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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:53 UTC

Update Date

2022-03-07 02:53:31 UTC

HMDB ID

HMDB0032953

Secondary Accession Numbers

HMDB32953

Metabolite Identification

Common Name

7-Methoxy-5-prenyloxycoumarin

Description

7-Methoxy-5-prenyloxycoumarin belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 7-Methoxy-5-prenyloxycoumarin has been detected, but not quantified in, citrus. This could make 7-methoxy-5-prenyloxycoumarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 7-Methoxy-5-prenyloxycoumarin.

Structure

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

HMDB0032953
     RDKit          3D
7-Methoxy-5-prenyloxycoumarin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.7920   -2.5674   -2.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -2.3313   -1.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -1.2858   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022   -1.0757   -0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -0.0106    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453    0.2348    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -0.6445    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -0.2615    1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303    0.0584    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820    0.0285   -1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228    0.4378    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    0.8484    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232    1.9215    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.7540    1.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072    2.4766    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    3.2357    1.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.4529    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    0.6441    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4315   -0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -3.3261   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861   -3.0578   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475   -1.6429   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179   -1.7408   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -0.6513   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -1.6932    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0513   -0.2511    2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3548   -1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.9845   -1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    0.7391   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    1.5185    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2293    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1884   -0.0759    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4252    2.0835    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194    3.5975    2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835   -0.5833   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 19 35  1  0
M  END

  Mrv0541 05061306492D          

 19 20  0  0  0  0            999 V2000
    2.8579   -2.4750    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
    4.2868    3.3000    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.8579    0.8250    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
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
  5  4  2  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  6  2  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  4  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 12  1  0  0  0  0
 15  5  1  0  0  0  0
 16 15  2  0  0  0  0
 17  3  1  0  0  0  0
 17 11  1  0  0  0  0
 18  7  1  0  0  0  0
 18 13  1  0  0  0  0
 19 14  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032953

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OCC=C(C)C)=C2C=CC(=O)OC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-10(2)6-7-18-13-8-11(17-3)9-14-12(13)4-5-15(16)19-14/h4-6,8-9H,7H2,1-3H3

> <INCHI_KEY>
HSJZJYCOXHKDBJ-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.75495447434324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-5-[(3-methylbut-2-en-1-yl)oxy]-2H-chromen-2-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.8292631736666665

> <ALOGPS_LOGS>
-4.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.567605664295711

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
73.59320000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-5-[(3-methylbut-2-en-1-yl)oxy]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032953
     RDKit          3D
7-Methoxy-5-prenyloxycoumarin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.7920   -2.5674   -2.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -2.3313   -1.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -1.2858   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022   -1.0757   -0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -0.0106    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453    0.2348    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -0.6445    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -0.2615    1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303    0.0584    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820    0.0285   -1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228    0.4378    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    0.8484    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232    1.9215    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.7540    1.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072    2.4766    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    3.2357    1.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.4529    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    0.6441    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4315   -0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -3.3261   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861   -3.0578   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475   -1.6429   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179   -1.7408   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -0.6513   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -1.6932    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0513   -0.2511    2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3548   -1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.9845   -1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    0.7391   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    1.5185    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2293    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1884   -0.0759    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4252    2.0835    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194    3.5975    2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835   -0.5833   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 19 35  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       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   17                                                            
CONECT    4    5   12                                                       
CONECT    5    4   15                                                       
CONECT    6    7   10                                                       
CONECT    7    6   18                                                       
CONECT    8   11   13                                                       
CONECT    9   11   14                                                       
CONECT   10    1    2    6                                                  
CONECT   11    8    9   17                                                  
CONECT   12    4   13   14                                                  
CONECT   13    8   12   18                                                  
CONECT   14    9   12   19                                                  
CONECT   15    5   16   19                                                  
CONECT   16   15                                                            
CONECT   17    3   11                                                       
CONECT   18    7   13                                                       
CONECT   19   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0032953
HETATM    1  C1  UNL     1      -3.792  -2.567  -2.340  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.505  -2.331  -1.856  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.180  -1.286  -1.000  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.902  -1.076  -0.537  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.630  -0.011   0.320  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.645   0.235   0.809  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.677  -0.645   0.403  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.982  -0.261   1.002  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.030   0.058   0.260  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.882   0.028  -1.217  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.323   0.438   0.859  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.635   0.848   0.717  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.423   1.922   1.566  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.459   2.754   1.936  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.707   2.477   1.430  1.00  0.00           C  
HETATM   16  O3  UNL     1      -4.679   3.236   1.761  1.00  0.00           O  
HETATM   17  O4  UNL     1      -3.891   1.453   0.625  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.921   0.644   0.256  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.172  -0.432  -0.604  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.703  -3.326  -3.168  1.00  0.00           H  
HETATM   21  H2  UNL     1      -4.386  -3.058  -1.553  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.248  -1.643  -2.739  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.118  -1.741  -0.843  1.00  0.00           H  
HETATM   24  H5  UNL     1       1.779  -0.651  -0.712  1.00  0.00           H  
HETATM   25  H6  UNL     1       1.425  -1.693   0.682  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.051  -0.251   2.082  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.820   0.355  -1.687  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.611  -0.985  -1.586  1.00  0.00           H  
HETATM   29  H10 UNL     1       3.065   0.739  -1.469  1.00  0.00           H  
HETATM   30  H11 UNL     1       5.479   1.519   0.694  1.00  0.00           H  
HETATM   31  H12 UNL     1       5.323   0.229   1.962  1.00  0.00           H  
HETATM   32  H13 UNL     1       6.188  -0.076   0.384  1.00  0.00           H  
HETATM   33  H14 UNL     1      -0.425   2.084   1.926  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.319   3.598   2.597  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.183  -0.583  -0.959  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5   23
CONECT    5    6   12   12
CONECT    6    7
CONECT    7    8   24   25
CONECT    8    9    9   26
CONECT    9   10   11
CONECT   10   27   28   29
CONECT   11   30   31   32
CONECT   12   13   18
CONECT   13   14   14   33
CONECT   14   15   34
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   19
CONECT   19   35
END

HMDB0032953
     RDKit          3D
7-Methoxy-5-prenyloxycoumarin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -3.7920   -2.5674   -2.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5054   -2.3313   -1.8557 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1803   -1.2858   -1.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022   -1.0757   -0.5370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6298   -0.0106    0.3203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6453    0.2348    0.8091 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6772   -0.6445    0.4033 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9816   -0.2615    1.0015 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0303    0.0584    0.2605 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8820    0.0285   -1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228    0.4378    0.8587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6352    0.8484    0.7173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4232    1.9215    1.5661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594    2.7540    1.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7072    2.4766    1.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6792    3.2357    1.7607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8912    1.4529    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9213    0.6441    0.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1723   -0.4315   -0.6036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7034   -3.3261   -3.1684 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3861   -3.0578   -1.5527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2475   -1.6429   -2.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1179   -1.7408   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792   -0.6513   -0.7116 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4252   -1.6932    0.6818 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0513   -0.2511    2.0819 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8205    0.3548   -1.6873 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6105   -0.9845   -1.5861 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0654    0.7391   -1.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4790    1.5185    0.6939 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3232    0.2293    1.9619 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1884   -0.0759    0.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4252    2.0835    1.9263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3194    3.5975    2.5968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835   -0.5833   -0.9595 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  3
  9 10  1  0
  9 11  1  0
  5 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 18 12  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 13 33  1  0
 14 34  1  0
 19 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

7-methoxy-5-[(3-methylbut-2-en-1-yl)oxy]-2H-chromen-2-one

Traditional Name

7-methoxy-5-[(3-methylbut-2-en-1-yl)oxy]chromen-2-one

CAS Registry Number

35590-41-1

SMILES

COC1=CC(OCC=C(C)C)=C2C=CC(=O)OC2=C1

InChI Identifier

InChI=1S/C15H16O4/c1-10(2)6-7-18-13-8-11(17-3)9-14-12(13)4-5-15(16)19-14/h4-6,8-9H,7H2,1-3H3

InChI Key

HSJZJYCOXHKDBJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032953)
Cell membrane (HMDB: HMDB0032953)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032953)

Source

Exogenous

Exogenous (HMDB: HMDB0032953)

Food

Food (HMDB: HMDB0032953)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Endogenous

Plant

Plant (HMDB: HMDB0032953)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0032953)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	90 - 92 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	22.1 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	0.018 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.83	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.59 m³·mol⁻¹	ChemAxon
Polarizability	27.75 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]+	161.365	31661259
DarkChem	[M-H]-	161.223	31661259
DeepCCS	[M+H]+	161.992	30932474
DeepCCS	[M-H]-	159.634	30932474
DeepCCS	[M-2H]-	192.52	30932474
DeepCCS	[M+Na]+	168.085	30932474
AllCCS	[M+H]+	157.5	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	162.9	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7-Methoxy-5-prenyloxycoumarin	COC1=CC(OCC=C(C)C)=C2C=CC(=O)OC2=C1	3161.7	Standard polar	33892256
7-Methoxy-5-prenyloxycoumarin	COC1=CC(OCC=C(C)C)=C2C=CC(=O)OC2=C1	2223.1	Standard non polar	33892256
7-Methoxy-5-prenyloxycoumarin	COC1=CC(OCC=C(C)C)=C2C=CC(=O)OC2=C1	2339.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Methoxy-5-prenyloxycoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00l6-2490000000-8ee1df0bff44f29aae16	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Methoxy-5-prenyloxycoumarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 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 - 7-Methoxy-5-prenyloxycoumarin 10V, Positive-QTOF	splash10-03di-1090000000-9b60f286421029a9b094	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 20V, Positive-QTOF	splash10-014l-9260000000-9e2f39c70b974eaefe73	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 40V, Positive-QTOF	splash10-0gbc-9710000000-fcee006d66040bc9bee7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 10V, Negative-QTOF	splash10-0a4i-0390000000-d538dd99492342eb3546	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 20V, Negative-QTOF	splash10-0006-0940000000-a15beb30ae4f362aa883	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 40V, Negative-QTOF	splash10-0002-0900000000-83735f29997d4a65ddb2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 10V, Negative-QTOF	splash10-0006-0920000000-61b137de4fbb87e9f614	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 20V, Negative-QTOF	splash10-0006-0910000000-e7137ea31c4f811400f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 40V, Negative-QTOF	splash10-03ds-1900000000-1fbd3ccd420ee284f949	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 10V, Positive-QTOF	splash10-01ox-0960000000-a510731fc159dc515990	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 20V, Positive-QTOF	splash10-0006-5910000000-47f0ad41808816206eb8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7-Methoxy-5-prenyloxycoumarin 40V, Positive-QTOF	splash10-0006-9400000000-65430fcf1c16208eb6a1	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

FDB010939

KNApSAcK ID

C00045592

Chemspider ID

23327630

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15108314

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1637271

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 7-Methoxy-5-prenyloxycoumarin (HMDB0032953)

MOL for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

3D MOL for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

3D SDF for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

3D-SDF for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

PDB for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

3D PDB for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

SMILES for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

INCHI for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

Structure for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

3D Structure for HMDB0032953 (7-Methoxy-5-prenyloxycoumarin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra