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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002326

Secondary Accession Numbers

HMDB02326

Metabolite Identification

Common Name

Coumesterol

Description

Cumoesterol (or coumestrol), a coumestan isoflavone, has estrogenic properties (phytoestrogens are compounds structurally and functionally similar to 17-estradiol) and is an isoflavonoid phytoalexin produced by soybeans, a low molecular weight antimicrobial compound that is synthesized de novo and accumulates in plants after exposure to microorganisms (i.e.: phytoalexin induction and accumulation in soybean cotyledon tissue is observed with four species of Aspergillus: A. sojae, A. oryzae, A. niger, and A. flavus) (PMID: 10888516 ). Coumestrol is a naturally occurring plant coumarin that displays high affinity for the hormone-binding site of the human estrogen receptor (hER), for which it serves as a potent non-steroidal agonist. Coumestrol emits intense blue fluorescence when bound to this protein, making it ideally suited for use as a cytological stain to detect ER in fixed and intact cells. Such observations illustrate the potential for using coumestrol to investigate real-time effects of a variety of physiological stimuli on the subcellular distribution of hER in living cells (PMID: 8315272 ).

Structure

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

HMDB0002326
     RDKit          3D
Coumesterol
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.6047   -0.5513    2.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395   -0.3064    1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -0.2614    2.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    0.0000    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736    0.0434    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    0.3134    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742    0.3508    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.5501   -1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    0.5146   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.2414   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667    0.2000   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    0.3817   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    0.2445   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    0.3315   -1.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    0.1240   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647    0.2157   -1.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990   -0.1633    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622   -0.2444    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -0.0453    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848   -0.0760    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.1476    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1751    0.1698    1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    0.7681   -2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.6969   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    0.5571   -2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.0760   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -0.3232    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221   -0.4698    2.0965 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  2  0
 19 20  1  0
 20  2  1  0
 10  4  1  0
 20 11  2  0
 19 13  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
M  END

Coumestrol
  Mrv1572001071617322D          

 20 23  0  0  0  0            999 V2000
    5.8101    1.1687    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0768    0.7906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3828    1.2366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6495    0.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6103    0.0344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3043   -0.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0376   -0.0335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8144   -0.1829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3618    0.5068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8779    1.1504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5381    0.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1671   -0.2772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6198   -0.9670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4434   -0.9198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8961   -1.6095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3435   -0.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1092    0.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2618    1.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0855    1.1494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 11 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002326

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H

> <INCHI_KEY>
ZZIALNLLNHEQPJ-UHFFFAOYSA-N

> <FORMULA>
C15H8O5

> <MOLECULAR_WEIGHT>
268.224

> <EXACT_MASS>
268.037173358

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
26.40531448424779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,14-dihydroxy-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>
2.43

> <JCHEM_LOGP>
2.3973213223333327

> <ALOGPS_LOGS>
-2.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.111552628222421

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.110949661336945

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0531035874613637

> <JCHEM_POLAR_SURFACE_AREA>
79.9

> <JCHEM_REFRACTIVITY>
69.6195

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coumestrol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002326
     RDKit          3D
Coumesterol
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.6047   -0.5513    2.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395   -0.3064    1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -0.2614    2.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    0.0000    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736    0.0434    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    0.3134    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742    0.3508    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.5501   -1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    0.5146   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.2414   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667    0.2000   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    0.3817   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    0.2445   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    0.3315   -1.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    0.1240   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647    0.2157   -1.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990   -0.1633    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622   -0.2444    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -0.0453    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848   -0.0760    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.1476    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1751    0.1698    1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    0.7681   -2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.6969   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    0.5571   -2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.0760   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -0.3232    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221   -0.4698    2.0965 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  2  0
 19 20  1  0
 20  2  1  0
 10  4  1  0
 20 11  2  0
 19 13  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Coumestrol                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  O   UNK     0      10.846   2.182   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       9.477   1.476   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.181   2.308   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.812   1.603   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.739   0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.035  -0.768   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.404  -0.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.254  -0.341   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.409   0.946   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.372   2.147   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.871   0.858   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.179  -0.517   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.024  -1.805   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.561  -1.717   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.406  -3.004   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.641  -0.606   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.204   0.682   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.741   0.594   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.489   2.057   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.026   2.146   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9   12   20                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16   12   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   11                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0002326
HETATM    1  O1  UNL     1       0.605  -0.551   2.981  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.139  -0.306   1.997  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.442  -0.261   2.069  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.191   0.000   1.008  1.00  0.00           C  
HETATM    5  C3  UNL     1      -3.574   0.043   1.105  1.00  0.00           C  
HETATM    6  C4  UNL     1      -4.383   0.313   0.018  1.00  0.00           C  
HETATM    7  O3  UNL     1      -5.774   0.351   0.144  1.00  0.00           O  
HETATM    8  C5  UNL     1      -3.819   0.550  -1.212  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.433   0.515  -1.346  1.00  0.00           C  
HETATM   10  C7  UNL     1      -1.651   0.241  -0.238  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.267   0.200  -0.345  1.00  0.00           C  
HETATM   12  O4  UNL     1       0.524   0.382  -1.366  1.00  0.00           O  
HETATM   13  C9  UNL     1       1.782   0.245  -0.997  1.00  0.00           C  
HETATM   14  C10 UNL     1       3.002   0.332  -1.669  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.171   0.124  -0.952  1.00  0.00           C  
HETATM   16  O5  UNL     1       5.365   0.216  -1.640  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.199  -0.163   0.386  1.00  0.00           C  
HETATM   18  C13 UNL     1       2.962  -0.244   1.034  1.00  0.00           C  
HETATM   19  C14 UNL     1       1.795  -0.045   0.356  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.485  -0.076   0.784  1.00  0.00           C  
HETATM   21  H1  UNL     1      -4.001  -0.148   2.091  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.175   0.170   1.078  1.00  0.00           H  
HETATM   23  H3  UNL     1      -4.379   0.768  -2.110  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.953   0.697  -2.303  1.00  0.00           H  
HETATM   25  H5  UNL     1       2.989   0.557  -2.721  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.264   0.076  -1.181  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.117  -0.323   0.935  1.00  0.00           H  
HETATM   28  H8  UNL     1       2.922  -0.470   2.097  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   20
CONECT    3    4
CONECT    4    5    5   10
CONECT    5    6   21
CONECT    6    7    8    8
CONECT    7   22
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11
CONECT   11   12   20   20
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   25
CONECT   15   16   17   17
CONECT   16   26
CONECT   17   18   27
CONECT   18   19   19   28
CONECT   19   20
END

HMDB0002326
     RDKit          3D
Coumesterol
 28 31  0  0  0  0  0  0  0  0999 V2000
    0.6047   -0.5513    2.9808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1395   -0.3064    1.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4420   -0.2614    2.0688 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1909    0.0000    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736    0.0434    1.1053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3827    0.3134    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7742    0.3508    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8188    0.5501   -1.2121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4329    0.5146   -1.3464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6509    0.2414   -0.2382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2667    0.2000   -0.3448 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5236    0.3817   -1.3660 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7818    0.2445   -0.9974 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0021    0.3315   -1.6691 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1706    0.1240   -0.9519 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647    0.2157   -1.6396 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1990   -0.1633    0.3861 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9622   -0.2444    1.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7952   -0.0453    0.3556 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4848   -0.0760    0.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.1476    2.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1751    0.1698    1.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3790    0.7681   -2.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9530    0.6969   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9886    0.5571   -2.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2636    0.0760   -1.1814 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1171   -0.3232    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9221   -0.4698    2.0965 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  2  0
 19 20  1  0
 20  2  1  0
 10  4  1  0
 20 11  2  0
 19 13  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
  9 24  1  0
 14 25  1  0
 16 26  1  0
 17 27  1  0
 18 28  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,9-Dihydroxycoumestan	ChEBI
Chrysanthin	ChEBI
3,9-Dihydroxy-6H-[1]benzofuro[3,2-c]chromen-6-one	HMDB
Coumestrol	HMDB
Cumoesterol	HMDB

Chemical Formula

C₁₅H₈O₅

Average Molecular Weight

268.224

Monoisotopic Molecular Weight

268.037173358

IUPAC Name

5,14-dihydroxy-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

coumestrol

CAS Registry Number

479-13-0

SMILES

OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

InChI Identifier

InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H

InChI Key

ZZIALNLLNHEQPJ-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-2-unsubstituted benzenoid
Pyranone
Pyran
Benzenoid
Furan
Heteroaromatic compound
Lactone
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:3908 )
delta-lactone (CHEBI:3908 )
coumestans (CHEBI:3908 )
Coumestan flavonoids (C10205 )
Coumestanes (C10205 )
Coumestan flavonoids (LMPK12090018 )
an isoflavone (CPD-11779 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	385 °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	0.28 g/L	ALOGPS
logP	2.43	ALOGPS
logP	2.4	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	79.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.62 m³·mol⁻¹	ChemAxon
Polarizability	26.41 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]+	159.43	31661259
DarkChem	[M-H]-	159.972	31661259
DeepCCS	[M+H]+	166.464	30932474
DeepCCS	[M-H]-	164.106	30932474
DeepCCS	[M-2H]-	197.412	30932474
DeepCCS	[M+Na]+	172.639	30932474
AllCCS	[M+H]+	159.6	32859911
AllCCS	[M+H-H2O]+	155.6	32859911
AllCCS	[M+NH4]+	163.2	32859911
AllCCS	[M+Na]+	164.3	32859911
AllCCS	[M-H]-	160.9	32859911
AllCCS	[M+Na-2H]-	159.8	32859911
AllCCS	[M+HCOO]-	158.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Coumesterol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	4089.1	Standard polar	33892256
Coumesterol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	2667.5	Standard non polar	33892256
Coumesterol	OC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	3019.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Coumesterol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	2967.4	Semi standard non polar	33892256
Coumesterol,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	2991.1	Semi standard non polar	33892256
Coumesterol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3131.2	Semi standard non polar	33892256
Coumesterol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O)=CC=C21	3171.8	Semi standard non polar	33892256
Coumesterol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O)=CC=C21	3194.9	Semi standard non polar	33892256
Coumesterol,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=C21	3556.6	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 - Coumesterol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00rf-0090000000-24d398554cf83008a0b2	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumesterol GC-MS (2 TMS) - 70eV, Positive	splash10-00di-3029000000-09e31fd7995c1524643c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Coumesterol 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 20V, Negative-QTOF	splash10-014i-0090000000-3b007f8a59433c8c8102	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 10V, Negative-QTOF	splash10-014i-0090000000-3b007f8a59433c8c8102	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-5a91822fb14572c010a0	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 40V, Negative-QTOF	splash10-014i-0290000000-75cc1c58769101835d99	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 10V, Negative-QTOF	splash10-014i-0290000000-75cc1c58769101835d99	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 50V, Negative-QTOF	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 20V, Negative-QTOF	splash10-014i-0090000000-2a1a393fb92c1f28256e	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 10V, Negative-QTOF	splash10-014i-0090000000-606e78910a0367fb9798	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-5a91822fb14572c010a0	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 40V, Negative-QTOF	splash10-014i-0290000000-75cc1c58769101835d99	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 10V, Negative-QTOF	splash10-014i-0090000000-895c91406544dc79d34d	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol ESI-TOF 50V, Negative-QTOF	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-qTof , Positive-QTOF	splash10-0904-3940000000-5bc2aef444fc6910fc19	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol Linear Ion Trap , negative-QTOF	splash10-014i-0090000000-9fa59481d26b0a93d7c8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-TOF , negative-QTOF	splash10-014i-0090000000-2a1a393fb92c1f28256e	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-TOF , negative-QTOF	splash10-014i-0090000000-606e78910a0367fb9798	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-TOF , negative-QTOF	splash10-014i-0090000000-5a91822fb14572c010a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-TOF , negative-QTOF	splash10-014i-0290000000-75cc1c58769101835d99	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Coumesterol LC-ESI-TOF , negative-QTOF	splash10-0159-0960010000-fe04b8935dfef822b8ba	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 10V, Positive-QTOF	splash10-014i-0090000000-121d9805507777b81a75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 20V, Positive-QTOF	splash10-014i-0090000000-b99e1506236f0fb0601d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 40V, Positive-QTOF	splash10-004i-1490000000-9ba6d9042addda981b5b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 10V, Negative-QTOF	splash10-014i-0090000000-a481cda3a4b436df23dd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 20V, Negative-QTOF	splash10-014i-0090000000-3606deabc4ddf6ecce16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Coumesterol 40V, Negative-QTOF	splash10-00di-0390000000-71b617f0a4545c7f72cc	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0123 +/- 0.0123 uM	Adult (>18 years old)	Both	Normal	17490695	details
Urine	Detected and Quantified	0.000160 +/- 0.000800 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.00480 +/- 0.0144 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0208 +/- 0.112 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	9681530	details
Urine	Detected and Quantified	0.0081 (0.0033-0.0120) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 399	10952094	details

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Coumestrol

METLIN ID

Not Available

PubChem Compound

5281707

PDB ID

Not Available

ChEBI ID

3908

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Kappe, Thomas; Brandner, Alexander. Simple synthesis of coumestrol. Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, Biochemie, Biophysik, Biologie (1974), 29(3-4), 292-3.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Boue SM, Carter CH, Ehrlich KC, Cleveland TE: Induction of the soybean phytoalexins coumestrol and glyceollin by Aspergillus. J Agric Food Chem. 2000 Jun;48(6):2167-72. [PubMed:10888516 ]
Miksicek RJ: In situ localization of the estrogen receptor in living cells with the fluorescent phytoestrogen coumestrol. J Histochem Cytochem. 1993 Jun;41(6):801-10. [PubMed:8315272 ]

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

Coumesterol → 3,4,5-trihydroxy-6-({5-hydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-14-yl}oxy)oxane-2-carboxylic acid	details
Coumesterol → 3,4,5-trihydroxy-6-({14-hydroxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-5-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for Coumesterol (HMDB0002326)

MOL for HMDB0002326 (Coumesterol)

3D MOL for HMDB0002326 (Coumesterol)

3D SDF for HMDB0002326 (Coumesterol)

3D-SDF for HMDB0002326 (Coumesterol)

PDB for HMDB0002326 (Coumesterol)

3D PDB for HMDB0002326 (Coumesterol)

SMILES for HMDB0002326 (Coumesterol)

INCHI for HMDB0002326 (Coumesterol)

Structure for HMDB0002326 (Coumesterol)

3D Structure for HMDB0002326 (Coumesterol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions