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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:55:34 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034130

Secondary Accession Numbers

HMDB34130

Metabolite Identification

Common Name

Osthenol

Description

Osthenol belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Osthenol has been detected, but not quantified in, several different foods, such as angelicas (Angelica keiskei), fennels (Foeniculum vulgare), green vegetables, and wild celeries (Apium graveolens). This could make osthenol a potential biomarker for the consumption of these foods. Osthenol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Osthenol.

Structure

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

HMDB0034130
     RDKit          3D
Osthenol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7938   -0.3976   -1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    0.1322   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6825    1.5935   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -0.7079    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -0.2443    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -0.6207    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.9203    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -2.9008    1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -2.2810    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -1.3343   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007   -0.0305   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709    0.8820   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    2.1933   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.4932   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    3.6892   -0.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712    1.5719    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3136    0.3196    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3984   -1.1592   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -0.8398   -2.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937    0.3890   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    2.1409   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    1.8446    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.9919   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.7680    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.6485    2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955    0.8615    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241   -3.8517    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -3.2890    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0369   -1.6169   -0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    0.5666   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    2.9412   -1.3465 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17  6  1  0
 17 11  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
M  END

  Mrv0541 05061307362D          

 17 18  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
  9  3  2  0  0  0  0
 10  4  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  8  1  0  0  0  0
 14 10  2  0  0  0  0
 14 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
 17 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034130

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3

> <INCHI_KEY>
RAKJVIPCCGXHHS-UHFFFAOYSA-N

> <FORMULA>
C14H14O3

> <MOLECULAR_WEIGHT>
230.2592

> <EXACT_MASS>
230.094294314

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.633239155375353

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
3.2083612930000003

> <ALOGPS_LOGS>
-3.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.642400845567916

> <JCHEM_PKA_STRONGEST_BASIC>
-6.941572258614706

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.7723

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034130
     RDKit          3D
Osthenol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7938   -0.3976   -1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    0.1322   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6825    1.5935   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -0.7079    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -0.2443    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -0.6207    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.9203    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -2.9008    1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -2.2810    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -1.3343   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007   -0.0305   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709    0.8820   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    2.1933   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.4932   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    3.6892   -0.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712    1.5719    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3136    0.3196    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3984   -1.1592   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -0.8398   -2.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937    0.3890   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    2.1409   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    1.8446    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.9919   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.7680    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.6485    2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955    0.8615    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241   -3.8517    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -3.2890    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0369   -1.6169   -0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    0.5666   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    2.9412   -1.3465 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17  6  1  0
 17 11  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  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      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3    6    9                                                       
CONECT    4    7   10                                                       
CONECT    5    8   10                                                       
CONECT    6    3   11                                                       
CONECT    7    4   12                                                       
CONECT    8    5   13                                                       
CONECT    9    1    2    3                                                  
CONECT   10    4    5   14                                                  
CONECT   11    6   12   14                                                  
CONECT   12    7   11   15                                                  
CONECT   13    8   16   17                                                  
CONECT   14   10   11   17                                                  
CONECT   15   12                                                            
CONECT   16   13                                                            
CONECT   17   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0034130
HETATM    1  C1  UNL     1      -3.794  -0.398  -1.283  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.773   0.132  -0.350  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.682   1.594  -0.088  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.947  -0.708   0.246  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.891  -0.244   1.202  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.471  -0.621   0.750  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.910  -1.920   0.879  1.00  0.00           C  
HETATM    8  O1  UNL     1       0.098  -2.901   1.428  1.00  0.00           O  
HETATM    9  C8  UNL     1       2.189  -2.281   0.458  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.030  -1.334  -0.095  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.601  -0.030  -0.229  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.471   0.882  -0.785  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.036   2.193  -0.919  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.745   2.493  -0.479  1.00  0.00           C  
HETATM   15  O2  UNL     1       1.379   3.689  -0.613  1.00  0.00           O  
HETATM   16  O3  UNL     1       0.971   1.572   0.041  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.314   0.320   0.198  1.00  0.00           C  
HETATM   18  H1  UNL     1      -4.398  -1.159  -0.774  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.273  -0.840  -2.170  1.00  0.00           H  
HETATM   20  H3  UNL     1      -4.494   0.389  -1.637  1.00  0.00           H  
HETATM   21  H4  UNL     1      -3.508   2.141  -0.620  1.00  0.00           H  
HETATM   22  H5  UNL     1      -2.753   1.845   0.987  1.00  0.00           H  
HETATM   23  H6  UNL     1      -1.696   1.992  -0.442  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.034  -1.768   0.041  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.088  -0.648   2.237  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.996   0.861   1.290  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.424  -3.852   1.522  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.533  -3.289   0.557  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.037  -1.617  -0.428  1.00  0.00           H  
HETATM   30  H13 UNL     1       4.440   0.567  -1.095  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.677   2.941  -1.346  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    3   21   22   23
CONECT    4    5   24
CONECT    5    6   25   26
CONECT    6    7    7   17
CONECT    7    8    9
CONECT    8   27
CONECT    9   10   10   28
CONECT   10   11   29
CONECT   11   12   17   17
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   15   16
CONECT   16   17
END

HMDB0034130
     RDKit          3D
Osthenol
 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.7938   -0.3976   -1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7732    0.1322   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6825    1.5935   -0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474   -0.7079    0.2463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8905   -0.2443    1.2015 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709   -0.6207    0.7497 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9101   -1.9203    0.8791 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0984   -2.9008    1.4282 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1891   -2.2810    0.4579 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0303   -1.3343   -0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007   -0.0305   -0.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4709    0.8820   -0.7855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0355    2.1933   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    2.4932   -0.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794    3.6892   -0.6131 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712    1.5719    0.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3136    0.3196    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3984   -1.1592   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2732   -0.8398   -2.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4937    0.3890   -1.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5080    2.1409   -0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7526    1.8446    0.9871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6959    1.9919   -0.4424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0342   -1.7680    0.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0877   -0.6485    2.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9955    0.8615    1.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4241   -3.8517    1.5217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5330   -3.2890    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0369   -1.6169   -0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4405    0.5666   -1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6775    2.9412   -1.3465 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17  6  1  0
 17 11  2  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-8-(3-methyl-but-2-enyl)coumarin	ChEBI
7-Hydroxy-8-prenylcoumarin	ChEBI
8-(3-Methylbut-2-en-1-yl)umbelliferone	ChEBI
8-Prenylumbelliferone	ChEBI
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one	HMDB
7-Hydroxy-8-(3-methyl-2-butenyl)-2H-1-benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₁₄H₁₄O₃

Average Molecular Weight

230.2592

Monoisotopic Molecular Weight

230.094294314

IUPAC Name

7-hydroxy-8-(3-methylbut-2-en-1-yl)-2H-chromen-2-one

Traditional Name

7-hydroxy-8-(3-methylbut-2-en-1-yl)chromen-2-one

CAS Registry Number

484-14-0

SMILES

CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C14H14O3/c1-9(2)3-6-11-12(15)7-4-10-5-8-13(16)17-14(10)11/h3-5,7-8,15H,6H2,1-2H3

InChI Key

RAKJVIPCCGXHHS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

7-hydroxycoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:81485 )
a small molecule (CPD-9838 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034130)
Cell membrane (HMDB: HMDB0034130)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034130)

Source

Exogenous

Exogenous (HMDB: HMDB0034130)

Food

Food (HMDB: HMDB0034130)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Herb

Fennel (FooDB: FOOD00082)
Angelica (FooDB: FOOD00001)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034130)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034130)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	124 - 125 °C	Not Available
Boiling Point	422.00 to 423.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	148.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.342 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.054 g/L	ALOGPS
logP	3.24	ALOGPS
logP	3.21	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.64	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	67.77 m³·mol⁻¹	ChemAxon
Polarizability	24.63 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	156.188	31661259
DarkChem	[M-H]-	150.8	31661259
DeepCCS	[M+H]+	153.351	30932474
DeepCCS	[M-H]-	150.993	30932474
DeepCCS	[M-2H]-	184.015	30932474
DeepCCS	[M+Na]+	159.444	30932474
AllCCS	[M+H]+	149.8	32859911
AllCCS	[M+H-H2O]+	145.7	32859911
AllCCS	[M+NH4]+	153.6	32859911
AllCCS	[M+Na]+	154.7	32859911
AllCCS	[M-H]-	152.8	32859911
AllCCS	[M+Na-2H]-	152.6	32859911
AllCCS	[M+HCOO]-	152.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Osthenol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2	3149.9	Standard polar	33892256
Osthenol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2	2125.1	Standard non polar	33892256
Osthenol	CC(C)=CCC1=C(O)C=CC2=C1OC(=O)C=C2	2170.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Osthenol,1TMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C=C2	2121.8	Semi standard non polar	33892256
Osthenol,1TBDMS,isomer #1	CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C=C2	2392.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Osthenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-3970000000-cbf063b17a9b1ff28fdf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Osthenol GC-MS (1 TMS) - 70eV, Positive	splash10-0abl-4090000000-75a6447476e3afd4a43f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Osthenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Osthenol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Osthenol , positive-QTOF	splash10-004i-1900000000-13a982a68db0b067c3ad	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 10V, Positive-QTOF	splash10-001i-0290000000-fe23cb680c0e7dd31c49	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 20V, Positive-QTOF	splash10-00o0-3950000000-265a49635935bcc77eb5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 40V, Positive-QTOF	splash10-01e9-5900000000-3c86d1a1a031d6b9fd55	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 10V, Negative-QTOF	splash10-004i-0290000000-0129cc47e1148c003a70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 20V, Negative-QTOF	splash10-004i-0690000000-5e2cd8fffc743828ac3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 40V, Negative-QTOF	splash10-014r-2910000000-24094198ef8b3c6f54f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 10V, Positive-QTOF	splash10-003r-0790000000-cecbb981baa3d40e1eba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 20V, Positive-QTOF	splash10-004i-0900000000-6945bc6ebaeea9278986	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 40V, Positive-QTOF	splash10-001j-0900000000-736ee822dbb9d1410fd7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 10V, Negative-QTOF	splash10-004i-0090000000-3b9ecf594e3ba8c418c2	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 20V, Negative-QTOF	splash10-004i-0290000000-6377690d47ed40e1bdf0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Osthenol 40V, Negative-QTOF	splash10-00lr-2900000000-3dda8af619d96c95b398	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5320318

PDB ID

Not Available

ChEBI ID

81485

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1050171

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 Osthenol (HMDB0034130)

MOL for HMDB0034130 (Osthenol)

3D MOL for HMDB0034130 (Osthenol)

3D SDF for HMDB0034130 (Osthenol)

3D-SDF for HMDB0034130 (Osthenol)

PDB for HMDB0034130 (Osthenol)

3D PDB for HMDB0034130 (Osthenol)

SMILES for HMDB0034130 (Osthenol)

INCHI for HMDB0034130 (Osthenol)

Structure for HMDB0034130 (Osthenol)

3D Structure for HMDB0034130 (Osthenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra