0.905  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.699  -0.026   1.785  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.790  -2.568   0.156  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.521  -1.944   1.829  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.138  -2.409   0.787  1.00  0.00           H  
HETATM   37  H19 UNL     1      -2.660   0.169  -1.810  1.00  0.00           H  
HETATM   38  H20 UNL     1      -4.314  -0.388  -1.503  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.991  -1.568  -1.679  1.00  0.00           H  
HETATM   40  H22 UNL     1      -4.858  -0.418   0.936  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   18
CONECT    5    6    9
CONECT    6    7    7   23
CONECT    7    8
CONECT    8   24
CONECT    9   10   11   25
CONECT   10   26   27   28
CONECT   11   12   29   30
CONECT   12   13   31   32
CONECT   13   14   18   33
CONECT   14   15   16   17
CONECT   15   34   35   36
CONECT   16   37   38   39
CONECT   17   40
END

HMDB0035137
     RDKit          3D
Heliannuol D
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.4536   -2.9613   -0.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7353   -1.6435   -0.1432 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3516   -1.6227   -0.0594 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6511   -0.4360    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3057    0.7683    0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    0.7486   -0.0360 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -0.4432   -0.1305 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7831   -0.4165   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7396    2.1162    0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7225    3.1747    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4407    2.1157    1.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6714    1.5787    0.4028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7526    0.1038    0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0615   -0.5041    0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1325   -1.9116    0.7877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2295   -0.5691   -1.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1158    0.2209    0.7880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109   -0.6368    0.1073 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7746   -3.7401    0.1474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3467   -2.9574    0.3856 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6801   -3.2160   -1.2929 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8210   -2.5622   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976    1.6998   -0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3077   -1.2688   -0.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340    2.3725   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078    2.8830    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3388    3.5222   -0.3450 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1273    4.0820    0.8207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409    3.1952    1.3408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118    1.5671    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5900    1.8429   -0.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5448    2.0503    0.9053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6994   -0.0265    1.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7902   -2.5680    0.1560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5205   -1.9438    1.8287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1382   -2.4088    0.7873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6596    0.1688   -1.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3141   -0.3882   -1.5030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9907   -1.5683   -1.6790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8579   -0.4178    0.9362 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  2  0
  7  8  1  0
  5  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14 17  1  0
 13 18  1  0
  7  2  1  0
 18  4  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  6 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Heliannuol D	HMDB
2'-Deoxytetrahydrouridine	HMDB
3,4,5,6-Tetrahydrodeoxyuridine	HMDB
5,10-Epoxy-1,3,5-bisabolatriene-2,11-diol	HMDB
tetrahydro-2'-Deoxyuridine	HMDB
THDU	HMDB
Heliannuol D	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

Traditional Name

2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,3,4,5-tetrahydro-1-benzoxepin-7-ol

CAS Registry Number

161730-09-2

SMILES

CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O

InChI Identifier

InChI=1S/C15H22O3/c1-9-5-6-14(15(3,4)17)18-13-7-10(2)12(16)8-11(9)13/h7-9,14,16-17H,5-6H2,1-4H3

InChI Key

BIIJJHXLFCDTIZ-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
Tertiary 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

Cellular substructure

Membrane (HMDB: HMDB0035137)
Cell membrane (HMDB: HMDB0035137)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035137)

Source

Exogenous

Exogenous (HMDB: HMDB0035137)

Food

Food (HMDB: HMDB0035137)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0035137)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035137)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	59 - 61 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	164.9 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	0.28 g/L	ALOGPS
logP	3.1	ALOGPS
logP	3.31	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	10.34	ChemAxon
pKa (Strongest Basic)	-3.1	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	71.62 m³·mol⁻¹	ChemAxon
Polarizability	28.35 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]+	160.593	31661259
DarkChem	[M-H]-	156.975	31661259
DeepCCS	[M+H]+	165.701	30932474
DeepCCS	[M-H]-	163.343	30932474
DeepCCS	[M-2H]-	196.228	30932474
DeepCCS	[M+Na]+	171.794	30932474
AllCCS	[M+H]+	158.3	32859911
AllCCS	[M+H-H2O]+	154.4	32859911
AllCCS	[M+NH4]+	161.8	32859911
AllCCS	[M+Na]+	162.9	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol D	CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	3011.7	Standard polar	33892256
Heliannuol D	CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	1940.5	Standard non polar	33892256
Heliannuol D	CC1CCC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	2054.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol D,1TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(C(C)(C)O)O2	2098.4	Semi standard non polar	33892256
Heliannuol D,1TMS,isomer #2	CC1=CC2=C(C=C1O)C(C)CCC(C(C)(C)O[Si](C)(C)C)O2	2103.0	Semi standard non polar	33892256
Heliannuol D,2TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(C(C)(C)O[Si](C)(C)C)O2	2123.1	Semi standard non polar	33892256
Heliannuol D,1TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(C(C)(C)O)O2	2331.0	Semi standard non polar	33892256
Heliannuol D,1TBDMS,isomer #2	CC1=CC2=C(C=C1O)C(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2	2329.0	Semi standard non polar	33892256
Heliannuol D,2TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2	2568.3	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 D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9430000000-c15af6ea487892967c42	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol D GC-MS (2 TMS) - 70eV, Positive	splash10-003r-4819000000-e0d6ff3170a90bbd55cf	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol D 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 D 10V, Positive-QTOF	splash10-0ue9-0190000000-22940b2433c959e094aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 20V, Positive-QTOF	splash10-0uyi-0890000000-a8f0be99aab549be4dc0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 40V, Positive-QTOF	splash10-05mk-4910000000-9710387b4c9a4fdd6bca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 10V, Negative-QTOF	splash10-0002-0090000000-fe01d2b814324394b9f6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 20V, Negative-QTOF	splash10-000t-0390000000-3b0ec7b6d97bb52ba913	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 40V, Negative-QTOF	splash10-00di-3910000000-35e74680c9c1b2c7d29b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 10V, Positive-QTOF	splash10-0udi-0390000000-d4861119f0d14d881e3e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 20V, Positive-QTOF	splash10-0uk9-4970000000-a22ab8d5b1feaba56823	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 40V, Positive-QTOF	splash10-0c03-5900000000-2e03514c7df437c96122	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 10V, Negative-QTOF	splash10-0002-0090000000-57a45c4032b87b6021b8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 20V, Negative-QTOF	splash10-0a4j-9170000000-6fb7db989aaf4b090c74	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol D 40V, Negative-QTOF	splash10-0596-7930000000-a109d21f0a27ee91a626	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

FDB013773

KNApSAcK ID

C00037241

Chemspider ID

9600106

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11425230

PDB ID

Not Available

ChEBI ID

174299

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847921

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 D (HMDB0035137)

MOL for HMDB0035137 (Heliannuol D)

3D MOL for HMDB0035137 (Heliannuol D)

3D SDF for HMDB0035137 (Heliannuol D)

3D-SDF for HMDB0035137 (Heliannuol D)

PDB for HMDB0035137 (Heliannuol D)

3D PDB for HMDB0035137 (Heliannuol D)

SMILES for HMDB0035137 (Heliannuol D)

INCHI for HMDB0035137 (Heliannuol D)

Structure for HMDB0035137 (Heliannuol D)

3D Structure for HMDB0035137 (Heliannuol D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra