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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:46:33 UTC

Update Date

2022-03-07 02:53:10 UTC

HMDB ID

HMDB0031925

Secondary Accession Numbers

HMDB31925

Metabolite Identification

Common Name

5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran

Description

5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran, also known as 1-(5-hydroxy-2-benzofuranyl)-5-methyl-4-hexen-1-one, belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Based on a literature review very few articles have been published on 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran.

Structure

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

HMDB0031925
     RDKit          3D
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6662   -0.8806    1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    0.0580    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534    1.3224    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -0.2334   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -1.5012   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -1.2407   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -0.4809   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8152   -0.1372   -2.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -0.1447   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.4713    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.0360    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2900    0.0051    0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.6028    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.5922    1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4665    1.2285   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302    1.2478   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    0.6497   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562    0.5238   -1.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.0412    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8750   -1.8682    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5786   -0.5072    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9342    1.6459   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0009    1.2844    0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    2.0954    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.4743   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.1630   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712   -2.0529    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421   -0.6636    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297   -2.1797    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724   -1.0167    1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098   -0.4764    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8069    1.3345    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3697    1.7046   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.7463   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  9  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END


  Mrv0541 05061306142D          

 18 19  0  0  0  0            999 V2000
   -1.1801    3.2704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  4  2  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 12  8  1  0  0  0  0
 13  5  1  0  0  0  0
 14  7  2  0  0  0  0
 14 11  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031925

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCCC(=O)C1=CC2=CC(O)=CC=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O3/c1-10(2)4-3-5-13(17)15-9-11-8-12(16)6-7-14(11)18-15/h4,6-9,16H,3,5H2,1-2H3

> <INCHI_KEY>
LQWRIKCEOOIFSI-UHFFFAOYSA-N

> <FORMULA>
C15H16O3

> <MOLECULAR_WEIGHT>
244.2857

> <EXACT_MASS>
244.109944378

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.45622845987784

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(5-hydroxy-1-benzofuran-2-yl)-5-methylhex-4-en-1-one

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
3.2221339943333334

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.480730967604373

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.454382305528554

> <JCHEM_PKA_STRONGEST_BASIC>
-4.420817539774102

> <JCHEM_POLAR_SURFACE_AREA>
50.44

> <JCHEM_REFRACTIVITY>
70.9888

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.00e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(5-hydroxy-1-benzofuran-2-yl)-5-methylhex-4-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031925
     RDKit          3D
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6662   -0.8806    1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    0.0580    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534    1.3224    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -0.2334   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -1.5012   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -1.2407   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -0.4809   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8152   -0.1372   -2.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -0.1447   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.4713    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.0360    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2900    0.0051    0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.6028    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.5922    1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4665    1.2285   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302    1.2478   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    0.6497   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562    0.5238   -1.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.0412    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8750   -1.8682    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5786   -0.5072    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9342    1.6459   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0009    1.2844    0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    2.0954    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.4743   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.1630   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712   -2.0529    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421   -0.6636    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297   -2.1797    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724   -1.0167    1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098   -0.4764    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8069    1.3345    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3697    1.7046   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.7463   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  9  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.203   6.105   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.107   4.771   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.433   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.203   3.437   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.107   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.433   4.771   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.877   0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.107  -0.564   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3   10                                                       
CONECT    5    3   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   14                                                       
CONECT    8   11   12                                                       
CONECT    9   11   15                                                       
CONECT   10    1    2    4                                                  
CONECT   11    8    9   14                                                  
CONECT   12    6    8   16                                                  
CONECT   13    5   15   17                                                  
CONECT   14    7   11   18                                                  
CONECT   15    9   13   18                                                  
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0031925
HETATM    1  C1  UNL     1      -4.666  -0.881   1.283  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.224   0.058   0.222  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.953   1.322   0.025  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.185  -0.233  -0.541  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.419  -1.501  -0.374  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.997  -1.241  -0.043  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.249  -0.481  -1.061  1.00  0.00           C  
HETATM    8  O1  UNL     1      -0.815  -0.137  -2.112  1.00  0.00           O  
HETATM    9  C8  UNL     1       1.158  -0.145  -0.808  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.886  -0.471   0.316  1.00  0.00           C  
HETATM   11  C10 UNL     1       3.164   0.036   0.145  1.00  0.00           C  
HETATM   12  C11 UNL     1       4.290   0.005   0.942  1.00  0.00           C  
HETATM   13  C12 UNL     1       5.457   0.603   0.519  1.00  0.00           C  
HETATM   14  O2  UNL     1       6.618   0.592   1.299  1.00  0.00           O  
HETATM   15  C13 UNL     1       5.466   1.228  -0.717  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.330   1.248  -1.498  1.00  0.00           C  
HETATM   17  C15 UNL     1       3.141   0.650  -1.088  1.00  0.00           C  
HETATM   18  O3  UNL     1       1.956   0.524  -1.613  1.00  0.00           O  
HETATM   19  H1  UNL     1      -3.911  -1.041   2.069  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.875  -1.868   0.798  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.579  -0.507   1.784  1.00  0.00           H  
HETATM   22  H4  UNL     1      -4.934   1.646  -1.037  1.00  0.00           H  
HETATM   23  H5  UNL     1      -6.001   1.284   0.338  1.00  0.00           H  
HETATM   24  H6  UNL     1      -4.426   2.095   0.658  1.00  0.00           H  
HETATM   25  H7  UNL     1      -2.885   0.474  -1.311  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.525  -2.163  -1.258  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.871  -2.053   0.473  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.942  -0.664   0.912  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.430  -2.180   0.148  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.572  -1.017   1.193  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.310  -0.476   1.910  1.00  0.00           H  
HETATM   32  H14 UNL     1       6.807   1.334   1.967  1.00  0.00           H  
HETATM   33  H15 UNL     1       6.370   1.705  -1.072  1.00  0.00           H  
HETATM   34  H16 UNL     1       4.361   1.746  -2.468  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4    4
CONECT    3   22   23   24
CONECT    4    5   25
CONECT    5    6   26   27
CONECT    6    7   28   29
CONECT    7    8    8    9
CONECT    9   10   10   18
CONECT   10   11   30
CONECT   11   12   12   17
CONECT   12   13   31
CONECT   13   14   15   15
CONECT   14   32
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   17   18
END

HMDB0031925
     RDKit          3D
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran
 34 35  0  0  0  0  0  0  0  0999 V2000
   -4.6662   -0.8806    1.2834 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2235    0.0580    0.2224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9534    1.3224    0.0254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1847   -0.2334   -0.5406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4186   -1.5012   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9971   -1.2407   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2488   -0.4809   -1.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8152   -0.1372   -2.1120 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1579   -0.1447   -0.8081 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8859   -0.4713    0.3159 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1641    0.0360    0.1446 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2900    0.0051    0.9418 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4573    0.6028    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6180    0.5922    1.2986 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4665    1.2285   -0.7169 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3302    1.2478   -1.4980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1415    0.6497   -1.0879 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9562    0.5238   -1.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113   -1.0412    2.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8750   -1.8682    0.7978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5786   -0.5072    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9342    1.6459   -1.0374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0009    1.2844    0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4259    2.0954    0.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8854    0.4743   -1.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5251   -2.1630   -1.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8712   -2.0529    0.4730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421   -0.6636    0.9118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4297   -2.1797    0.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5724   -1.0167    1.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3098   -0.4764    1.9105 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8069    1.3345    1.9665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3697    1.7046   -1.0718 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3606    1.7463   -2.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18  9  1  0
 17 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  6 28  1  0
  6 29  1  0
 10 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(5-Hydroxy-2-benzofuranyl)-5-methyl-4-hexen-1-one	HMDB

Chemical Formula

C₁₅H₁₆O₃

Average Molecular Weight

244.2857

Monoisotopic Molecular Weight

244.109944378

IUPAC Name

1-(5-hydroxy-1-benzofuran-2-yl)-5-methylhex-4-en-1-one

Traditional Name

1-(5-hydroxy-1-benzofuran-2-yl)-5-methylhex-4-en-1-one

CAS Registry Number

197971-78-1

SMILES

CC(C)=CCCC(=O)C1=CC2=CC(O)=CC=C2O1

InChI Identifier

InChI=1S/C15H16O3/c1-10(2)4-3-5-13(17)15-9-11-8-12(16)6-7-14(11)18-15/h4,6-9,16H,3,5H2,1-2H3

InChI Key

LQWRIKCEOOIFSI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Heteroaromatic compound
Furan
Ketone
Oxacycle
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031925)
Cell membrane (HMDB: HMDB0031925)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031925)

Source

Endogenous

Endogenous (HMDB: HMDB0031925)

Plant

Plant (HMDB: HMDB0031925)

Exogenous

Food

Food (HMDB: HMDB0031925)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Beverages (FooDB: FOOD00870)

Exogenous (HMDB: HMDB0031925)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	56 - 57 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.07 g/L	ALOGPS
logP	3.66	ALOGPS
logP	3.22	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	50.44 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.99 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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]+	161.701	31661259
DarkChem	[M-H]-	159.383	31661259
DeepCCS	[M+H]+	154.881	30932474
DeepCCS	[M-H]-	152.523	30932474
DeepCCS	[M-2H]-	185.769	30932474
DeepCCS	[M+Na]+	161.073	30932474
AllCCS	[M+H]+	156.5	32859911
AllCCS	[M+H-H2O]+	152.6	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.2	32859911
AllCCS	[M-H]-	159.1	32859911
AllCCS	[M+Na-2H]-	158.9	32859911
AllCCS	[M+HCOO]-	158.8	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.	7.58 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0521 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.83 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	24.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2225.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	438.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	193.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	240.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	544.0 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	583.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1285.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	501.0 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	1224.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	427.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	436.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	330.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	270.6 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	9.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran	CC(C)=CCCC(=O)C1=CC2=CC(O)=CC=C2O1	3114.1	Standard polar	33892256
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran	CC(C)=CCCC(=O)C1=CC2=CC(O)=CC=C2O1	2115.5	Standard non polar	33892256
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran	CC(C)=CCCC(=O)C1=CC2=CC(O)=CC=C2O1	2258.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran,1TMS,isomer #1	CC(C)=CCCC(=O)C1=CC2=CC(O[Si](C)(C)C)=CC=C2O1	2246.4	Semi standard non polar	33892256
5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran,1TBDMS,isomer #1	CC(C)=CCCC(=O)C1=CC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C2O1	2489.4	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 - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-5920000000-06ec994293d1b912846d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran GC-MS (1 TMS) - 70eV, Positive	splash10-001i-6291000000-210b7d4e1857b0062e78	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 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 - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 10V, Positive-QTOF	splash10-0002-0090000000-c30daf7503c4e6c59177	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 20V, Positive-QTOF	splash10-00ls-9360000000-be97a689021180b173e5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 40V, Positive-QTOF	splash10-00xu-9400000000-2338271ee3ffad166885	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 10V, Negative-QTOF	splash10-0006-0190000000-b538ad69222bf07d0085	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 20V, Negative-QTOF	splash10-0006-0690000000-034c02803c75730c8d9e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 40V, Negative-QTOF	splash10-0a5c-3910000000-70dd7f9a631b9733b916	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 10V, Negative-QTOF	splash10-001l-0950000000-240dae9ae4c465fc62d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 20V, Negative-QTOF	splash10-001l-0950000000-5adddec053d2047a9133	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 40V, Negative-QTOF	splash10-0536-6900000000-27453379b45ebf84ef2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 10V, Positive-QTOF	splash10-0002-1290000000-f070bfd7fff15a2db5f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 20V, Positive-QTOF	splash10-0006-2590000000-e4665be267cb84a98d25	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran 40V, Positive-QTOF	splash10-0aor-8900000000-288c20fc06cd39280b0a	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

FDB008613

KNApSAcK ID

Not Available

Chemspider ID

8999487

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10824187

PDB ID

Not Available

ChEBI ID

168220

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran (HMDB0031925)

MOL for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

3D MOL for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

3D SDF for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

3D-SDF for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

PDB for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

3D PDB for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

SMILES for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

INCHI for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

Structure for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

3D Structure for HMDB0031925 (5-Hydroxy-2-(5-methyl-1-oxo-4-hexenyl)benzofuran)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra