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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:55:45 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034133

Secondary Accession Numbers

HMDB34133

Metabolite Identification

Common Name

3-(1,1-Dimethylallyl)scopoletin

Description

3-(1,1-Dimethylallyl)scopoletin 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. 3-(1,1-Dimethylallyl)scopoletin has been detected, but not quantified in, herbs and spices. This could make 3-(1,1-dimethylallyl)scopoletin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-(1,1-Dimethylallyl)scopoletin.

Structure

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

HMDB0034133
     RDKit          3D
3-(1,1-Dimethylallyl)scopoletin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.6909    0.3333    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152    0.6076    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -0.3135    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.7006   -1.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -1.5774    0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612    0.2921   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798   -0.3099    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.2504   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172   -0.3517    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.1947   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -0.3930    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -1.6051    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.3735   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.9301   -1.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961    1.9787   -1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    1.4256   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0331    1.9911   -1.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    1.4677   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.0641   -1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142   -0.5561    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    0.9742    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.5146    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -0.2153   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -1.7943   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185   -0.4216   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093   -1.2632    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -2.3072    0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -2.0342    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -1.2353    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -1.2861    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -2.4416    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -1.4390    1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7094   -1.8481    1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614    2.7949   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    2.9006   -1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18  6  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END


  Mrv0541 05061307362D          

 19 20  0  0  0  0            999 V2000
   -1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -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
    2.1434   -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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  2  0  0  0  0
  9  6  1  0  0  0  0
  9  7  1  0  0  0  0
 10  6  2  0  0  0  0
 11  8  2  0  0  0  0
 12  8  1  0  0  0  0
 12  9  2  0  0  0  0
 13  7  2  0  0  0  0
 13 11  1  0  0  0  0
 14 10  1  0  0  0  0
 15  2  1  0  0  0  0
 15  3  1  0  0  0  0
 15  5  1  0  0  0  0
 15 10  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18  4  1  0  0  0  0
 18 13  1  0  0  0  0
 19 12  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034133

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O4/c1-5-15(2,3)10-6-9-7-13(18-4)11(16)8-12(9)19-14(10)17/h5-8,16H,1H2,2-4H3

> <INCHI_KEY>
NEUWPSXOYGGGFO-UHFFFAOYSA-N

> <FORMULA>
C15H16O4

> <MOLECULAR_WEIGHT>
260.2851

> <EXACT_MASS>
260.104859

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.444388610519326

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
2.889889077333333

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.22855584593674

> <JCHEM_PKA_STRONGEST_BASIC>
-4.883138075747999

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
72.61960000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034133
     RDKit          3D
3-(1,1-Dimethylallyl)scopoletin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.6909    0.3333    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152    0.6076    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -0.3135    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.7006   -1.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -1.5774    0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612    0.2921   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798   -0.3099    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.2504   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172   -0.3517    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.1947   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -0.3930    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -1.6051    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.3735   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.9301   -1.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961    1.9787   -1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    1.4256   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0331    1.9911   -1.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    1.4677   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.0641   -1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142   -0.5561    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    0.9742    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.5146    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -0.2153   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -1.7943   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185   -0.4216   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093   -1.2632    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -2.3072    0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -2.0342    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -1.2353    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -1.2861    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -2.4416    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -1.4390    1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7094   -1.8481    1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614    2.7949   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    2.9006   -1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18  6  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 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      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   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       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   15                                                            
CONECT    3   15                                                            
CONECT    4   18                                                            
CONECT    5    1   15                                                       
CONECT    6    9   10                                                       
CONECT    7    9   13                                                       
CONECT    8   11   12                                                       
CONECT    9    6    7   12                                                  
CONECT   10    6   14   15                                                  
CONECT   11    8   13   16                                                  
CONECT   12    8    9   19                                                  
CONECT   13    7   11   18                                                  
CONECT   14   10   17   19                                                  
CONECT   15    2    3    5   10                                             
CONECT   16   11                                                            
CONECT   17   14                                                            
CONECT   18    4   13                                                       
CONECT   19   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0034133
HETATM    1  C1  UNL     1      -4.691   0.333   1.026  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.415   0.608   0.834  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.579  -0.314   0.021  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.340  -0.701  -1.228  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.346  -1.577   0.814  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.261   0.292  -0.301  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.080  -0.310   0.107  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.142   0.250  -0.190  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.317  -0.352   0.218  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.558   0.195  -0.071  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.751  -0.393   0.330  1.00  0.00           O  
HETATM   12  C11 UNL     1       4.723  -1.605   1.066  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.589   1.373  -0.787  1.00  0.00           C  
HETATM   14  O2  UNL     1       4.829   1.930  -1.082  1.00  0.00           O  
HETATM   15  C13 UNL     1       2.396   1.979  -1.198  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.167   1.426  -0.905  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.033   1.991  -1.289  1.00  0.00           O  
HETATM   18  C15 UNL     1      -1.141   1.468  -1.012  1.00  0.00           C  
HETATM   19  O4  UNL     1      -2.191   2.064  -1.413  1.00  0.00           O  
HETATM   20  H1  UNL     1      -5.114  -0.556   0.591  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.334   0.974   1.609  1.00  0.00           H  
HETATM   22  H3  UNL     1      -3.015   1.515   1.286  1.00  0.00           H  
HETATM   23  H4  UNL     1      -4.339  -0.215  -1.272  1.00  0.00           H  
HETATM   24  H5  UNL     1      -3.526  -1.794  -1.290  1.00  0.00           H  
HETATM   25  H6  UNL     1      -2.718  -0.422  -2.124  1.00  0.00           H  
HETATM   26  H7  UNL     1      -1.809  -1.263   1.747  1.00  0.00           H  
HETATM   27  H8  UNL     1      -1.776  -2.307   0.227  1.00  0.00           H  
HETATM   28  H9  UNL     1      -3.335  -2.034   1.035  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.076  -1.235   0.671  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.296  -1.286   0.786  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.286  -2.442   0.457  1.00  0.00           H  
HETATM   32  H13 UNL     1       3.998  -1.439   1.901  1.00  0.00           H  
HETATM   33  H14 UNL     1       5.709  -1.848   1.480  1.00  0.00           H  
HETATM   34  H15 UNL     1       4.861   2.795  -1.607  1.00  0.00           H  
HETATM   35  H16 UNL     1       2.431   2.901  -1.758  1.00  0.00           H  
CONECT    1    2    2   20   21
CONECT    2    3   22
CONECT    3    4    5    6
CONECT    4   23   24   25
CONECT    5   26   27   28
CONECT    6    7    7   18
CONECT    7    8   29
CONECT    8    9    9   16
CONECT    9   10   30
CONECT   10   11   13   13
CONECT   11   12
CONECT   12   31   32   33
CONECT   13   14   15
CONECT   14   34
CONECT   15   16   16   35
CONECT   16   17
CONECT   17   18
CONECT   18   19   19
END

HMDB0034133
     RDKit          3D
3-(1,1-Dimethylallyl)scopoletin
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.6909    0.3333    1.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4152    0.6076    0.8335 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5795   -0.3135    0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3400   -0.7006   -1.2276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3462   -1.5774    0.8136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2612    0.2921   -0.3011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0798   -0.3099    0.1073 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.2504   -0.1904 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3172   -0.3517    0.2179 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5585    0.1947   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7510   -0.3930    0.3295 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7234   -1.6051    1.0663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5887    1.3735   -0.7871 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8293    1.9301   -1.0818 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961    1.9787   -1.1978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    1.4256   -0.9048 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0331    1.9911   -1.2893 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411    1.4677   -1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    2.0641   -1.4128 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1142   -0.5561    0.5910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3340    0.9742    1.6087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0146    1.5146    1.2856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3394   -0.2153   -1.2716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5258   -1.7943   -1.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7185   -0.4216   -2.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8093   -1.2632    1.7468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7764   -2.3072    0.2270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3354   -2.0342    1.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0761   -1.2353    0.6708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2962   -1.2861    0.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2862   -2.4416    0.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -1.4390    1.9007 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7094   -1.8481    1.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8614    2.7949   -1.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312    2.9006   -1.7578 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18  6  1  0
 16  8  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  5 27  1  0
  5 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(1,1-Dimethyl-2-propenyl)-7-hydroxy-6-methoxy-2H-1-benzopyran-2-one	HMDB

Chemical Formula

C₁₅H₁₆O₄

Average Molecular Weight

260.2851

Monoisotopic Molecular Weight

260.104859

IUPAC Name

7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)-2H-chromen-2-one

Traditional Name

7-hydroxy-6-methoxy-3-(2-methylbut-3-en-2-yl)chromen-2-one

CAS Registry Number

19723-23-0

SMILES

COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O

InChI Identifier

InChI=1S/C15H16O4/c1-5-15(2,3)10-6-9-7-13(18-4)11(16)8-12(9)19-14(10)17/h5-8,16H,1H2,2-4H3

InChI Key

NEUWPSXOYGGGFO-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
Anisole
1-hydroxy-2-unsubstituted benzenoid
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: HMDB0034133)
Cell membrane (HMDB: HMDB0034133)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034133)

Source

Exogenous

Exogenous (HMDB: HMDB0034133)

Food

Food (HMDB: HMDB0034133)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0034133)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034133)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	132 - 135 °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	0.12 g/L	ALOGPS
logP	3.6	ALOGPS
logP	2.89	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8.23	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	72.62 m³·mol⁻¹	ChemAxon
Polarizability	27.44 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]+	161.846	31661259
DarkChem	[M-H]-	162.726	31661259
DeepCCS	[M+H]+	161.107	30932474
DeepCCS	[M-H]-	158.749	30932474
DeepCCS	[M-2H]-	191.907	30932474
DeepCCS	[M+Na]+	167.201	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	161.0	32859911
AllCCS	[M+Na]+	162.0	32859911
AllCCS	[M-H]-	162.4	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	161.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.16 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6419 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2071.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	172.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	196.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	530.7 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	701.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	75.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1115.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1383.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	339.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	332.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	362.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(1,1-Dimethylallyl)scopoletin	COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	2991.1	Standard polar	33892256
3-(1,1-Dimethylallyl)scopoletin	COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	2219.4	Standard non polar	33892256
3-(1,1-Dimethylallyl)scopoletin	COC1=CC2=C(OC(=O)C(=C2)C(C)(C)C=C)C=C1O	2259.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(1,1-Dimethylallyl)scopoletin,1TMS,isomer #1	C=CC(C)(C)C1=CC2=CC(OC)=C(O[Si](C)(C)C)C=C2OC1=O	2355.8	Semi standard non polar	33892256
3-(1,1-Dimethylallyl)scopoletin,1TBDMS,isomer #1	C=CC(C)(C)C1=CC2=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O	2600.0	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 - 3-(1,1-Dimethylallyl)scopoletin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gea-1290000000-ffcc20d45eed11624375	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-4097000000-71d3030ec77ac06d0cc3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 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 - 3-(1,1-Dimethylallyl)scopoletin 10V, Positive-QTOF	splash10-03di-0090000000-57f6133e534c1e2efefc	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Positive-QTOF	splash10-02t9-6090000000-6daadd055cecbf1f0e4a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Positive-QTOF	splash10-014i-9240000000-65dd2878539e6d9f22c0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Negative-QTOF	splash10-0a4i-0090000000-7a17be0d67edef9921db	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Negative-QTOF	splash10-0a4i-0290000000-090da48a719b8c00882f	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Negative-QTOF	splash10-014v-2940000000-4ccf496faed16016a18b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Negative-QTOF	splash10-0a4i-0090000000-07597ad49430bb51c246	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Negative-QTOF	splash10-0690-0190000000-4a73bd762df5e781c79d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Negative-QTOF	splash10-002b-0950000000-81779eb4ca958f33f60d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 10V, Positive-QTOF	splash10-03di-0190000000-e4770cf17e3d89a593ba	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 20V, Positive-QTOF	splash10-03ei-0190000000-2bff7da49954f2b027e3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(1,1-Dimethylallyl)scopoletin 40V, Positive-QTOF	splash10-014i-1490000000-ae2b3313ba2faf4d5473	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

FDB012407

KNApSAcK ID

Not Available

Chemspider ID

4526592

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5377569

PDB ID

Not Available

ChEBI ID

174419

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.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

3-(1,1-Dimethylallyl)scopoletin → 3,4,5-trihydroxy-6-{[6-methoxy-3-(2-methylbut-3-en-2-yl)-2-oxo-2H-chromen-7-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for 3-(1,1-Dimethylallyl)scopoletin (HMDB0034133)

MOL for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

3D MOL for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

3D SDF for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

3D-SDF for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

PDB for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

3D PDB for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

SMILES for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

INCHI for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

Structure for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

3D Structure for HMDB0034133 (3-(1,1-Dimethylallyl)scopoletin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions