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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:56:01 UTC

Update Date

2022-03-07 02:54:00 UTC

HMDB ID

HMDB0034138

Secondary Accession Numbers

HMDB34138

Metabolite Identification

Common Name

Repensol

Description

Repensol belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Thus, repensol is considered to be a flavonoid. Repensol has been detected, but not quantified in, several different foods, such as green tea, teas (Camellia sinensis), red tea, herbs and spices, and black tea. This could make repensol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Repensol.

Structure

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

HMDB0034138
     RDKit          3D
Repensol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.7983   -2.8928    0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.9376    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -2.1552    0.6923 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321   -1.1708    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.4182    1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3454    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6135   -0.5759    1.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136    0.9354    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159    1.1604    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    0.1150    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.3698   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1985    1.4787   -0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    1.2028   -0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407    1.9430   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.3976   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    2.1616   -1.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    0.0301   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696   -0.7420   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -2.0870   -0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.1482   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.7022   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -2.4274    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -0.8181    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001    1.7784    0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    2.1489    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191    3.0152   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4896    2.6254   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9026   -0.4337   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9761   -2.5079   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21  2  1  0
 10  4  1  0
 21 11  2  0
 20 13  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END


  Mrv0541 05061307362D          

 21 24  0  0  0  0            999 V2000
    4.2891    2.1084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    2.0613    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4867    3.2441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2075    3.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    1.9741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6601    2.8453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5259    2.4201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0128    2.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2466    3.6222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3838    3.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9014    2.3522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9407    3.1762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7365    3.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1892    2.7039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075    4.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838    2.8924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2591    2.0420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2858    4.4463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    4.8202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6731    2.0602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9312    4.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  6  1  1  0  0  0  0
  6  4  2  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  4  1  0  0  0  0
 10  8  2  0  0  0  0
 11  5  2  0  0  0  0
 12  9  2  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15 13  1  0  0  0  0
 16  6  1  0  0  0  0
 17  7  1  0  0  0  0
 18  9  1  0  0  0  0
 19 15  2  0  0  0  0
 20 11  1  0  0  0  0
 20 14  1  0  0  0  0
 21 10  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034138

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)21-15(19)13-12-9(18)3-7(17)5-11(12)20-14(8)13/h1-5,16-18H

> <INCHI_KEY>
CFUAZBGEKBTCSH-UHFFFAOYSA-N

> <FORMULA>
C15H8O6

> <MOLECULAR_WEIGHT>
284.2204

> <EXACT_MASS>
284.032087988

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
27.244056714381358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.0937560006666662

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
7.940014865035821

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.071419585310014

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9182363982868913

> <JCHEM_POLAR_SURFACE_AREA>
100.13

> <JCHEM_REFRACTIVITY>
71.6004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034138
     RDKit          3D
Repensol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.7983   -2.8928    0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.9376    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -2.1552    0.6923 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321   -1.1708    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.4182    1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3454    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6135   -0.5759    1.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136    0.9354    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159    1.1604    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    0.1150    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.3698   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1985    1.4787   -0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    1.2028   -0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407    1.9430   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.3976   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    2.1616   -1.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    0.0301   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696   -0.7420   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -2.0870   -0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.1482   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.7022   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -2.4274    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -0.8181    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001    1.7784    0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    2.1489    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191    3.0152   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4896    2.6254   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9026   -0.4337   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9761   -2.5079   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21  2  1  0
 10  4  1  0
 21 11  2  0
 20 13  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  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       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.533   8.300   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    8                                                       
CONECT    3    7    9                                                       
CONECT    4    6   10                                                       
CONECT    5    7   11                                                       
CONECT    6    1    4   16                                                  
CONECT    7    3    5   17                                                  
CONECT    8    2   10   14                                                  
CONECT    9    3   12   18                                                  
CONECT   10    4    8   21                                                  
CONECT   11    5   12   20                                                  
CONECT   12    9   11   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14    8   13   20                                                  
CONECT   15   13   19   21                                                  
CONECT   16    6                                                            
CONECT   17    7                                                            
CONECT   18    9                                                            
CONECT   19   15                                                            
CONECT   20   11   14                                                       
CONECT   21   10   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0034138
HETATM    1  O1  UNL     1      -0.798  -2.893   0.284  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.031  -1.938   0.322  1.00  0.00           C  
HETATM    3  O2  UNL     1       1.281  -2.155   0.692  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.132  -1.171   0.730  1.00  0.00           C  
HETATM    5  C3  UNL     1       3.454  -1.418   1.125  1.00  0.00           C  
HETATM    6  C4  UNL     1       4.295  -0.345   1.144  1.00  0.00           C  
HETATM    7  O3  UNL     1       5.614  -0.576   1.534  1.00  0.00           O  
HETATM    8  C5  UNL     1       3.914   0.935   0.802  1.00  0.00           C  
HETATM    9  C6  UNL     1       2.616   1.160   0.418  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.735   0.115   0.383  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.437   0.370  -0.007  1.00  0.00           C  
HETATM   12  O4  UNL     1      -0.199   1.479  -0.383  1.00  0.00           O  
HETATM   13  C9  UNL     1      -1.451   1.203  -0.661  1.00  0.00           C  
HETATM   14  C10 UNL     1      -2.541   1.943  -1.087  1.00  0.00           C  
HETATM   15  C11 UNL     1      -3.783   1.398  -1.311  1.00  0.00           C  
HETATM   16  O5  UNL     1      -4.844   2.162  -1.735  1.00  0.00           O  
HETATM   17  C12 UNL     1      -3.930   0.030  -1.092  1.00  0.00           C  
HETATM   18  C13 UNL     1      -2.870  -0.742  -0.667  1.00  0.00           C  
HETATM   19  O6  UNL     1      -3.096  -2.087  -0.473  1.00  0.00           O  
HETATM   20  C14 UNL     1      -1.643  -0.148  -0.456  1.00  0.00           C  
HETATM   21  C15 UNL     1      -0.432  -0.702  -0.033  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.719  -2.427   1.385  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.298  -0.818   0.812  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.600   1.778   0.823  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.248   2.149   0.134  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.419   3.015  -1.258  1.00  0.00           H  
HETATM   27  H6  UNL     1      -5.490   2.625  -1.097  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.903  -0.434  -1.260  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.976  -2.508  -0.625  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   21
CONECT    3    4
CONECT    4    5    5   10
CONECT    5    6   22
CONECT    6    7    8    8
CONECT    7   23
CONECT    8    9   24
CONECT    9   10   10   25
CONECT   10   11
CONECT   11   12   21   21
CONECT   12   13
CONECT   13   14   14   20
CONECT   14   15   26
CONECT   15   16   17   17
CONECT   16   27
CONECT   17   18   28
CONECT   18   19   20   20
CONECT   19   29
CONECT   20   21
END

HMDB0034138
     RDKit          3D
Repensol
 29 32  0  0  0  0  0  0  0  0999 V2000
   -0.7983   -2.8928    0.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0312   -1.9376    0.3222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2815   -2.1552    0.6923 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1321   -1.1708    0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4545   -1.4182    1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2950   -0.3454    1.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6135   -0.5759    1.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9136    0.9354    0.8016 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159    1.1604    0.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7349    0.1150    0.3831 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4368    0.3698   -0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1985    1.4787   -0.3833 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4512    1.2028   -0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5407    1.9430   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7829    1.3976   -1.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8444    2.1616   -1.7350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9301    0.0301   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8696   -0.7420   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0958   -2.0870   -0.4727 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.1482   -0.4564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325   -0.7022   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7193   -2.4274    1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2982   -0.8181    0.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6001    1.7784    0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2481    2.1489    0.1342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4191    3.0152   -1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4896    2.6254   -1.0969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9026   -0.4337   -1.2603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9761   -2.5079   -0.6249 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 21  2  1  0
 10  4  1  0
 21 11  2  0
 20 13  1  0
  5 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
 14 26  1  0
 16 27  1  0
 17 28  1  0
 19 29  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,7,9-Trihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one, 9ci	HMDB
7,10,12-Trihydroxycoumestan	HMDB
Repensol3,7,9-trihydroxycoumestan	HMDB

Chemical Formula

C₁₅H₈O₆

Average Molecular Weight

284.2204

Monoisotopic Molecular Weight

284.032087988

IUPAC Name

5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

Traditional Name

5,12,14-trihydroxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one

CAS Registry Number

33280-69-2

SMILES

OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2

InChI Identifier

InChI=1S/C15H8O6/c16-6-1-2-8-10(4-6)21-15(19)13-12-9(18)3-7(17)5-11(12)20-14(8)13/h1-5,16-18H

InChI Key

CFUAZBGEKBTCSH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Coumestans

Direct Parent

Coumestans

Alternative Parents

Substituents

Coumestan
Angular furanocoumarin
Furanocoumarin
Coumarin
Benzopyran
1-benzopyran
Benzofuran
Furopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Polyol
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090029 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034138)
Cell membrane (HMDB: HMDB0034138)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034138)

Source

Exogenous

Exogenous (HMDB: HMDB0034138)

Food

Food (HMDB: HMDB0034138)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034138)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034138)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	346 - 348 °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	0.91 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.09	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	7.07	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	71.6 m³·mol⁻¹	ChemAxon
Polarizability	27.24 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]+	161.77	31661259
DarkChem	[M-H]-	164.113	31661259
DeepCCS	[M+H]+	167.51	30932474
DeepCCS	[M-H]-	165.152	30932474
DeepCCS	[M-2H]-	198.319	30932474
DeepCCS	[M+Na]+	173.603	30932474
AllCCS	[M+H]+	163.0	32859911
AllCCS	[M+H-H2O]+	159.2	32859911
AllCCS	[M+NH4]+	166.5	32859911
AllCCS	[M+Na]+	167.5	32859911
AllCCS	[M-H]-	163.3	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	161.1	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. Predicted by Afia on May 17, 2022.	5.84 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6913 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2140.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	156.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	234.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	380.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	588.3 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	525.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	83.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1108.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	427.6 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	1535.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	389.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	439.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	242.1 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	150.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Repensol	OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2	4598.2	Standard polar	33892256
Repensol	OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2	2534.9	Standard non polar	33892256
Repensol	OC1=CC2=C(C=C1)C1=C(C3=C(O)C=C(O)C=C3O1)C(=O)O2	3159.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Repensol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O)=C21	3165.9	Semi standard non polar	33892256
Repensol,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(O2)C2=CC=C(O)C=C2OC1=O	3113.4	Semi standard non polar	33892256
Repensol,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3134.2	Semi standard non polar	33892256
Repensol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC(O)=C21	3240.0	Semi standard non polar	33892256
Repensol,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O[Si](C)(C)C)=C21	3175.4	Semi standard non polar	33892256
Repensol,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3147.2	Semi standard non polar	33892256
Repensol,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C21	3299.6	Semi standard non polar	33892256
Repensol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O)=C21	3383.1	Semi standard non polar	33892256
Repensol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C1=C(O2)C2=CC=C(O)C=C2OC1=O	3314.4	Semi standard non polar	33892256
Repensol,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3350.7	Semi standard non polar	33892256
Repensol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C21	3679.9	Semi standard non polar	33892256
Repensol,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C21	3615.9	Semi standard non polar	33892256
Repensol,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3579.2	Semi standard non polar	33892256
Repensol,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C21	3947.9	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 - Repensol GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-0090000000-02879d089d9526293c3c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repensol GC-MS (3 TMS) - 70eV, Positive	splash10-00bi-3001900000-447c045c9fbf2a9b6dab	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repensol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Repensol 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 - Repensol 10V, Positive-QTOF	splash10-000i-0090000000-9be28a959ef0b37d8bc8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 20V, Positive-QTOF	splash10-000i-0090000000-0e33bfa58857dae13e6e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 40V, Positive-QTOF	splash10-014l-1190000000-a5b6bb1b5f294453f38d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 10V, Negative-QTOF	splash10-001i-0090000000-91aee8e36c5014083645	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 20V, Negative-QTOF	splash10-001i-0090000000-d1f47f392c533df77377	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 40V, Negative-QTOF	splash10-000i-0290000000-4a1c98a40450b17a81e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 10V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 20V, Positive-QTOF	splash10-000i-0090000000-3896d645ce486a1e32ca	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 40V, Positive-QTOF	splash10-0a4l-0090000000-86d2b3afdb851de8274a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 10V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 20V, Negative-QTOF	splash10-001i-0090000000-279002154c712db975df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Repensol 40V, Negative-QTOF	splash10-03gi-0090000000-8b7db004d7c35df3ff90	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

FDB012413

KNApSAcK ID

C00009758

Chemspider ID

24843113

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257533

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

Repensol → 6-({5,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-12-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Repensol → 6-({5,12-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Repensol → 6-({12,14-dihydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for Repensol (HMDB0034138)

MOL for HMDB0034138 (Repensol)

3D MOL for HMDB0034138 (Repensol)

3D SDF for HMDB0034138 (Repensol)

3D-SDF for HMDB0034138 (Repensol)

PDB for HMDB0034138 (Repensol)

3D PDB for HMDB0034138 (Repensol)

SMILES for HMDB0034138 (Repensol)

INCHI for HMDB0034138 (Repensol)

Structure for HMDB0034138 (Repensol)

3D Structure for HMDB0034138 (Repensol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions