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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:17 UTC

Update Date

2022-03-07 02:52:13 UTC

HMDB ID

HMDB0029584

Secondary Accession Numbers

HMDB29584

Metabolite Identification

Common Name

3-O-Methylcoumestrol

Description

3-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. 3-O-Methylcoumestrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-O-methylcoumestrol has been detected, but not quantified in, pulses. This could make 3-O-methylcoumestrol a potential biomarker for the consumption of these foods.

Structure

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

HMDB0029584
     RDKit          3D
3-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.8384   -0.6530    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0041   -0.1599    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -0.1115    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    0.3753    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4630    0.4586    1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    0.0422    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386   -0.4487   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184   -0.5161   -0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243   -0.8538   -1.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705   -0.8117   -1.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -1.2172   -2.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -0.3366   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -0.1732   -0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3842   -0.4357   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796   -0.1626   -1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    0.3635    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2483    0.6298    0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9071    0.6154    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769    0.3504    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5030    1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.0961    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4322   -1.5784   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.7498    0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8244    0.1120   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7032    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.8404    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222   -0.8983   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395   -0.8505   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.3698   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7749   -0.0956    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461    1.0275    1.8582 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  2  0
 21  6  1  0
 19 13  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END


  Mrv0541 05061304492D          

 21 24  0  0  0  0            999 V2000
    5.8548    3.6293    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
    4.2891    2.1084    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
    3.4655    2.0613    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
    4.2075    3.5350    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
    4.6601    2.8453    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
    0.9014    2.3522    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
    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
   -1.2591    2.0420    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
    5.4838    2.8924    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  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  7  1  0  0  0  0
 13 11  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 12  1  0  0  0  0
 20 15  1  0  0  0  0
 21 13  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029584

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2

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

> <INCHI_KEY>
YQBVKPREVBFWSA-UHFFFAOYSA-N

> <FORMULA>
C16H10O5

> <MOLECULAR_WEIGHT>
282.2476

> <EXACT_MASS>
282.05282343

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
28.562114116365922

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
14-hydroxy-5-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>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.106855157944299

> <JCHEM_PKA_STRONGEST_BASIC>
-4.209048569217263

> <JCHEM_POLAR_SURFACE_AREA>
68.9

> <JCHEM_REFRACTIVITY>
74.1018

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
14-hydroxy-5-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

$$$$

HMDB0029584
     RDKit          3D
3-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.8384   -0.6530    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0041   -0.1599    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -0.1115    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    0.3753    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4630    0.4586    1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    0.0422    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386   -0.4487   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184   -0.5161   -0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243   -0.8538   -1.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705   -0.8117   -1.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -1.2172   -2.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -0.3366   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -0.1732   -0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3842   -0.4357   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796   -0.1626   -1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    0.3635    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2483    0.6298    0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9071    0.6154    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769    0.3504    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5030    1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.0961    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4322   -1.5784   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.7498    0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8244    0.1120   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7032    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.8404    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222   -0.8983   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395   -0.8505   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.3698   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7749   -0.0956    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461    1.0275    1.8582 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  2  0
 21  6  1  0
 19 13  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 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      10.929   6.775   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.006   3.936   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.460   6.761   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.314   3.685   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.699   5.311   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       1.683   4.391   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.316   6.511   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      -2.350   3.812   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      10.236   5.399   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   10                                                       
CONECT    5    3   11                                                       
CONECT    6    8   12                                                       
CONECT    7    9   13                                                       
CONECT    8    2    6   17                                                  
CONECT    9    3    7   19                                                  
CONECT   10    4   12   14                                                  
CONECT   11    5   13   15                                                  
CONECT   12    6   10   20                                                  
CONECT   13    7   11   21                                                  
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   12   15                                                       
CONECT   21   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0029584
HETATM    1  C1  UNL     1      -5.838  -0.653   0.048  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.004  -0.160   1.081  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.645  -0.111   0.877  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.837   0.375   1.901  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.463   0.459   1.779  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.881   0.042   0.599  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.639  -0.449  -0.447  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.018  -0.516  -0.285  1.00  0.00           C  
HETATM    9  O2  UNL     1      -1.124  -0.854  -1.583  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.171  -0.812  -1.788  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.620  -1.217  -2.910  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.994  -0.337  -0.797  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.361  -0.173  -0.716  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.384  -0.436  -1.618  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.680  -0.163  -1.245  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.933   0.363   0.009  1.00  0.00           C  
HETATM   17  O4  UNL     1       6.248   0.630   0.360  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.907   0.615   0.885  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.577   0.350   0.541  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.448   0.503   1.193  1.00  0.00           O  
HETATM   21  C16 UNL     1       0.485   0.096   0.406  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.432  -1.578  -0.370  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.895  -0.750   0.406  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.824   0.112  -0.758  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.289   0.703   2.828  1.00  0.00           H  
HETATM   26  H5  UNL     1      -0.835   0.840   2.584  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.622  -0.898  -1.096  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.140  -0.850  -2.596  1.00  0.00           H  
HETATM   29  H8  UNL     1       5.479  -0.370  -1.955  1.00  0.00           H  
HETATM   30  H9  UNL     1       6.775  -0.096   0.806  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.146   1.027   1.858  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   11   12
CONECT   12   13   21   21
CONECT   13   14   14   19
CONECT   14   15   28
CONECT   15   16   16   29
CONECT   16   17   18
CONECT   17   30
CONECT   18   19   19   31
CONECT   19   20
CONECT   20   21
END

HMDB0029584
     RDKit          3D
3-O-Methylcoumestrol
 31 34  0  0  0  0  0  0  0  0999 V2000
   -5.8384   -0.6530    0.0484 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0041   -0.1599    1.0813 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -0.1115    0.8769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8373    0.3753    1.9006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4630    0.4586    1.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8812    0.0422    0.5990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6386   -0.4487   -0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0184   -0.5161   -0.2850 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1243   -0.8538   -1.5829 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1705   -0.8117   -1.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6203   -1.2172   -2.9097 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9938   -0.3366   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3609   -0.1732   -0.7163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3842   -0.4357   -1.6176 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6796   -0.1626   -1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9335    0.3635    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2483    0.6298    0.3602 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9071    0.6154    0.8851 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5769    0.3504    0.5411 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4482    0.5030    1.1932 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4853    0.0961    0.4064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4322   -1.5784   -0.3697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8955   -0.7498    0.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8244    0.1120   -0.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2886    0.7032    2.8284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8348    0.8404    2.5837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6222   -0.8983   -1.0959 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1395   -0.8505   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4787   -0.3698   -1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7749   -0.0956    0.8063 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1461    1.0275    1.8582 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  2  0
 10 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 12  2  0
 21  6  1  0
 19 13  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
 14 28  1  0
 15 29  1  0
 17 30  1  0
 18 31  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₀O₅

Average Molecular Weight

282.2476

Monoisotopic Molecular Weight

282.05282343

IUPAC Name

14-hydroxy-5-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

14-hydroxy-5-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

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2

InChI Identifier

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

InChI Key

YQBVKPREVBFWSA-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0029584)

Cellular substructure

Membrane (HMDB: HMDB0029584)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029584)

Source

Endogenous

Endogenous (HMDB: HMDB0029584)

Plant

Plant (HMDB: HMDB0029584)
Fabaceae (HMDB: HMDB0029584)

Exogenous

Food

Food (HMDB: HMDB0029584)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	331 - 332 °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	0.12 g/L	ALOGPS
logP	2.85	ALOGPS
logP	2.54	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	9.11	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	28.56 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]+	165.239	31661259
DarkChem	[M-H]-	167.184	31661259
DeepCCS	[M+H]+	171.801	30932474
DeepCCS	[M-H]-	169.443	30932474
DeepCCS	[M-2H]-	203.0	30932474
DeepCCS	[M+Na]+	178.227	30932474
AllCCS	[M+H]+	163.6	32859911
AllCCS	[M+H-H2O]+	159.8	32859911
AllCCS	[M+NH4]+	167.2	32859911
AllCCS	[M+Na]+	168.2	32859911
AllCCS	[M-H]-	166.2	32859911
AllCCS	[M+Na-2H]-	165.1	32859911
AllCCS	[M+HCOO]-	164.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	3948.8	Standard polar	33892256
3-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	2830.6	Standard non polar	33892256
3-O-Methylcoumestrol	COC1=CC2=C(C=C1)C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2	2946.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-O-Methylcoumestrol,1TMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C)=CC=C21	3028.1	Semi standard non polar	33892256
3-O-Methylcoumestrol,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC(=O)C1=C2OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C21	3228.6	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 - 3-O-Methylcoumestrol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-0490000000-cba5f4c071c5393c28c4	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-O-Methylcoumestrol GC-MS (1 TMS) - 70eV, Positive	splash10-0fki-4197000000-9e51f119108be8fef4d1	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-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 - 3-O-Methylcoumestrol 10V, Positive-QTOF	splash10-001i-0090000000-b09bbfda6b29f9d4e3d7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 20V, Positive-QTOF	splash10-001i-0090000000-dd96a1cd276243f97a62	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 40V, Positive-QTOF	splash10-0fvi-0090000000-3bbaf93ea49e7d320735	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 10V, Negative-QTOF	splash10-001i-0090000000-a72546420e5b02b2530d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 20V, Negative-QTOF	splash10-001i-0090000000-4cefe4cd801405abb52e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 40V, Negative-QTOF	splash10-014i-1090000000-7842c0d1bd388f6220ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 10V, Negative-QTOF	splash10-001i-0090000000-60166d79143e3c19fb0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 20V, Negative-QTOF	splash10-001i-0090000000-de1a1ea5c909df16fe07	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 40V, Negative-QTOF	splash10-014r-0090000000-def46988453eafad9b84	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 10V, Positive-QTOF	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 20V, Positive-QTOF	splash10-001i-0090000000-03c912f44b4d54fe7f1b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-O-Methylcoumestrol 40V, Positive-QTOF	splash10-057r-0090000000-b2a8787b30190a4c0431	2021-09-22	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

FDB000743

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131750884

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.. .

Showing metabocard for 3-O-Methylcoumestrol (HMDB0029584)

MOL for HMDB0029584 (3-O-Methylcoumestrol)

3D MOL for HMDB0029584 (3-O-Methylcoumestrol)

3D SDF for HMDB0029584 (3-O-Methylcoumestrol)

3D-SDF for HMDB0029584 (3-O-Methylcoumestrol)

PDB for HMDB0029584 (3-O-Methylcoumestrol)

3D PDB for HMDB0029584 (3-O-Methylcoumestrol)

SMILES for HMDB0029584 (3-O-Methylcoumestrol)

INCHI for HMDB0029584 (3-O-Methylcoumestrol)

Structure for HMDB0029584 (3-O-Methylcoumestrol)

3D Structure for HMDB0029584 (3-O-Methylcoumestrol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra