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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:10:26 UTC

Update Date

2022-03-07 02:56:17 UTC

HMDB ID

HMDB0039644

Secondary Accession Numbers

HMDB39644

Metabolite Identification

Common Name

Heliannuol A

Description

Heliannuol A belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms. Heliannuol A has been detected, but not quantified in, fats and oils and sunflowers (Helianthus annuus). This could make heliannuol a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Heliannuol A.

Structure

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

HMDB0039644
     RDKit          3D
Heliannuol A
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9039   -2.3292    0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -1.2631    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5426   -1.5862   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -0.5916   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323    0.7530    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.0977    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.0570    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    0.3938    0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997    2.0133    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0857    3.1496   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    2.0126   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2326    1.4106   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5699    0.0942   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9477   -0.0854   -0.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.0818   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -1.1415    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.3149   -0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -1.2749   -0.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.9733   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -2.5248    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -3.2619   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006   -2.6403   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    2.1082    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -0.2947    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229    2.2554    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    2.8060   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973    3.7591    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    3.8922   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.0625   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514    1.4711   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    1.3615    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    2.0961   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1602    0.1087   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520   -0.0195    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0803    1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890   -2.1589    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -0.4232    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -3.1434    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -2.1367   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908   -2.5770   -1.6556 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
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 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
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END


  Mrv0541 05061311172D          

 18 19  0  0  0  0            999 V2000
    1.9780    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8332    3.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052    3.9156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    2.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9959    1.2978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2814    1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7103    2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7021    2.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1187    3.1187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4331    1.2978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4643    2.8510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2937    3.1187    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 14  1  0  0  0  0
 18 13  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039644

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
FWVBSUZWRAYTJB-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.234761718792697

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,6,9-tetramethyl-3,4,5,6-tetrahydro-2H-1-benzoxocine-3,8-diol

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
3.3082923016666665

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.99321852918083

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.329838378054887

> <JCHEM_PKA_STRONGEST_BASIC>
-3.23920749501721

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
71.623

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.91e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,6,9-tetramethyl-3,4,5,6-tetrahydro-1-benzoxocine-3,8-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039644
     RDKit          3D
Heliannuol A
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9039   -2.3292    0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -1.2631    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5426   -1.5862   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -0.5916   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323    0.7530    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.0977    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.0570    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    0.3938    0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997    2.0133    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0857    3.1496   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    2.0126   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2326    1.4106   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5699    0.0942   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9477   -0.0854   -0.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.0818   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -1.1415    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.3149   -0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -1.2749   -0.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.9733   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -2.5248    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -3.2619   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006   -2.6403   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    2.1082    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -0.2947    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229    2.2554    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    2.8060   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973    3.7591    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    3.8922   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.0625   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514    1.4711   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    1.3615    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    2.0961   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1602    0.1087   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520   -0.0195    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0803    1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890   -2.1589    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -0.4232    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -3.1434    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -2.1367   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908   -2.5770   -1.6556 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
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 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
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 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       3.692   0.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.808   5.503   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.155   6.592   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.423   7.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.822   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.911   3.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.859   5.503   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.859   2.423   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.282   2.104   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.525   4.733   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.193   3.193   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.525   3.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.193   4.733   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.911   4.733   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.822   5.822   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.808   2.423   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.333   5.322   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.282   5.822   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   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    HMDB0039644
HETATM    1  C1  UNL     1       3.904  -2.329   0.307  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.849  -1.263   0.244  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.543  -1.586  -0.010  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.585  -0.592  -0.065  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.932   0.753   0.137  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.239   1.098   0.395  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.166   0.057   0.439  1.00  0.00           C  
HETATM    8  O1  UNL     1       4.497   0.394   0.700  1.00  0.00           O  
HETATM    9  C8  UNL     1       0.200   2.013   0.137  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.086   3.150  -0.389  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.010   2.013  -0.783  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.233   1.411  -0.138  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.570   0.094  -0.771  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.948  -0.085  -0.895  1.00  0.00           O  
HETATM   15  C13 UNL     1      -1.945  -1.082  -0.071  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.278  -1.142   1.393  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.646  -2.315  -0.683  1.00  0.00           C  
HETATM   18  O3  UNL     1      -0.589  -1.275  -0.333  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.755  -1.973  -0.319  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.247  -2.525   1.324  1.00  0.00           H  
HETATM   21  H3  UNL     1       3.545  -3.262  -0.163  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.301  -2.640  -0.164  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.595   2.108   0.571  1.00  0.00           H  
HETATM   24  H6  UNL     1       5.210  -0.295   0.746  1.00  0.00           H  
HETATM   25  H7  UNL     1      -0.123   2.255   1.163  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.823   2.806  -1.131  1.00  0.00           H  
HETATM   27  H9  UNL     1       1.497   3.759   0.438  1.00  0.00           H  
HETATM   28  H10 UNL     1       0.452   3.892  -0.971  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.204   3.063  -1.083  1.00  0.00           H  
HETATM   30  H12 UNL     1      -0.751   1.471  -1.733  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.075   1.361   0.947  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.082   2.096  -0.324  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.160   0.109  -1.803  1.00  0.00           H  
HETATM   34  H16 UNL     1      -4.352  -0.020   0.006  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.377  -1.080   1.505  1.00  0.00           H  
HETATM   36  H18 UNL     1      -1.989  -2.159   1.750  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.722  -0.423   2.008  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.437  -3.143   0.033  1.00  0.00           H  
HETATM   39  H21 UNL     1      -3.743  -2.137  -0.757  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.191  -2.577  -1.656  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   15   33
CONECT   14   34
CONECT   15   16   17   18
CONECT   16   35   36   37
CONECT   17   38   39   40
END

HMDB0039644
     RDKit          3D
Heliannuol A
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.9039   -2.3292    0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8494   -1.2631    0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5426   -1.5862   -0.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5850   -0.5916   -0.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9323    0.7530    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2387    1.0977    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1660    0.0570    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4972    0.3938    0.7000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1997    2.0133    0.1368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0857    3.1496   -0.3890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0098    2.0126   -0.7832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2326    1.4106   -0.1379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5699    0.0942   -0.7710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9477   -0.0854   -0.8955 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9454   -1.0818   -0.0714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2781   -1.1415    1.3929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461   -2.3149   -0.6827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5890   -1.2749   -0.3334 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7553   -1.9733   -0.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2472   -2.5248    1.3236 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5449   -3.2619   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3006   -2.6403   -0.1643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5947    2.1082    0.5711 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2099   -0.2947    0.7463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1229    2.2554    1.1635 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8228    2.8060   -1.1309 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4973    3.7591    0.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4519    3.8922   -0.9711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2036    3.0625   -1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7514    1.4711   -1.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0753    1.3615    0.9474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0821    2.0961   -0.3237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1602    0.1087   -1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3520   -0.0195    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3772   -1.0803    1.5049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9890   -2.1589    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7216   -0.4232    2.0083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4375   -3.1434    0.0329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7428   -2.1367   -0.7570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908   -2.5770   -1.6556 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
 13 15  1  0
 15 16  1  0
 15 17  1  0
 15 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
 14 34  1  0
 16 35  1  0
 16 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Heliannuol a	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

2,2,6,9-tetramethyl-3,4,5,6-tetrahydro-2H-1-benzoxocine-3,8-diol

Traditional Name

2,2,6,9-tetramethyl-3,4,5,6-tetrahydro-1-benzoxocine-3,8-diol

CAS Registry Number

148054-17-5

SMILES

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

InChI Identifier

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

InChI Key

FWVBSUZWRAYTJB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxocins. Oxocins are compounds containing an oxocin ring, which is a eight-member unsaturated aromatic ring containing one oxygen atom and seven carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxocins

Sub Class

Not Available

Direct Parent

Oxocins

Alternative Parents

Substituents

Oxocin
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

Cellular substructure

Membrane (HMDB: HMDB0039644)
Cell membrane (HMDB: HMDB0039644)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039644)

Source

Exogenous

Exogenous (HMDB: HMDB0039644)

Food

Food (HMDB: HMDB0039644)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0039644)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039644)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	80 - 81 °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	0.59 g/L	ALOGPS
logP	3.33	ALOGPS
logP	3.31	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.33	ChemAxon
pKa (Strongest Basic)	-3.2	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	0	ChemAxon
Refractivity	71.62 m³·mol⁻¹	ChemAxon
Polarizability	28.23 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]+	161.566	31661259
DarkChem	[M-H]-	158.135	31661259
DeepCCS	[M+H]+	165.407	30932474
DeepCCS	[M-H]-	163.049	30932474
DeepCCS	[M-2H]-	195.935	30932474
DeepCCS	[M+Na]+	171.5	30932474
AllCCS	[M+H]+	158.1	32859911
AllCCS	[M+H-H2O]+	154.2	32859911
AllCCS	[M+NH4]+	161.8	32859911
AllCCS	[M+Na]+	162.8	32859911
AllCCS	[M-H]-	165.9	32859911
AllCCS	[M+Na-2H]-	166.2	32859911
AllCCS	[M+HCOO]-	166.6	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.	5.42 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3032 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.42 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2068.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	354.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	181.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	189.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	177.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	757.0 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	685.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	72.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1200.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	477.9 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	1462.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	316.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	307.2 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	9.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol A	CC1CCC(O)C(C)(C)OC2=C1C=C(O)C(C)=C2	2970.3	Standard polar	33892256
Heliannuol A	CC1CCC(O)C(C)(C)OC2=C1C=C(O)C(C)=C2	1974.7	Standard non polar	33892256
Heliannuol A	CC1CCC(O)C(C)(C)OC2=C1C=C(O)C(C)=C2	2062.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliannuol A,1TMS,isomer #1	CC1=CC2=C(C=C1O)C(C)CCC(O[Si](C)(C)C)C(C)(C)O2	2049.7	Semi standard non polar	33892256
Heliannuol A,1TMS,isomer #2	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(O)C(C)(C)O2	2123.0	Semi standard non polar	33892256
Heliannuol A,2TMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)CCC(O[Si](C)(C)C)C(C)(C)O2	2095.5	Semi standard non polar	33892256
Heliannuol A,1TBDMS,isomer #1	CC1=CC2=C(C=C1O)C(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2	2282.3	Semi standard non polar	33892256
Heliannuol A,1TBDMS,isomer #2	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(O)C(C)(C)O2	2360.0	Semi standard non polar	33892256
Heliannuol A,2TBDMS,isomer #1	CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)CCC(O[Si](C)(C)C(C)(C)C)C(C)(C)O2	2557.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol A GC-MS (Non-derivatized) - 70eV, Positive	splash10-01px-2690000000-38ab2b0226ac26e1a340	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol A GC-MS (2 TMS) - 70eV, Positive	splash10-004i-2119000000-23cfc70113196de060c8	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliannuol A 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 A 10V, Positive-QTOF	splash10-0udi-0190000000-b3398eecf091f2eb71f9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 20V, Positive-QTOF	splash10-0ue9-2890000000-98d8120141791d37f4bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 40V, Positive-QTOF	splash10-000b-5900000000-7c62c73ba8d0f290ca45	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 10V, Negative-QTOF	splash10-0002-0090000000-9b4bf43586f6e1345ce9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 20V, Negative-QTOF	splash10-0002-1190000000-abc6fa166742ba9cd5c2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 40V, Negative-QTOF	splash10-022a-1900000000-f3d679830a09b706870d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 10V, Positive-QTOF	splash10-0ue9-0190000000-53088195ca389582547d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 20V, Positive-QTOF	splash10-00di-1930000000-6150ee0931b0c5ec26fd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 40V, Positive-QTOF	splash10-00di-2910000000-01c7f19238ff84f3a7c9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 20V, Negative-QTOF	splash10-000t-1490000000-066e1cd915f8258ac34a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliannuol A 40V, Negative-QTOF	splash10-0159-2690000000-bbf1b8a3e45c9d1fc193	2021-09-25	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

FDB019272

KNApSAcK ID

C00037239

Chemspider ID

35014845

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15241136

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1879051

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 A (HMDB0039644)

MOL for HMDB0039644 (Heliannuol A)

3D MOL for HMDB0039644 (Heliannuol A)

3D SDF for HMDB0039644 (Heliannuol A)

3D-SDF for HMDB0039644 (Heliannuol A)

PDB for HMDB0039644 (Heliannuol A)

3D PDB for HMDB0039644 (Heliannuol A)

SMILES for HMDB0039644 (Heliannuol A)

INCHI for HMDB0039644 (Heliannuol A)

Structure for HMDB0039644 (Heliannuol A)

3D Structure for HMDB0039644 (Heliannuol A)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra