Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:17:43 UTC

Update Date

2022-03-07 02:53:46 UTC

HMDB ID

HMDB0033559

Secondary Accession Numbers

HMDB33559

Metabolite Identification

Common Name

7,7'-Dihydroxy-6,8'-bicoumarin

Description

7,7'-Dihydroxy-6,8'-bicoumarin 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. 7,7'-Dihydroxy-6,8'-bicoumarin has been detected, but not quantified in, several different foods, such as pulses, teas (Camellia sinensis), red tea, herbs and spices, and herbal tea. This could make 7,7'-dihydroxy-6,8'-bicoumarin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 7,7'-Dihydroxy-6,8'-bicoumarin.

Structure

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

HMDB0033559
     RDKit          3D
7,7'-Dihydroxy-6,8'-bicoumarin
 34 37  0  0  0  0  0  0  0  0999 V2000
    6.1868    0.8825    1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    0.8209    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5427    1.9119    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623    1.8866   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.7629    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239    0.7264   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112   -0.3871   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -0.4610   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.9707   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.4414   -2.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.0319   -2.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -0.5680   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083   -0.0602   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3210    0.4195    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    0.9143    1.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    0.9457    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564    1.4140    3.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090    0.4830    1.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.0025    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.4412    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -2.5439    0.7887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2231   -1.4157    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -0.2825    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -0.2311    1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583    2.7902    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    2.7346   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483    1.5644   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -1.4245   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7212   -1.4445   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143   -0.6093   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477    0.3889    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7354    1.2878    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -3.3694    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -2.2488    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 19  8  1  0
 19 13  2  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  1  0
M  END


  Mrv0541 05061307112D          

 24 27  0  0  0  0            999 V2000
    0.7145    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
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  2  2  0  0  0  0
  6  3  2  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 13  8  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  6  1  0  0  0  0
 16  5  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  2  0  0  0  0
 18  9  2  0  0  0  0
 18 17  1  0  0  0  0
 19 12  1  0  0  0  0
 20 13  1  0  0  0  0
 21 15  2  0  0  0  0
 22 16  2  0  0  0  0
 23 14  1  0  0  0  0
 23 15  1  0  0  0  0
 24 16  1  0  0  0  0
 24 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033559

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H10O6/c19-12-4-1-9-2-5-16(22)24-18(9)17(12)11-7-10-3-6-15(21)23-14(10)8-13(11)20/h1-8,19-20H

> <INCHI_KEY>
GGNRJMYAXINNLX-UHFFFAOYSA-N

> <FORMULA>
C18H10O6

> <MOLECULAR_WEIGHT>
322.2684

> <EXACT_MASS>
322.047738052

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.022327645739765

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6-(7-hydroxy-2-oxo-2H-chromen-8-yl)-2H-chromen-2-one

> <ALOGPS_LOGP>
2.93

> <JCHEM_LOGP>
2.6335681333333327

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.9353294557317975

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.981040326270615

> <JCHEM_PKA_STRONGEST_BASIC>
-6.640654590362546

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
86.13719999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6-(7-hydroxy-2-oxochromen-8-yl)chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033559
     RDKit          3D
7,7'-Dihydroxy-6,8'-bicoumarin
 34 37  0  0  0  0  0  0  0  0999 V2000
    6.1868    0.8825    1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    0.8209    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5427    1.9119    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623    1.8866   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.7629    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239    0.7264   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112   -0.3871   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -0.4610   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.9707   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.4414   -2.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.0319   -2.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -0.5680   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083   -0.0602   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3210    0.4195    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    0.9143    1.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    0.9457    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564    1.4140    3.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090    0.4830    1.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.0025    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.4412    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -2.5439    0.7887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2231   -1.4157    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -0.2825    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -0.2311    1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583    2.7902    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    2.7346   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483    1.5644   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -1.4245   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7212   -1.4445   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143   -0.6093   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477    0.3889    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7354    1.2878    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -3.3694    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -2.2488    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 19  8  1  0
 19 13  2  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667  15.400   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       1.334  13.090   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    4    9                                                       
CONECT    2    5    9                                                       
CONECT    3    6   10                                                       
CONECT    4    1   12                                                       
CONECT    5    2   16                                                       
CONECT    6    3   15                                                       
CONECT    7   10   11                                                       
CONECT    8   13   14                                                       
CONECT    9    1    2   18                                                  
CONECT   10    3    7   14                                                  
CONECT   11    7   13   17                                                  
CONECT   12    4   17   19                                                  
CONECT   13    8   11   20                                                  
CONECT   14    8   10   23                                                  
CONECT   15    6   21   23                                                  
CONECT   16    5   22   24                                                  
CONECT   17   11   12   18                                                  
CONECT   18    9   17   24                                                  
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   15                                                            
CONECT   22   16                                                            
CONECT   23   14   15                                                       
CONECT   24   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   54    0
END

COMPND    HMDB0033559
HETATM    1  O1  UNL     1       6.187   0.882   1.601  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.994   0.821   1.145  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.543   1.912   0.433  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.262   1.887  -0.076  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.507   0.763   0.160  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.224   0.726  -0.345  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.411  -0.387  -0.137  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.949  -0.461  -0.656  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.260  -0.971  -1.899  1.00  0.00           C  
HETATM   10  O2  UNL     1      -0.237  -1.441  -2.712  1.00  0.00           O  
HETATM   11  C9  UNL     1      -2.554  -1.032  -2.372  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.602  -0.568  -1.581  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.308  -0.060  -0.346  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.321   0.420   0.489  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.936   0.914   1.718  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.614   0.946   2.129  1.00  0.00           C  
HETATM   17  O3  UNL     1      -2.356   1.414   3.265  1.00  0.00           O  
HETATM   18  O4  UNL     1      -1.709   0.483   1.305  1.00  0.00           O  
HETATM   19  C15 UNL     1      -2.002  -0.003   0.121  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.933  -1.441   0.585  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.123  -2.544   0.789  1.00  0.00           O  
HETATM   22  C17 UNL     1       2.223  -1.416   1.098  1.00  0.00           C  
HETATM   23  C18 UNL     1       3.025  -0.283   0.877  1.00  0.00           C  
HETATM   24  O6  UNL     1       4.244  -0.231   1.348  1.00  0.00           O  
HETATM   25  H1  UNL     1       5.158   2.790   0.259  1.00  0.00           H  
HETATM   26  H2  UNL     1       2.859   2.735  -0.651  1.00  0.00           H  
HETATM   27  H3  UNL     1       0.848   1.564  -0.903  1.00  0.00           H  
HETATM   28  H4  UNL     1       0.733  -1.424  -2.424  1.00  0.00           H  
HETATM   29  H5  UNL     1      -2.721  -1.444  -3.357  1.00  0.00           H  
HETATM   30  H6  UNL     1      -4.614  -0.609  -1.936  1.00  0.00           H  
HETATM   31  H7  UNL     1      -5.348   0.389   0.155  1.00  0.00           H  
HETATM   32  H8  UNL     1      -4.735   1.288   2.365  1.00  0.00           H  
HETATM   33  H9  UNL     1       0.402  -3.369   1.302  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.589  -2.249   1.650  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   24
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   23
CONECT    6    7   27
CONECT    7    8   20   20
CONECT    8    9    9   19
CONECT    9   10   11
CONECT   10   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   19   19
CONECT   14   15   15   31
CONECT   15   16   32
CONECT   16   17   17   18
CONECT   18   19
CONECT   20   21   22
CONECT   21   33
CONECT   22   23   23   34
CONECT   23   24
END

HMDB0033559
     RDKit          3D
7,7'-Dihydroxy-6,8'-bicoumarin
 34 37  0  0  0  0  0  0  0  0999 V2000
    6.1868    0.8825    1.6009 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9938    0.8209    1.1448 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5427    1.9119    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2623    1.8866   -0.0761 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5071    0.7629    0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2239    0.7264   -0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4112   -0.3871   -0.1374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9493   -0.4610   -0.6558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2596   -0.9707   -1.8995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2366   -1.4414   -2.7115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -1.0319   -2.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6016   -0.5680   -1.5814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3083   -0.0602   -0.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3210    0.4195    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9355    0.9143    1.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6144    0.9457    2.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564    1.4140    3.2646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090    0.4830    1.3048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0021   -0.0025    0.1208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9329   -1.4412    0.5850 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1233   -2.5439    0.7887 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2231   -1.4157    1.0982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0254   -0.2825    0.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -0.2311    1.3484 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1583    2.7902    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8586    2.7346   -0.6507 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8483    1.5644   -0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -1.4245   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7212   -1.4445   -3.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143   -0.6093   -1.9358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3477    0.3889    0.1553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7354    1.2878    2.3652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4022   -3.3694    1.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -2.2488    1.6501 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
  7 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24  2  1  0
 23  5  1  0
 19  8  1  0
 19 13  2  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 21 33  1  0
 22 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7,7'-Dihydroxy[6,8'-bi-2H-1-benzopyran]-2,2'-dione	HMDB

Chemical Formula

C₁₈H₁₀O₆

Average Molecular Weight

322.2684

Monoisotopic Molecular Weight

322.047738052

IUPAC Name

7-hydroxy-6-(7-hydroxy-2-oxo-2H-chromen-8-yl)-2H-chromen-2-one

Traditional Name

7-hydroxy-6-(7-hydroxy-2-oxochromen-8-yl)chromen-2-one

CAS Registry Number

15575-52-7

SMILES

OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2

InChI Identifier

InChI=1S/C18H10O6/c19-12-4-1-9-2-5-16(22)24-18(9)17(12)11-7-10-3-6-15(21)23-14(10)8-13(11)20/h1-8,19-20H

InChI Key

GGNRJMYAXINNLX-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-hydroxycoumarins

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033559)
Cell membrane (HMDB: HMDB0033559)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033559)

Source

Exogenous

Exogenous (HMDB: HMDB0033559)

Food

Food (HMDB: HMDB0033559)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0033559)
Fabaceae (HMDB: HMDB0033559)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033559)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	293 - 294 °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	0.02 g/L	ALOGPS
logP	2.93	ALOGPS
logP	2.63	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	6.98	ChemAxon
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	86.14 m³·mol⁻¹	ChemAxon
Polarizability	31.02 Å³	ChemAxon
Number of Rings	4	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]+	173.229	31661259
DarkChem	[M-H]-	172.379	31661259
DeepCCS	[M+H]+	173.235	30932474
DeepCCS	[M-H]-	170.877	30932474
DeepCCS	[M-2H]-	204.601	30932474
DeepCCS	[M+Na]+	179.828	30932474
AllCCS	[M+H]+	173.6	32859911
AllCCS	[M+H-H2O]+	170.0	32859911
AllCCS	[M+NH4]+	176.9	32859911
AllCCS	[M+Na]+	177.9	32859911
AllCCS	[M-H]-	173.0	32859911
AllCCS	[M+Na-2H]-	171.9	32859911
AllCCS	[M+HCOO]-	170.9	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.	6.3 minutes	32390414
Predicted by Siyang on May 30, 2022	13.096 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	29.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1699.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	359.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	169.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	206.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	111.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	561.4 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	455.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	118.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	858.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	405.8 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	1519.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	357.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	335.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	358.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	259.9 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	89.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
7,7'-Dihydroxy-6,8'-bicoumarin	OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2	4180.1	Standard polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin	OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2	2636.7	Standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin	OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2	3421.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
7,7'-Dihydroxy-6,8'-bicoumarin,1TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2	3364.3	Semi standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C=CC(=O)OC2=C1C1=CC2=C(C=C1O)OC(=O)C=C2	3385.1	Semi standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O[Si](C)(C)C)C=CC2=C1OC(=O)C=C2	3320.7	Semi standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O)C=CC2=C1OC(=O)C=C2	3587.4	Semi standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC(=O)OC2=C1C1=CC2=C(C=C1O)OC(=O)C=C2	3610.0	Semi standard non polar	33892256
7,7'-Dihydroxy-6,8'-bicoumarin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=CC(=O)O2)C=C1C1=C(O[Si](C)(C)C(C)(C)C)C=CC2=C1OC(=O)C=C2	3795.2	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 - 7,7'-Dihydroxy-6,8'-bicoumarin GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-0090000000-204ac0c7ba0b50d55cab	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3005900000-6b2e72a2b62fac75bbc2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 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 - 7,7'-Dihydroxy-6,8'-bicoumarin 10V, Positive-QTOF	splash10-00di-0009000000-9a9116bb5617e95a9d90	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 20V, Positive-QTOF	splash10-00di-0059000000-1e1e17ecf98ff40bb1ff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 40V, Positive-QTOF	splash10-005i-0290000000-b61ae6546f6d98551d42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 10V, Negative-QTOF	splash10-00di-0039000000-d15da6fa8a69994ae55a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 20V, Negative-QTOF	splash10-00fr-0098000000-aa8f7f8e11e6f12cfb12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 40V, Negative-QTOF	splash10-0059-0090000000-ab6dbe37d4835948555f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 10V, Positive-QTOF	splash10-00di-0009000000-123f68ee6e11cc58e296	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 20V, Positive-QTOF	splash10-00dj-0079000000-33054d95ad6a7b6a4a71	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 40V, Positive-QTOF	splash10-002r-0090000000-7e67d35d3445c532b237	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 10V, Negative-QTOF	splash10-00di-0009000000-eed04c0fa05a4d9919f2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 20V, Negative-QTOF	splash10-00di-0019000000-ea76581b48f16fa50749	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 7,7'-Dihydroxy-6,8'-bicoumarin 40V, Negative-QTOF	splash10-00ou-0090000000-290281b6a596f75bb26b	2021-09-25	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

FDB011627

KNApSAcK ID

C00045682

Chemspider ID

10205904

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21588200

PDB ID

Not Available

ChEBI ID

Not Available

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

7,7'-Dihydroxy-6,8'-bicoumarin → 3,4,5-trihydroxy-6-({7-hydroxy-2H,2'H-[6,8'-bichromene]-2,2'-diyl}oxy)oxane-2-carboxylic acid	details
7,7'-Dihydroxy-6,8'-bicoumarin → 3,4,5-trihydroxy-6-({7'-hydroxy-2H,2'H-[6,8'-bichromene]-2,2'-diyl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 7,7'-Dihydroxy-6,8'-bicoumarin (HMDB0033559)

MOL for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

3D MOL for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

3D SDF for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

3D-SDF for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

PDB for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

3D PDB for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

SMILES for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

INCHI for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

Structure for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

3D Structure for HMDB0033559 (7,7'-Dihydroxy-6,8'-bicoumarin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions