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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:19:59 UTC

Update Date

2022-03-07 02:53:47 UTC

HMDB ID

HMDB0033588

Secondary Accession Numbers

HMDB33588

Metabolite Identification

Common Name

9-O-Methylcoumestrol

Description

9-O-Methylcoumestrol 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, 9-O-methylcoumestrol is considered to be a flavonoid. 9-O-Methylcoumestrol has been detected, but not quantified in, several different foods, such as green tea, common peas (Pisum sativum), green vegetables, chickpeas (Cicer arietinum), and alfalfas (Medicago sativa). This could make 9-O-methylcoumestrol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 9-O-Methylcoumestrol.

Structure

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

HMDB0033588
     RDKit          3D
9-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.3243    1.5761    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0210    0.3286    0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038   -0.0895   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4666   -1.3140   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1559   -1.7391   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -0.9440   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    0.2961    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    0.7121    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    0.8411    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    0.0382    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290    0.1449    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    1.2778    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395    1.3633    1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8432    0.3395    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    0.4932    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.7972    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373   -0.8741   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841   -1.9366   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867   -2.0669   -0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -3.0931   -1.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -1.0995   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    2.3994    0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3603    1.8899    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472    1.5588    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -1.9460   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -2.6769   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576    1.6725    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034    2.0632    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    2.2481    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    0.9386    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -1.6047   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8  3  1  0
 21 10  2  0
 21  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
M  END


  Mrv0541 05061307132D          

 21 24  0  0  0  0            999 V2000
   -1.9532    2.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2891    2.1084    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
    3.4655    2.0613    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
    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
    0.9407    3.1762    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
    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
    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
    1.6548    4.8202    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
    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
  4  2  2  0  0  0  0
  5  3  2  0  0  0  0
  8  2  1  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  1  0  0  0  0
 11  4  1  0  0  0  0
 12  6  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17  8  1  0  0  0  0
 18 16  2  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 20 13  1  0  0  0  0
 20 15  1  0  0  0  0
 21 12  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033588

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

> <INCHI_KEY>
HHEZPZWGHDOWCQ-UHFFFAOYSA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.2476

> <EXACT_MASS>
282.05282343

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.55305851630776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.85

> <JCHEM_LOGP>
2.543215378333333

> <ALOGPS_LOGS>
-3.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.115222554291015

> <JCHEM_PKA_STRONGEST_BASIC>
-4.223027562816092

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
74.1018

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033588
     RDKit          3D
9-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.3243    1.5761    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0210    0.3286    0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038   -0.0895   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4666   -1.3140   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1559   -1.7391   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -0.9440   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    0.2961    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    0.7121    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    0.8411    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    0.0382    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290    0.1449    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    1.2778    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395    1.3633    1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8432    0.3395    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    0.4932    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.7972    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373   -0.8741   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841   -1.9366   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867   -2.0669   -0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -3.0931   -1.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -1.0995   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    2.3994    0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3603    1.8899    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472    1.5588    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -1.9460   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -2.6769   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576    1.6725    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034    2.0632    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    2.2481    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    0.9386    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -1.6047   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8  3  1  0
 21 10  2  0
 21  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  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      -3.646   4.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.006   3.936   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       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.699   5.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.756   5.929   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.624   5.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.316   6.511   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.236   5.399   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.089   8.998   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.350   3.812   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   19                                                            
CONECT    2    4    8                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   10                                                       
CONECT    6    8   12                                                       
CONECT    7    9   13                                                       
CONECT    8    2    6   17                                                  
CONECT    9    3    7   19                                                  
CONECT   10    5   13   14                                                  
CONECT   11    4   12   15                                                  
CONECT   12    6   11   21                                                  
CONECT   13    7   10   20                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   20                                                  
CONECT   16   14   18   21                                                  
CONECT   17    8                                                            
CONECT   18   16                                                            
CONECT   19    1    9                                                       
CONECT   20   13   15                                                       
CONECT   21   12   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0033588
HETATM    1  C1  UNL     1      -5.324   1.576   0.710  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.021   0.329   0.114  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.704  -0.089  -0.019  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.467  -1.314  -0.607  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.156  -1.739  -0.745  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.141  -0.944  -0.300  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.374   0.296   0.295  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.676   0.712   0.429  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.228   0.841   0.625  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.740   0.038   0.283  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.129   0.145   0.411  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.684   1.278   0.996  1.00  0.00           C  
HETATM   13  C11 UNL     1       4.040   1.363   1.111  1.00  0.00           C  
HETATM   14  C12 UNL     1       4.843   0.340   0.653  1.00  0.00           C  
HETATM   15  O3  UNL     1       6.236   0.493   0.803  1.00  0.00           O  
HETATM   16  C13 UNL     1       4.330  -0.797   0.067  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.937  -0.874  -0.045  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.384  -1.937  -0.596  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.087  -2.067  -0.730  1.00  0.00           C  
HETATM   20  O5  UNL     1       0.574  -3.093  -1.261  1.00  0.00           O  
HETATM   21  C16 UNL     1       0.230  -1.100  -0.302  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.670   2.399   0.298  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.360   1.890   0.458  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.147   1.559   1.799  1.00  0.00           H  
HETATM   25  H4  UNL     1      -4.270  -1.946  -0.960  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.933  -2.677  -1.193  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.858   1.672   0.890  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.003   2.063   1.344  1.00  0.00           H  
HETATM   29  H8  UNL     1       4.459   2.248   1.568  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.705   0.939   0.036  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.948  -1.605  -0.295  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   21
CONECT    7    8    8    9
CONECT    8   27
CONECT    9   10
CONECT   10   11   21   21
CONECT   11   12   12   17
CONECT   12   13   28
CONECT   13   14   14   29
CONECT   14   15   16
CONECT   15   30
CONECT   16   17   17   31
CONECT   17   18
CONECT   18   19
CONECT   19   20   20   21
END

HMDB0033588
     RDKit          3D
9-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.3243    1.5761    0.7097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0210    0.3286    0.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7038   -0.0895   -0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4666   -1.3140   -0.6071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1559   -1.7391   -0.7447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1407   -0.9440   -0.3000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3739    0.2961    0.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6761    0.7121    0.4291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2282    0.8411    0.6246 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7397    0.0382    0.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1290    0.1449    0.4106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6838    1.2778    0.9960 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0395    1.3633    1.1112 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8432    0.3395    0.6526 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2361    0.4932    0.8032 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3296   -0.7972    0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373   -0.8741   -0.0455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3841   -1.9366   -0.5964 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0867   -2.0669   -0.7303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5742   -3.0931   -1.2612 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2299   -1.0995   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6695    2.3994    0.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3603    1.8899    0.4582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1472    1.5588    1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2701   -1.9460   -0.9604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9327   -2.6769   -1.1925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8576    1.6725    0.8902 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0034    2.0632    1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    2.2481    1.5677 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    0.9386    0.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9481   -1.6047   -0.2951 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
  8  3  1  0
 21 10  2  0
 21  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 12 28  1  0
 13 29  1  0
 15 30  1  0
 16 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-O-Methylcoumestrol	HMDB
3-Hydroxy-9-methoxycoumestan	HMDB
4'-Methoxycoumestrol	HMDB
4'-O-Methylcoumestrol	HMDB
Methyl N-methylnipecotate	HMDB

Chemical Formula

C₁₆H₁₀O₅

Average Molecular Weight

282.2476

Monoisotopic Molecular Weight

282.05282343

IUPAC Name

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

Traditional Name

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

CAS Registry Number

1690-62-6

SMILES

COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2

InChI Identifier

InChI=1S/C16H10O5/c1-19-9-3-5-10-13(7-9)20-15-11-4-2-8(17)6-12(11)21-16(18)14(10)15/h2-7,17H,1H3

InChI Key

HHEZPZWGHDOWCQ-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
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Furan
Lactone
Organoheterocyclic compound
Oxacycle
Ether
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Coumestan flavonoids (LMPK12090019 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033588)
Cell membrane (HMDB: HMDB0033588)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033588)

Source

Exogenous

Exogenous (HMDB: HMDB0033588)

Food

Food (HMDB: HMDB0033588)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pea

Chickpea (FooDB: FOOD00047)
Common pea (FooDB: FOOD00141)

Pulses (FooDB: FOOD00867)

Tea

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0033588)
Fabaceae (HMDB: HMDB0033588)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033588)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	338 - 339 °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	0.11 g/L	ALOGPS
logP	2.85	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	68.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.1 m³·mol⁻¹	ChemAxon
Polarizability	28.55 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]+	165.434	31661259
DarkChem	[M-H]-	166.999	31661259
DeepCCS	[M+H]+	172.963	30932474
DeepCCS	[M-H]-	170.605	30932474
DeepCCS	[M-2H]-	204.212	30932474
DeepCCS	[M+Na]+	179.439	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.7	32859911
AllCCS	[M+NH4]+	167.1	32859911
AllCCS	[M+Na]+	168.1	32859911
AllCCS	[M-H]-	166.0	32859911
AllCCS	[M+Na-2H]-	164.9	32859911
AllCCS	[M+HCOO]-	163.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	4011.9	Standard polar	33892256
9-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	2830.5	Standard non polar	33892256
9-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(O2)C2=C(OC1=O)C=C(O)C=C2	2944.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-O-Methylcoumestrol,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C21	3029.3	Semi standard non polar	33892256
9-O-Methylcoumestrol,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3232.1	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 - 9-O-Methylcoumestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f80-0190000000-94c11589b4285910e5d8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-O-Methylcoumestrol GC-MS (1 TMS) - 70eV, Positive	splash10-0g5i-4779000000-921bc270bf36e4137802	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9-O-Methylcoumestrol 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 - 9-O-Methylcoumestrol 10V, Positive-QTOF	splash10-001i-0090000000-1ff7411520d6ff0f22e6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 20V, Positive-QTOF	splash10-001i-0090000000-dcbe2788c89b14ce9a8d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 40V, Positive-QTOF	splash10-0gdi-0090000000-7c3dc506068d21eb5b43	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 10V, Negative-QTOF	splash10-001i-0090000000-bf271b4239f9685356ef	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 20V, Negative-QTOF	splash10-001i-0090000000-76e8557afe95a6a46488	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 40V, Negative-QTOF	splash10-014i-1090000000-9989e1a4f1e55a6c4f62	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 10V, Positive-QTOF	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 20V, Positive-QTOF	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 40V, Positive-QTOF	splash10-053v-0190000000-fece2d85dbb0fd2da10b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 10V, Negative-QTOF	splash10-001i-0090000000-60166d79143e3c19fb0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 20V, Negative-QTOF	splash10-001i-0090000000-cab7882440e1204f1c6e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-O-Methylcoumestrol 40V, Negative-QTOF	splash10-0gbi-0090000000-9531507e13c5ce98799b	2021-09-24	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

FDB011665

KNApSAcK ID

C00009757

Chemspider ID

4477838

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16800

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1836921

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

9-O-Methylcoumestrol → 3,4,5-trihydroxy-6-({14-methoxy-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 9-O-Methylcoumestrol (HMDB0033588)

MOL for HMDB0033588 (9-O-Methylcoumestrol)

3D MOL for HMDB0033588 (9-O-Methylcoumestrol)

3D SDF for HMDB0033588 (9-O-Methylcoumestrol)

3D-SDF for HMDB0033588 (9-O-Methylcoumestrol)

PDB for HMDB0033588 (9-O-Methylcoumestrol)

3D PDB for HMDB0033588 (9-O-Methylcoumestrol)

SMILES for HMDB0033588 (9-O-Methylcoumestrol)

INCHI for HMDB0033588 (9-O-Methylcoumestrol)

Structure for HMDB0033588 (9-O-Methylcoumestrol)

3D Structure for HMDB0033588 (9-O-Methylcoumestrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions