Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:04:35 UTC

Update Date

2022-03-07 02:54:22 UTC

HMDB ID

HMDB0035132

Secondary Accession Numbers

HMDB35132

Metabolite Identification

Common Name

Heliannuol B

Description

Heliannuol B 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 B has been detected, but not quantified in, fats and oils. This could make heliannuol b a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Heliannuol B.

Structure

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

HMDB0035132
     RDKit          3D
Heliannuol B
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3249   -2.7942    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -1.5916    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -1.2871    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -0.1486    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108    0.7299   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    0.4486   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -0.7047   -0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702   -0.9468   -1.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    1.9702   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    3.1677   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0524   -1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.5135   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    0.6428    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -0.3509    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5454   -1.1896   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813   -1.1550    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.4402    0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    0.0107    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -2.5188    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944   -3.4574    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5512   -3.3878   -0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.9503    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    1.1384   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -1.7785   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    2.1693   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    4.0114   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    2.9290    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    3.3741   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785    2.6855   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.7597   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.2576    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.4912   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592   -1.8338   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.7398   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.7974    2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0071   -2.2270    1.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.0321    1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    1.0817    0.8138 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  2  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
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  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  2  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>
HMDB0035132

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C=CC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O

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

> <INCHI_KEY>
WYQLDPBFXNVPJE-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.715085839628603

> <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-2,5-dihydro-1-benzoxepin-7-ol

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
3.1022781050000003

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.245298394327136

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.176867085612479

> <JCHEM_PKA_STRONGEST_BASIC>
-3.128922732772131

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
72.58560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.17e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035132
     RDKit          3D
Heliannuol B
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3249   -2.7942    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -1.5916    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -1.2871    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -0.1486    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108    0.7299   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    0.4486   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -0.7047   -0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702   -0.9468   -1.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    1.9702   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    3.1677   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0524   -1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.5135   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    0.6428    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -0.3509    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5454   -1.1896   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813   -1.1550    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.4402    0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    0.0107    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -2.5188    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944   -3.4574    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5512   -3.3878   -0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.9503    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    1.1384   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -1.7785   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    2.1693   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    4.0114   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    2.9290    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    3.3741   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785    2.6855   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.7597   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.2576    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.4912   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592   -1.8338   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.7398   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.7974    2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0071   -2.2270    1.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.0321    1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    1.0817    0.8138 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  2  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
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 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       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    HMDB0035132
HETATM    1  C1  UNL     1      -3.325  -2.794   0.633  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.570  -1.592   0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.331  -1.287   0.767  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.657  -0.149   0.395  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.211   0.730  -0.504  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.474   0.449  -1.037  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.121  -0.705  -0.639  1.00  0.00           C  
HETATM    8  O1  UNL     1      -4.370  -0.947  -1.190  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.674   1.970  -1.022  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.098   3.168  -0.157  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.765   2.052  -1.190  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.737   1.513  -0.516  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.754   0.643   0.639  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.910  -0.351   0.435  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.545  -1.190  -0.770  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.181  -1.155   1.660  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.008   0.440   0.082  1.00  0.00           O  
HETATM   18  O3  UNL     1       0.583   0.011   0.996  1.00  0.00           O  
HETATM   19  H1  UNL     1      -4.330  -2.519   1.038  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.794  -3.457   1.314  1.00  0.00           H  
HETATM   21  H3  UNL     1      -3.551  -3.388  -0.297  1.00  0.00           H  
HETATM   22  H4  UNL     1      -0.864  -1.950   1.474  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.918   1.138  -1.748  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.884  -1.778  -0.930  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.176   2.169  -2.014  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.450   4.011  -0.475  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.794   2.929   0.896  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.174   3.374  -0.256  1.00  0.00           H  
HETATM   29  H11 UNL     1       1.078   2.686  -2.042  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.753   1.760  -0.883  1.00  0.00           H  
HETATM   31  H13 UNL     1       2.087   1.258   1.528  1.00  0.00           H  
HETATM   32  H14 UNL     1       2.271  -0.491  -1.589  1.00  0.00           H  
HETATM   33  H15 UNL     1       3.359  -1.834  -1.114  1.00  0.00           H  
HETATM   34  H16 UNL     1       1.615  -1.740  -0.513  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.624  -0.797   2.561  1.00  0.00           H  
HETATM   36  H18 UNL     1       3.007  -2.227   1.448  1.00  0.00           H  
HETATM   37  H19 UNL     1       4.268  -1.032   1.942  1.00  0.00           H  
HETATM   38  H20 UNL     1       4.221   1.082   0.814  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   12   29
CONECT   12   13   30
CONECT   13   14   18   31
CONECT   14   15   16   17
CONECT   15   32   33   34
CONECT   16   35   36   37
CONECT   17   38
END

HMDB0035132
     RDKit          3D
Heliannuol B
 38 39  0  0  0  0  0  0  0  0999 V2000
   -3.3249   -2.7942    0.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -1.5916    0.2640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3314   -1.2871    0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6575   -0.1486    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2108    0.7299   -0.5041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4743    0.4486   -1.0370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1208   -0.7047   -0.6391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3702   -0.9468   -1.1901 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6740    1.9702   -1.0217 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0980    3.1677   -0.1571 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7653    2.0524   -1.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369    1.5135   -0.5157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7537    0.6428    0.6385 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -0.3509    0.4351 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5454   -1.1896   -0.7705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1813   -1.1550    1.6602 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0085    0.4402    0.0819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5827    0.0107    0.9955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3304   -2.5188    1.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944   -3.4574    1.3143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5512   -3.3878   -0.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.9503    1.4738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9182    1.1384   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8837   -1.7785   -0.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1757    2.1693   -2.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4502    4.0114   -0.4748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7942    2.9290    0.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1735    3.3741   -0.2556 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0785    2.6855   -2.0416 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7533    1.7597   -0.8826 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0870    1.2576    1.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2710   -0.4912   -1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3592   -1.8338   -1.1140 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6149   -1.7398   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.7974    2.5610 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0071   -2.2270    1.4477 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2683   -1.0321    1.9421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2206    1.0817    0.8138 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  2  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
 12 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,5-dihydro-1-benzoxepin-7-ol

Traditional Name

2-(2-hydroxypropan-2-yl)-5,8-dimethyl-2,5-dihydro-1-benzoxepin-7-ol

CAS Registry Number

161730-07-0

SMILES

CC1C=CC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O

InChI Identifier

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

InChI Key

WYQLDPBFXNVPJE-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: HMDB0035132)
Cell membrane (HMDB: HMDB0035132)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035132)

Source

Exogenous

Exogenous (HMDB: HMDB0035132)

Food

Food (HMDB: HMDB0035132)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035132)

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	258.2 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	0.42 g/L	ALOGPS
logP	2.67	ALOGPS
logP	3.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	10.18	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	72.59 m³·mol⁻¹	ChemAxon
Polarizability	27.72 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]+	159.888	31661259
DarkChem	[M-H]-	158.502	31661259
DeepCCS	[M+H]+	162.833	30932474
DeepCCS	[M-H]-	160.475	30932474
DeepCCS	[M-2H]-	193.361	30932474
DeepCCS	[M+Na]+	168.926	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	152.8	32859911
AllCCS	[M+NH4]+	160.5	32859911
AllCCS	[M+Na]+	161.5	32859911
AllCCS	[M-H]-	163.5	32859911
AllCCS	[M+Na-2H]-	163.6	32859911
AllCCS	[M+HCOO]-	163.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.58 minutes	32390414
Predicted by Siyang on May 30, 2022	13.5095 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.98 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2073.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	320.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	167.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	180.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	118.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	704.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	592.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1113.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	455.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1330.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	438.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	374.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	312.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	292.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol B	CC1C=CC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	3035.7	Standard polar	33892256
Heliannuol B	CC1C=CC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	1938.1	Standard non polar	33892256
Heliannuol B	CC1C=CC(OC2=C1C=C(O)C(C)=C2)C(C)(C)O	2025.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol B,1TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)C=CC(C(C)(C)O)O2	2095.8	Semi standard non polar	33892256
Heliannuol B,1TMS,isomer #2	CC1=CC2=C(C=C1O)C(C)C=CC(C(C)(C)O[Si](C)(C)C)O2	2121.5	Semi standard non polar	33892256
Heliannuol B,2TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)C=CC(C(C)(C)O[Si](C)(C)C)O2	2122.0	Semi standard non polar	33892256
Heliannuol B,1TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)C=CC(C(C)(C)O)O2	2331.8	Semi standard non polar	33892256
Heliannuol B,1TBDMS,isomer #2	CC1=CC2=C(C=C1O)C(C)C=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2	2331.8	Semi standard non polar	33892256
Heliannuol B,2TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)C=CC(C(C)(C)O[Si](C)(C)C(C)(C)C)O2	2569.4	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 B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9640000000-f552430c4da5ab307490	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol B GC-MS (2 TMS) - 70eV, Positive	splash10-0059-6928000000-886c0a5e9fe9ca927793	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol B 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 B 10V, Positive-QTOF	splash10-000t-0190000000-77f2ab83123b2067d3c7	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 20V, Positive-QTOF	splash10-001j-0790000000-95ad4302ffd8b26ef70b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 40V, Positive-QTOF	splash10-0pba-4910000000-80f0e879367193aabb45	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 10V, Negative-QTOF	splash10-0002-0090000000-639eac143bdf4221bd0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 20V, Negative-QTOF	splash10-0002-0490000000-f33aa607b1184237946e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 40V, Negative-QTOF	splash10-00di-1930000000-ccefe545e906dfe91de5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 10V, Positive-QTOF	splash10-0002-0390000000-19d5344621fac74e630a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 20V, Positive-QTOF	splash10-00dj-3940000000-4258d42a66a21d62add2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 40V, Positive-QTOF	splash10-06yc-5900000000-38500f52ce0c8c32f1a6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 10V, Negative-QTOF	splash10-0002-0090000000-94497c8e617177d2b6cd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 20V, Negative-QTOF	splash10-052b-9550000000-e1ad528a3d3916d9a355	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol B 40V, Negative-QTOF	splash10-05gi-6920000000-cf79fefbe21694ce65c4	2021-09-23	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

FDB013768

KNApSAcK ID

Not Available

Chemspider ID

35013851

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74218981

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1847871

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 B (HMDB0035132)

MOL for HMDB0035132 (Heliannuol B)

3D MOL for HMDB0035132 (Heliannuol B)

3D SDF for HMDB0035132 (Heliannuol B)

3D-SDF for HMDB0035132 (Heliannuol B)

PDB for HMDB0035132 (Heliannuol B)

3D PDB for HMDB0035132 (Heliannuol B)

SMILES for HMDB0035132 (Heliannuol B)

INCHI for HMDB0035132 (Heliannuol B)

Structure for HMDB0035132 (Heliannuol B)

3D Structure for HMDB0035132 (Heliannuol B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra