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Showing metabocard for Isobergapten (HMDB0302838)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 21:03:48 UTC
Update Date2021-09-23 21:03:48 UTC
HMDB IDHMDB0302838
Secondary Accession NumbersNone
Metabolite Identification
Common NameIsobergapten
DescriptionIsobergapten is a member of the class of compounds known as angular furanocoumarins. Angular furanocoumarins are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin. Isobergapten is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Isobergapten can be found in parsnip, which makes isobergapten a potential biomarker for the consumption of this food product. Isobergapten is a non-carcinogenic (not listed by IARC) potentially toxic compound. Furocoumarin toxins can cause stomach ache and may also cause a painful skin reaction when contact with the parsnip plant is combined with UV rays from sunlight (L579) (T3DB).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302838 (Isobergapten)

Isobergapten
  Mrv1572001071617272D          

 16 18  0  0  0  0            999 V2000
    1.6283    3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 10 16  2  0  0  0  0
M  END
Download

3D MOL for HMDB0302838 (Isobergapten)

HMDB0302838
     RDKit          3D
Isobergapten
 24 26  0  0  0  0  0  0  0  0999 V2000
   -3.3061   -1.2976    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -0.1342    0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431   -0.2670    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.5223    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8415   -1.6505    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255   -2.7131    0.1661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.3667    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -0.9759   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6118   -0.5204   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    0.7196   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424    1.7776   -0.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288    2.9748   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.0107   -0.5948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    3.1837   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571    2.0859   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3773    0.8596   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3429   -1.0365    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -1.8564    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -1.9162   -0.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -2.4193    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538   -3.0112    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -0.3373   -0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721    4.1886   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345    2.2241   -0.0902 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  2  0
  8  9  1  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
  9  5  2  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
 14 23  1  0
 15 24  1  0
M  END
Download

3D SDF for HMDB0302838 (Isobergapten)

Isobergapten
  Mrv1572001071617272D          

 16 18  0  0  0  0            999 V2000
    1.6283    3.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1937    2.5420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1547   -0.9900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  5  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 10 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302838

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2

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

> <INCHI_KEY>
AJSPSRWWZBBIOR-UHFFFAOYSA-N

> <FORMULA>
C12H8O4

> <MOLECULAR_WEIGHT>
216.192

> <EXACT_MASS>
216.042258738

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
20.90285302320591

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-2H-furo[2,3-h]chromen-2-one

> <ALOGPS_LOGP>
2.06

> <JCHEM_LOGP>
1.7848117503333332

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8270283772676734

> <JCHEM_POLAR_SURFACE_AREA>
48.67

> <JCHEM_REFRACTIVITY>
56.85290000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxyfuro[2,3-h]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0302838 (Isobergapten)

HMDB0302838
     RDKit          3D
Isobergapten
 24 26  0  0  0  0  0  0  0  0999 V2000
   -3.3061   -1.2976    0.3940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5220   -0.1342    0.2058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1431   -0.2670    0.1133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5303   -1.5223    0.2031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8415   -1.6505    0.1107 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6255   -2.7131    0.1661 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768   -2.3667    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9113   -0.9759   -0.1239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6118   -0.5204   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859    0.7196   -0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7424    1.7776   -0.3345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2288    2.9748   -0.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9471    4.0107   -0.5948 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1306    3.1837   -0.3430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9571    2.0859   -0.1587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3773    0.8596   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3429   -1.0365    0.7230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8622   -1.8564    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -1.9162   -0.5237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1202   -2.4193    0.3471 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7538   -3.0112    0.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -0.3373   -0.2594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5721    4.1886   -0.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0345    2.2241   -0.0902 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  2  0
  8  9  1  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
  9  5  2  0
 16 10  2  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
 14 23  1  0
 15 24  1  0
M  END
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PDB for HMDB0302838 (Isobergapten)

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Isobergapten                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       3.039   6.054   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.228   4.745   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.719   1.616   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.832   0.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.062  -0.587   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.289  -1.848   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   16                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    3   10                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END
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3D PDB for HMDB0302838 (Isobergapten)

COMPND    HMDB0302838
HETATM    1  C1  UNL     1      -3.306  -1.298   0.394  1.00  0.00           C  
HETATM    2  O1  UNL     1      -2.522  -0.134   0.206  1.00  0.00           O  
HETATM    3  C2  UNL     1      -1.143  -0.267   0.113  1.00  0.00           C  
HETATM    4  C3  UNL     1      -0.530  -1.522   0.203  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.841  -1.651   0.111  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.625  -2.713   0.166  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.877  -2.367   0.031  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.911  -0.976  -0.124  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.612  -0.520  -0.073  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.986   0.720  -0.160  1.00  0.00           C  
HETATM   11  O3  UNL     1       1.742   1.778  -0.335  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.229   2.975  -0.426  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.947   4.011  -0.595  1.00  0.00           O  
HETATM   14  C10 UNL     1      -0.131   3.184  -0.343  1.00  0.00           C  
HETATM   15  C11 UNL     1      -0.957   2.086  -0.159  1.00  0.00           C  
HETATM   16  C12 UNL     1      -0.377   0.860  -0.069  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.343  -1.036   0.723  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.862  -1.856   1.247  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.383  -1.916  -0.524  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.120  -2.419   0.347  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.754  -3.011   0.034  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.757  -0.337  -0.259  1.00  0.00           H  
HETATM   23  H7  UNL     1      -0.572   4.189  -0.419  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.035   2.224  -0.090  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   16
CONECT    4    5   20
CONECT    5    6    9    9
CONECT    6    7
CONECT    7    8    8   21
CONECT    8    9   22
CONECT    9   10
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 HMDB0302838 (Isobergapten)

COC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2
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INCHI for HMDB0302838 (Isobergapten)

InChI=1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC12H8O4
Average Molecular Weight216.192
Monoisotopic Molecular Weight216.042258738
IUPAC Name5-methoxy-2H-furo[2,3-h]chromen-2-one
Traditional Name5-methoxyfuro[2,3-h]chromen-2-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C=CO2)C2=C1C=CC(=O)O2
InChI Identifier
InChI=1S/C12H8O4/c1-14-9-6-10-8(4-5-15-10)12-7(9)2-3-11(13)16-12/h2-6H,1H3
InChI KeyAJSPSRWWZBBIOR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as angular furanocoumarins. These are furanocoumarins, with a structure characterized by a furan ring angularly fused to a coumarin.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentAngular furanocoumarins
Alternative Parents
Substituents
  • Angular furanocoumarin
  • 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 locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB006431
KNApSAcK IDC00037321
Chemspider ID61394
KEGG Compound IDC18082
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound68082
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1637351
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available