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Showing metabocard for Bergapten (HMDB0030637)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:38:06 UTC
Update Date2022-09-22 18:34:57 UTC
HMDB IDHMDB0030637
Secondary Accession Numbers
  • HMDB30637
Metabolite Identification
Common NameBergapten
DescriptionBergapten, also known as O-methylbergaptol or heraclin, belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group. Bergapten is found, on average, in the highest concentration within a few different foods, such as anises, figs, and parsnips and in a lower concentration in carrots, fennels, and celery stalks. Bergapten has also been detected, but not quantified, in several different foods, such as coconuts, pepper (c. frutescens), corianders, sesbania flowers, and cardamoms. This could make bergapten a potential biomarker for the consumption of these foods. It is also found in rose hip, sweet marjoram, greenthread tea, and tartary buckwheat. Bergapten is a potentially toxic compound. Bergapten is a major constituent of bergamot oil (Citrus bergamia). Present in celery, especially the outer leaves, and other common grocery vegetables. Implicated in photodermatitis among grocery workers. Bergapten was under investigation in clinical trial NCT00533195 "Comparison of UVA1 Phototherapy Versus Photochemotherapy for Patients With Severe Generalized Atopic Dermatitis".
Structure
Data?1563862015
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0030637 (Bergapten)

Bergapten
  Mrv1652305201900042D          

 16 18  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
Download

3D MOL for HMDB0030637 (Bergapten)

HMDB0030637
     RDKit          3D
Bergapten
 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.9129   -2.2040   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.3555    0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642   -0.2613    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    0.9835    0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    1.4104    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.7695   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    3.1558   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151    2.1107   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    1.9965   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838    0.7650   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858    0.6400   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182   -0.5014   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843   -0.5740   -0.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -1.6485    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4239   -1.5994    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.3612    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -3.0932   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -2.4959    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -1.6796   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107    0.7508    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    3.4039   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    2.8818   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034   -2.6007    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -2.4931    0.5980 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
 14 23  1  0
 15 24  1  0
M  END
Download

3D SDF for HMDB0030637 (Bergapten)

Bergapten
  Mrv1652305201900042D          

 16 18  0  0  0  0            999 V2000
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030637

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C2C=CC(=O)OC2=CC2=C1C=CO2

> <INCHI_IDENTIFIER>
InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3

> <INCHI_KEY>
BGEBZHIAGXMEMV-UHFFFAOYSA-N

> <FORMULA>
C12H8O4

> <MOLECULAR_WEIGHT>
216.192

> <EXACT_MASS>
216.042258738

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.8726120878251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
2.12

> <JCHEM_LOGP>
1.7848117503333332

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.830371964296339

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
56.85290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.48e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bergapten

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0030637 (Bergapten)

HMDB0030637
     RDKit          3D
Bergapten
 24 26  0  0  0  0  0  0  0  0999 V2000
   -1.9129   -2.2040   -0.3534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3414   -1.3555    0.6100 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5642   -0.2613    0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1719    0.9835    0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4802    1.4104    0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586    2.7695   -0.0016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2063    3.1558   -0.1892 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4151    2.1107   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9542    1.9965   -0.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5838    0.7650   -0.0405 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8858    0.6400   -0.1437 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5182   -0.5014   -0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7843   -0.5740   -0.1145 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7997   -1.6485    0.2634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4239   -1.5994    0.3869 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8097   -0.3612    0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -3.0932   -0.5174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9262   -2.4959    0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0602   -1.6796   -1.3393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3107    0.7508    0.4321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3298    3.4039   -0.0285 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    2.8818   -0.4050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3034   -2.6007    0.3809 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483   -2.4931    0.5980 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16  3  1  0
  8  4  1  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  5 20  1  0
  6 21  1  0
  9 22  1  0
 14 23  1  0
 15 24  1  0
M  END
Download

PDB for HMDB0030637 (Bergapten)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Bergapten                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      11.592  -5.153   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       8.925  -5.153   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.554  -3.613   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.459  -4.859   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12    3   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
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3D PDB for HMDB0030637 (Bergapten)

COMPND    HMDB0030637
HETATM    1  C1  UNL     1      -1.913  -2.204  -0.353  1.00  0.00           C  
HETATM    2  O1  UNL     1      -1.341  -1.356   0.610  1.00  0.00           O  
HETATM    3  C2  UNL     1      -0.564  -0.261   0.345  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.172   0.984   0.186  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.480   1.410   0.237  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.459   2.769  -0.002  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.206   3.156  -0.189  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.415   2.111  -0.083  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.954   1.996  -0.195  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.584   0.765  -0.040  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.886   0.640  -0.144  1.00  0.00           O  
HETATM   12  C9  UNL     1       3.518  -0.501  -0.006  1.00  0.00           C  
HETATM   13  O4  UNL     1       4.784  -0.574  -0.114  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.800  -1.649   0.263  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.424  -1.599   0.387  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.810  -0.361   0.230  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.272  -3.093  -0.517  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.926  -2.496   0.049  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.060  -1.680  -1.339  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.311   0.751   0.432  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.330   3.404  -0.028  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.538   2.882  -0.405  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.303  -2.601   0.381  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.848  -2.493   0.598  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5    8
CONECT    5    6    6   20
CONECT    6    7   21
CONECT    7    8
CONECT    8    9    9
CONECT    9   10   22
CONECT   10   11   16   16
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   23
CONECT   15   16   24
END
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SMILES for HMDB0030637 (Bergapten)

COC1=C2C=CC(=O)OC2=CC2=C1C=CO2
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INCHI for HMDB0030637 (Bergapten)

InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
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Synonyms
ValueSource
4-Methoxy-7H-furo[3,2-g][1]benzopyran-7-oneChEBI
5-MethoxyfuranocoumarinChEBI
5-MethoxypsoraleneChEBI
BergapteneChEBI
HeraclinChEBI
MajudinChEBI
O-MethylbergaptolChEBI
5-MethoxypsoralenKegg
PentadermKegg
4-Methoxy-7H-furo(3,2-g)(1)benzopyran-7-oneHMDB
4-Methoxy-7H-furo[3,2-g]benzopyran-7-oneHMDB
4-Methoxy-7H-furo[3,2-g]chromen-7-oneHMDB
4-Methoxy-furo[3,2-g]chromen-7-oneHMDB
4-methoxyfuro[3,2-g]Benzopyrane-7-oneHMDB
5-Methoxy psoralenHMDB, MeSH
5-Methoxy-6,7-furanocoumarinHMDB
5-Methoxypsoralen (obsol.)HMDB
5-MOPHMDB
6-Hydroxy-4-methoxy-5-benzofuranacrylic acid, gamma-lactoneHMDB
BergaptanHMDB
PsoradermHMDB
BergaptenChEBI
5 MethoxypsoralenMeSH
5 Methoxy psoralenMeSH
Chemical FormulaC12H8O4
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
IUPAC Name4-methoxy-7H-furo[3,2-g]chromen-7-one
Traditional Namebergapten
CAS Registry Number484-20-8
SMILES
COC1=C2C=CC(=O)OC2=CC2=C1C=CO2
InChI Identifier
InChI=1S/C12H8O4/c1-14-12-7-2-3-11(13)16-10(7)6-9-8(12)4-5-15-9/h2-6H,1H3
InChI KeyBGEBZHIAGXMEMV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5-methoxypsoralens. These are psoralens containing a methoxy group attached at the C5 position of the psoralen group.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct Parent5-methoxypsoralens
Alternative Parents
Substituents
  • 5-methoxypsoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Furan
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point188 °CNot Available
Boiling Point412.00 to 413.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility810.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.035 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP2.12ALOGPS
logP1.78ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area48.67 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.85 m³·mol⁻¹ChemAxon
Polarizability20.87 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.66431661259
DarkChem[M-H]-148.08731661259
DeepCCS[M+H]+145.70730932474
DeepCCS[M-H]-143.31130932474
DeepCCS[M-2H]-177.05530932474
DeepCCS[M+Na]+151.67430932474
AllCCS[M+H]+144.732859911
AllCCS[M+H-H2O]+140.432859911
AllCCS[M+NH4]+148.832859911
AllCCS[M+Na]+150.032859911
AllCCS[M-H]-146.432859911
AllCCS[M+Na-2H]-145.932859911
AllCCS[M+HCOO]-145.432859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.5.72 minutes32390414
Predicted by Siyang on May 30, 202214.1243 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20220.94 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid30.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1860.3 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid502.1 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid187.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid295.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid210.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid464.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid554.6 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)122.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1176.6 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid395.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1305.6 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid372.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid354.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate438.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA420.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water40.2 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22929.6Standard polar33892256
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22004.0Standard non polar33892256
BergaptenCOC1=C2C=CC(=O)OC2=CC2=C1C=CO22056.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Bergapten EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten EI-B (Non-derivatized)splash10-01b9-3890000000-a8341e87fa6830843ef72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Bergapten GC-EI-TOF (Non-derivatized)splash10-00y1-3940000000-1492cacf3f4395e9f66c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergapten GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-1920000000-1f376a338d3e061368862017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Bergapten GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-01b9-7950000000-e77dc647c2fa0ccbb1772014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-qTof , Positive-QTOFsplash10-0udi-0950000000-b19407bde306a78efe772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-927b1385246a4f40d60d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0uxr-0090000000-53c9077581fc1617f7892017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0udi-0290000000-d6eb013ef1071457a5b12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0gb9-0090000000-c9f12dbc22ea5656f07c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0uxr-0190000000-7a948782b86b2057690c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-e8c8dc33e2d74b5af54a2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-ITFT , positive-QTOFsplash10-0udi-0190000000-8bc360c878c7ddfb21352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-014i-0090000000-d0dd8082e47d3cdf89c82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-0udi-0390000000-b51bcbe48eab7eb99e0f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten LC-ESI-QTOF , positive-QTOFsplash10-01b9-0900000000-187f429d7e359302ca692017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten , positive-QTOFsplash10-0udi-0950000000-b19407bde306a78efe772017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 75V, Positive-QTOFsplash10-0fk9-0940000000-ed0fbde1052e8b0f1c182021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 15V, Positive-QTOFsplash10-014i-0090000000-14415175bf4ef6e8bb112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 30V, Positive-QTOFsplash10-014i-0090000000-c2bae143550125771dd52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 15V, Positive-QTOFsplash10-0uxr-0090000000-5079706ec92060f274b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 90V, Positive-QTOFsplash10-01b9-3910000000-423ea775a61b5cb66f7c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 50V, Positive-QTOFsplash10-00dj-0900000000-54e8728fd97629535c762021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Bergapten 45V, Positive-QTOFsplash10-0uxr-0090000000-f2a40783e7a2f31ee25e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 10V, Positive-QTOFsplash10-014i-0090000000-af65171e5fbd0d0f2f8d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 20V, Positive-QTOFsplash10-014i-0190000000-f11609a8b07550b0255d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 40V, Positive-QTOFsplash10-0pic-1930000000-6fadbe89a5a3974a8f952015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 10V, Negative-QTOFsplash10-014i-0190000000-7d80d6ed97043f207cf42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 20V, Negative-QTOFsplash10-014i-0590000000-1f47d1bdb75386655f1f2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Bergapten 40V, Negative-QTOFsplash10-0a4j-0900000000-38a514b1687da9023de82015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12216
Phenol Explorer Compound ID717
FooDB IDFDB002542
KNApSAcK IDC00000575
Chemspider ID2265
KEGG Compound IDC01557
BioCyc ID5-METHOXYFURANOCOUMARIN
BiGG IDNot Available
Wikipedia LinkBergapten
METLIN IDNot Available
PubChem Compound2355
PDB IDNot Available
ChEBI ID18293
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1012251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Luszczki JJ, Andres-Mach M, Glensk M, Skalicka-Wozniak K: Anticonvulsant effects of four linear furanocoumarins, bergapten, imperatorin, oxypeucedanin, and xanthotoxin, in the mouse maximal electroshock-induced seizure model: a comparative study. Pharmacol Rep. 2010 Nov-Dec;62(6):1231-6. [PubMed:21273683 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .