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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:37:38 UTC

Update Date

2022-03-07 02:52:36 UTC

HMDB ID

HMDB0030561

Secondary Accession Numbers

HMDB30561

Metabolite Identification

Common Name

3-Hydroxy-8,9-dimethoxycoumestan

Description

3-Hydroxy-8,9-dimethoxycoumestan 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, 3-hydroxy-8,9-dimethoxycoumestan is considered to be a flavonoid. 3-Hydroxy-8,9-dimethoxycoumestan has been detected, but not quantified in, alfalfas (Medicago sativa) and pulses. This could make 3-hydroxy-8,9-dimethoxycoumestan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxy-8,9-dimethoxycoumestan.

Structure

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

HMDB0030561
     RDKit          3D
3-Hydroxy-8,9-dimethoxycoumestan
 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.3983    2.8598   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.4885   -0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1849    0.8370   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    1.4905   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572    0.8964   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    1.2906   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.3252   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    0.2604   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696    1.3771   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    1.2770   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722    0.1145   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8568    0.0860   -0.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028   -0.9825    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -0.9390    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -1.9888    0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -1.9624    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.9703    0.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -0.7961    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -0.4468    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -1.1273    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -0.4903    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2950   -1.1736    0.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530   -2.5300    0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    3.4074    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3936    3.3082   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    2.9602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    2.5405   -0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9361    2.2871   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    2.1592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.7259   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -1.8986    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053   -2.1693    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -2.6692    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3193   -2.9970    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -3.0986    0.2362 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 19  5  2  0
 18  7  2  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 20 32  1  0
 23 33  1  0
 23 34  1  0
 23 35  1  0
M  END


  Mrv0541 05061305212D          

 23 26  0  0  0  0            999 V2000
   -1.9140    3.3120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -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
    3.4655    2.0613    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
    0.2466    3.6222    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
    3.0128    2.7510    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
    3.3838    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
   -0.4867    3.2441    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
    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
   -1.1807    3.6901    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  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18  8  1  0  0  0  0
 19 17  2  0  0  0  0
 20  1  1  0  0  0  0
 20 13  1  0  0  0  0
 21  2  1  0  0  0  0
 21 14  1  0  0  0  0
 22 12  1  0  0  0  0
 22 16  1  0  0  0  0
 23 11  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030561

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3

> <INCHI_KEY>
PKLPURDVDNBFCI-UHFFFAOYSA-N

> <FORMULA>
C17H12O6

> <MOLECULAR_WEIGHT>
312.2736

> <EXACT_MASS>
312.063388116

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.595376212289068

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-13,14-dimethoxy-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>
2.50

> <JCHEM_LOGP>
2.385544112666666

> <ALOGPS_LOGS>
-3.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.117751669730867

> <JCHEM_PKA_STRONGEST_BASIC>
-4.109703129647038

> <JCHEM_POLAR_SURFACE_AREA>
78.13000000000001

> <JCHEM_REFRACTIVITY>
80.56500000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-13,14-dimethoxy-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

$$$$

HMDB0030561
     RDKit          3D
3-Hydroxy-8,9-dimethoxycoumestan
 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.3983    2.8598   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.4885   -0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1849    0.8370   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    1.4905   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572    0.8964   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    1.2906   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.3252   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    0.2604   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696    1.3771   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    1.2770   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722    0.1145   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8568    0.0860   -0.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028   -0.9825    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -0.9390    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -1.9888    0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -1.9624    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.9703    0.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -0.7961    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -0.4468    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -1.1273    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -0.4903    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2950   -1.1736    0.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530   -2.5300    0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    3.4074    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3936    3.3082   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    2.9602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    2.5405   -0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9361    2.2871   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    2.1592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.7259   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -1.8986    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053   -2.1693    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -2.6692    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3193   -2.9970    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -3.0986    0.2362 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 19  5  2  0
 18  7  2  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 20 32  1  0
 23 33  1  0
 23 34  1  0
 23 35  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      -3.573   6.182   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.646   4.644   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       6.469   3.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.854   6.599   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.460   6.761   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       5.624   5.135   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       6.316   6.511   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      -0.909   6.056   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.982   4.518   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.241   6.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.087   5.047   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.934   7.710   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      10.236   5.399   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      -2.204   6.888   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.350   3.812   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.123   3.846   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.472   7.798   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2   21                                                            
CONECT    3    4    8                                                       
CONECT    4    3    9                                                       
CONECT    5    8   11                                                       
CONECT    6   10   13                                                       
CONECT    7   12   14                                                       
CONECT    8    3    5   18                                                  
CONECT    9    4   11   16                                                  
CONECT   10    6   12   15                                                  
CONECT   11    5    9   23                                                  
CONECT   12    7   10   22                                                  
CONECT   13    6   14   20                                                  
CONECT   14    7   13   21                                                  
CONECT   15   10   16   17                                                  
CONECT   16    9   15   22                                                  
CONECT   17   15   19   23                                                  
CONECT   18    8                                                            
CONECT   19   17                                                            
CONECT   20    1   13                                                       
CONECT   21    2   14                                                       
CONECT   22   12   16                                                       
CONECT   23   11   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0030561
HETATM    1  C1  UNL     1      -4.398   2.860  -0.649  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.410   1.489  -0.274  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.185   0.837  -0.139  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.991   1.490  -0.360  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.757   0.896  -0.241  1.00  0.00           C  
HETATM    6  O2  UNL     1       0.500   1.291  -0.393  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.324   0.325  -0.158  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.702   0.260  -0.189  1.00  0.00           C  
HETATM    9  C7  UNL     1       3.470   1.377  -0.521  1.00  0.00           C  
HETATM   10  C8  UNL     1       4.828   1.277  -0.542  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.472   0.115  -0.247  1.00  0.00           C  
HETATM   12  O3  UNL     1       6.857   0.086  -0.288  1.00  0.00           O  
HETATM   13  C10 UNL     1       4.703  -0.982   0.080  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.314  -0.939   0.117  1.00  0.00           C  
HETATM   15  O4  UNL     1       2.598  -1.989   0.429  1.00  0.00           O  
HETATM   16  C12 UNL     1       1.273  -1.962   0.469  1.00  0.00           C  
HETATM   17  O5  UNL     1       0.585  -2.970   0.769  1.00  0.00           O  
HETATM   18  C13 UNL     1       0.600  -0.796   0.174  1.00  0.00           C  
HETATM   19  C14 UNL     1      -0.725  -0.447   0.125  1.00  0.00           C  
HETATM   20  C15 UNL     1      -1.905  -1.127   0.353  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.119  -0.490   0.221  1.00  0.00           C  
HETATM   22  O6  UNL     1      -4.295  -1.174   0.449  1.00  0.00           O  
HETATM   23  C17 UNL     1      -4.353  -2.530   0.822  1.00  0.00           C  
HETATM   24  H1  UNL     1      -3.738   3.407   0.074  1.00  0.00           H  
HETATM   25  H2  UNL     1      -5.394   3.308  -0.627  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.920   2.960  -1.653  1.00  0.00           H  
HETATM   27  H4  UNL     1      -2.038   2.541  -0.645  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.936   2.287  -0.751  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.394   2.159  -0.803  1.00  0.00           H  
HETATM   30  H7  UNL     1       7.419  -0.726  -0.086  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.194  -1.899   0.313  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.805  -2.169   0.634  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.239  -2.669   1.910  1.00  0.00           H  
HETATM   34  H11 UNL     1      -5.319  -2.997   0.536  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.577  -3.099   0.236  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   27
CONECT    5    6   19   19
CONECT    6    7
CONECT    7    8   18   18
CONECT    8    9    9   14
CONECT    9   10   28
CONECT   10   11   11   29
CONECT   11   12   13
CONECT   12   30
CONECT   13   14   14   31
CONECT   14   15
CONECT   15   16
CONECT   16   17   17   18
CONECT   18   19
CONECT   19   20
CONECT   20   21   21   32
CONECT   21   22
CONECT   22   23
CONECT   23   33   34   35
END

HMDB0030561
     RDKit          3D
3-Hydroxy-8,9-dimethoxycoumestan
 35 38  0  0  0  0  0  0  0  0999 V2000
   -4.3983    2.8598   -0.6494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4100    1.4885   -0.2742 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1849    0.8370   -0.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    1.4905   -0.3600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7572    0.8964   -0.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4996    1.2906   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3241    0.3252   -0.1582 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7017    0.2604   -0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4696    1.3771   -0.5214 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8278    1.2770   -0.5419 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4722    0.1145   -0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8568    0.0860   -0.2879 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7028   -0.9825    0.0801 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3141   -0.9390    0.1172 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5983   -1.9888    0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -1.9624    0.4688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846   -2.9703    0.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6004   -0.7961    0.1737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7248   -0.4468    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -1.1273    0.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1189   -0.4903    0.2212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2950   -1.1736    0.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3530   -2.5300    0.8221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7384    3.4074    0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3936    3.3082   -0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204    2.9602   -1.6526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    2.5405   -0.6453 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9361    2.2871   -0.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3943    2.1592   -0.8029 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4190   -0.7259   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1942   -1.8986    0.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8053   -2.1693    0.6338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2388   -2.6692    1.9098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3193   -2.9970    0.5358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5767   -3.0986    0.2362 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 21  3  1  0
 19  5  2  0
 18  7  2  0
 14  8  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 20 32  1  0
 23 33  1  0
 23 34  1  0
 23 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-Hydroxy-11,12-dimethoxycoumestan (obsol.)	HMDB
alpha-Ethyl-3-nitrocinnamic acid	HMDB

Chemical Formula

C₁₇H₁₂O₆

Average Molecular Weight

312.2736

Monoisotopic Molecular Weight

312.063388116

IUPAC Name

5-hydroxy-13,14-dimethoxy-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-hydroxy-13,14-dimethoxy-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

5252-40-4

SMILES

COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1

InChI Identifier

InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3

InChI Key

PKLPURDVDNBFCI-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 (LMPK12090028 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030561)
Cytoplasm (HMDB: HMDB0030561)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030561)

Source

Endogenous

Endogenous (HMDB: HMDB0030561)

Plant

Plant (HMDB: HMDB0030561)
Fabaceae (HMDB: HMDB0030561)

Exogenous

Food

Food (HMDB: HMDB0030561)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Pulse

Pulses (FooDB: FOOD00867)

Exogenous (HMDB: HMDB0030561)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	306 °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	2.5	ALOGPS
logP	2.39	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	7.12	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	78.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	80.56 m³·mol⁻¹	ChemAxon
Polarizability	31.6 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]+	170.867	31661259
DarkChem	[M-H]-	173.226	31661259
DeepCCS	[M+H]+	177.582	30932474
DeepCCS	[M-H]-	175.224	30932474
DeepCCS	[M-2H]-	209.122	30932474
DeepCCS	[M+Na]+	184.349	30932474
AllCCS	[M+H]+	170.6	32859911
AllCCS	[M+H-H2O]+	167.0	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	173.2	32859911
AllCCS	[M+Na-2H]-	172.2	32859911
AllCCS	[M+HCOO]-	171.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	6.2 minutes	32390414
Predicted by Siyang on May 30, 2022	14.0644 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2174.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	389.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	182.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	216.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	187.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	533.3 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	550.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	89.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1187.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.6 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	1467.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	397.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	352.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	343.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	359.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	30.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-8,9-dimethoxycoumestan	COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	4439.5	Standard polar	33892256
3-Hydroxy-8,9-dimethoxycoumestan	COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	3068.2	Standard non polar	33892256
3-Hydroxy-8,9-dimethoxycoumestan	COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1	3203.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-8,9-dimethoxycoumestan,1TMS,isomer #1	COC1=CC2=C(C=C1OC)C1=C(O2)C2=CC=C(O[Si](C)(C)C)C=C2OC1=O	3162.4	Semi standard non polar	33892256
3-Hydroxy-8,9-dimethoxycoumestan,1TBDMS,isomer #1	COC1=CC2=C(C=C1OC)C1=C(O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2OC1=O	3391.8	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-Hydroxy-8,9-dimethoxycoumestan GC-MS (Non-derivatized) - 70eV, Positive	splash10-015a-0091000000-02f30903e7d90b5f517c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan GC-MS (1 TMS) - 70eV, Positive	splash10-01dl-2319000000-5cb82e5c9d4f5a71a975	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 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-Hydroxy-8,9-dimethoxycoumestan 10V, Positive-QTOF	splash10-03di-0009000000-7847db498807d288a745	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Positive-QTOF	splash10-03di-0019000000-5e0a950b359893c61d69	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Positive-QTOF	splash10-0f8a-0090000000-5378a4a24ae0701e7d17	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Negative-QTOF	splash10-03di-0009000000-c2d8b516decd37e8c92e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Negative-QTOF	splash10-03di-0039000000-b23c8cb81c2945a75535	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Negative-QTOF	splash10-0a4j-1090000000-1b31caa06e41bc3396ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Positive-QTOF	splash10-03di-0009000000-fbd933023572de11abf0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Positive-QTOF	splash10-02t9-0092000000-93c3331a462a6af2b239	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 10V, Negative-QTOF	splash10-03di-0009000000-b504eaff11e6208b17b1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 20V, Negative-QTOF	splash10-03di-0069000000-42bdc5bce8039a801f0b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-8,9-dimethoxycoumestan 40V, Negative-QTOF	splash10-0f79-0090000000-345260f4d49707f7095e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB002445

KNApSAcK ID

C00009768

Chemspider ID

4678016

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5748556

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

3-Hydroxy-8,9-dimethoxycoumestan → 6-({13,14-dimethoxy-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 3-Hydroxy-8,9-dimethoxycoumestan (HMDB0030561)

MOL for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

3D MOL for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

3D SDF for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

3D-SDF for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

PDB for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

3D PDB for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

SMILES for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

INCHI for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

Structure for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

3D Structure for HMDB0030561 (3-Hydroxy-8,9-dimethoxycoumestan)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

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