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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:46:36 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034001

Secondary Accession Numbers

HMDB34001

Metabolite Identification

Common Name

3-Hydroxy-4,9-dimethoxypterocarpan

Description

3-Hydroxy-4,9-dimethoxypterocarpan belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 3-hydroxy-4,9-dimethoxypterocarpan is considered to be a flavonoid. 3-Hydroxy-4,9-dimethoxypterocarpan has been detected, but not quantified in, several different foods, such as green tea, red tea, teas (Camellia sinensis), herbal tea, and green vegetables. This could make 3-hydroxy-4,9-dimethoxypterocarpan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Hydroxy-4,9-dimethoxypterocarpan.

Structure

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

HMDB0034001
     RDKit          3D
3-Hydroxy-4,9-dimethoxypterocarpan
 38 41  0  0  0  0  0  0  0  0999 V2000
    6.3121    1.1973    0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7370    0.1898   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931   -0.1111   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9681   -1.1404   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.4728   -1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -0.7686   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.2754    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531    0.5690    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    0.8099    0.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.5850   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5417    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1291    1.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    0.9980    2.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    0.2628    1.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    0.1032    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6653   -0.3412    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412   -1.0922   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -0.3760   -1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1905   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.7964   -1.4278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397   -1.1730   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -0.8640   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783    2.2260   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0139    1.1747    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284    1.0297    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -1.7092   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -2.2865   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8016    1.3751    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    1.2543   -0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    1.6990    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    1.4508    2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640    0.5344    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890   -0.2451   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -0.9547   -2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.6430   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5630   -2.2974   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277   -0.7457   -2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -1.4835    0.4310 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  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END


  Mrv0541 05061307292D          

 22 25  0  0  0  0            999 V2000
    7.2186    1.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1396   -0.5135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7521    1.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188    0.8259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.3869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9763    2.3397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0972    2.4741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1579    0.3177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7913    2.0281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3248    1.2719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2526    1.6971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    1.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6053    1.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3640    2.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0762    1.7443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8816    0.9603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0579    0.9131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2184    1.5557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5246    2.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6869    0.1762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343    0.2705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5923    2.3879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  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  8  1  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 10  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16 11  2  0  0  0  0
 17 13  2  0  0  0  0
 17 16  1  0  0  0  0
 18 13  1  0  0  0  0
 19  1  1  0  0  0  0
 19  9  1  0  0  0  0
 20  2  1  0  0  0  0
 20 17  1  0  0  0  0
 21  8  1  0  0  0  0
 21 16  1  0  0  0  0
 22 14  1  0  0  0  0
 22 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034001

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3OC)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-16-11(15(12)22-14(10)7-9)5-6-13(18)17(16)20-2/h3-7,12,15,18H,8H2,1-2H3

> <INCHI_KEY>
IPDALSAPRYQWGQ-UHFFFAOYSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.167074073777535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
2.3515521306666667

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.933505551443893

> <JCHEM_PKA_STRONGEST_BASIC>
-4.305019631408488

> <JCHEM_POLAR_SURFACE_AREA>
57.150000000000006

> <JCHEM_REFRACTIVITY>
79.52430000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034001
     RDKit          3D
3-Hydroxy-4,9-dimethoxypterocarpan
 38 41  0  0  0  0  0  0  0  0999 V2000
    6.3121    1.1973    0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7370    0.1898   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931   -0.1111   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9681   -1.1404   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.4728   -1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -0.7686   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.2754    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531    0.5690    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    0.8099    0.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.5850   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5417    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1291    1.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    0.9980    2.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    0.2628    1.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    0.1032    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6653   -0.3412    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412   -1.0922   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -0.3760   -1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1905   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.7964   -1.4278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397   -1.1730   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -0.8640   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783    2.2260   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0139    1.1747    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284    1.0297    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -1.7092   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -2.2865   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8016    1.3751    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    1.2543   -0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    1.6990    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    1.4508    2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640    0.5344    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890   -0.2451   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -0.9547   -2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.6430   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5630   -2.2974   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277   -0.7457   -2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -1.4835    0.4310 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  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  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      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.127  -0.959   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.282   0.329   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   13                                                       
CONECT    7    9   14                                                       
CONECT    8   12   21                                                       
CONECT    9    3    7   19                                                  
CONECT   10    4   12   14                                                  
CONECT   11    5   15   16                                                  
CONECT   12    8   10   15                                                  
CONECT   13    6   17   18                                                  
CONECT   14    7   10   22                                                  
CONECT   15   11   12   22                                                  
CONECT   16   11   17   21                                                  
CONECT   17   13   16   20                                                  
CONECT   18   13                                                            
CONECT   19    1    9                                                       
CONECT   20    2   17                                                       
CONECT   21    8   16                                                       
CONECT   22   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   50    0
END

COMPND    HMDB0034001
HETATM    1  C1  UNL     1       6.312   1.197   0.378  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.737   0.190  -0.393  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.393  -0.111  -0.440  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.968  -1.140  -1.253  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.641  -1.473  -1.329  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.702  -0.769  -0.580  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.099   0.275   0.250  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.453   0.569   0.289  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.956   0.810   0.885  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.083   0.585  -0.036  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.435   0.542   0.506  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.891   1.129   1.652  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.207   0.998   2.039  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.098   0.263   1.268  1.00  0.00           C  
HETATM   15  O3  UNL     1      -5.433   0.103   1.617  1.00  0.00           O  
HETATM   16  C13 UNL     1      -3.665  -0.341   0.106  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.541  -1.092  -0.698  1.00  0.00           O  
HETATM   18  C14 UNL     1      -5.227  -0.376  -1.711  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.346  -0.190  -0.251  1.00  0.00           C  
HETATM   20  O5  UNL     1      -1.888  -0.796  -1.428  1.00  0.00           O  
HETATM   21  C16 UNL     1      -0.540  -1.173  -1.641  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.253  -0.864  -0.430  1.00  0.00           C  
HETATM   23  H1  UNL     1       6.178   2.226  -0.068  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.014   1.175   1.441  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.428   1.030   0.382  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.689  -1.709  -1.852  1.00  0.00           H  
HETATM   27  H5  UNL     1       2.278  -2.287  -1.967  1.00  0.00           H  
HETATM   28  H6  UNL     1       3.802   1.375   0.923  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.041   1.254  -0.903  1.00  0.00           H  
HETATM   30  H8  UNL     1      -1.160   1.699   2.232  1.00  0.00           H  
HETATM   31  H9  UNL     1      -3.570   1.451   2.928  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.764   0.534   2.457  1.00  0.00           H  
HETATM   33  H11 UNL     1      -6.289  -0.245  -1.376  1.00  0.00           H  
HETATM   34  H12 UNL     1      -5.252  -0.955  -2.669  1.00  0.00           H  
HETATM   35  H13 UNL     1      -4.812   0.643  -1.867  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.563  -2.297  -1.751  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.128  -0.746  -2.562  1.00  0.00           H  
HETATM   38  H16 UNL     1      -0.051  -1.484   0.431  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   22
CONECT    7    8    8    9
CONECT    8   28
CONECT    9   10
CONECT   10   11   22   29
CONECT   11   12   12   19
CONECT   12   13   30
CONECT   13   14   14   31
CONECT   14   15   16
CONECT   15   32
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   33   34   35
CONECT   19   20
CONECT   20   21
CONECT   21   22   36   37
CONECT   22   38
END

HMDB0034001
     RDKit          3D
3-Hydroxy-4,9-dimethoxypterocarpan
 38 41  0  0  0  0  0  0  0  0999 V2000
    6.3121    1.1973    0.3777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7370    0.1898   -0.3931 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3931   -0.1111   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9681   -1.1404   -1.2527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6411   -1.4728   -1.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7022   -0.7686   -0.5798 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0993    0.2754    0.2499 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531    0.5690    0.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9565    0.8099    0.8852 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0835    0.5850   -0.0356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4348    0.5417    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8910    1.1291    1.6521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2073    0.9980    2.0391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0983    0.2628    1.2676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4331    0.1032    1.6174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6653   -0.3412    0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5412   -1.0922   -0.6980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2271   -0.3760   -1.7106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461   -0.1905   -0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8884   -0.7964   -1.4278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5397   -1.1730   -1.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2531   -0.8640   -0.4296 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1783    2.2260   -0.0680 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0139    1.1747    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4284    1.0297    0.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6889   -1.7092   -1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2781   -2.2865   -1.9672 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8016    1.3751    0.9234 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407    1.2543   -0.9025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1602    1.6990    2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5704    1.4508    2.9275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7640    0.5344    2.4568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2890   -0.2451   -1.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2524   -0.9547   -2.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8116    0.6430   -1.8671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5630   -2.2974   -1.7513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1277   -0.7457   -2.5618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0514   -1.4835    0.4310 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  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
  8  3  1  0
 22 10  1  0
 22  6  1  0
 19 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  8 28  1  0
 10 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 18 33  1  0
 18 34  1  0
 18 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methoxymedicarpin	HMDB

Chemical Formula

C₁₇H₁₆O₅

Average Molecular Weight

300.3059

Monoisotopic Molecular Weight

300.099773622

IUPAC Name

6,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

Traditional Name

6,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-ol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3OC)C1O2

InChI Identifier

InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-16-11(15(12)22-14(10)7-9)5-6-13(18)17(16)20-2/h3-7,12,15,18H,8H2,1-2H3

InChI Key

IPDALSAPRYQWGQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Chromane
1-benzopyran
Benzopyran
Coumaran
Benzofuran
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070075 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0034001)
Cell membrane (HMDB: HMDB0034001)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034001)

Source

Exogenous

Exogenous (HMDB: HMDB0034001)

Food

Food (HMDB: HMDB0034001)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0034001)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034001)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	158 - 160 °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	0.088 g/L	ALOGPS
logP	2.84	ALOGPS
logP	2.35	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	57.15 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	79.52 m³·mol⁻¹	ChemAxon
Polarizability	31.17 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]+	171.322	31661259
DarkChem	[M-H]-	172.181	31661259
DeepCCS	[M+H]+	171.775	30932474
DeepCCS	[M-H]-	169.417	30932474
DeepCCS	[M-2H]-	202.88	30932474
DeepCCS	[M+Na]+	178.107	30932474
AllCCS	[M+H]+	170.5	32859911
AllCCS	[M+H-H2O]+	166.9	32859911
AllCCS	[M+NH4]+	173.8	32859911
AllCCS	[M+Na]+	174.8	32859911
AllCCS	[M-H]-	175.1	32859911
AllCCS	[M+Na-2H]-	174.5	32859911
AllCCS	[M+HCOO]-	174.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4,9-dimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3OC)C1O2	3784.2	Standard polar	33892256
3-Hydroxy-4,9-dimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3OC)C1O2	2507.5	Standard non polar	33892256
3-Hydroxy-4,9-dimethoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3OC)C1O2	2629.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4,9-dimethoxypterocarpan,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(OC)=C3OCC21	2672.4	Semi standard non polar	33892256
3-Hydroxy-4,9-dimethoxypterocarpan,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3OCC21	2914.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dr-0790000000-27346d1e85e0819b550f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan GC-MS (1 TMS) - 70eV, Positive	splash10-0ab9-1239000000-4a90100aff37975e9622	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 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-4,9-dimethoxypterocarpan 10V, Positive-QTOF	splash10-0udi-0019000000-79332597f0703d155329	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 20V, Positive-QTOF	splash10-0udi-0149000000-9a4c08d7133ca1bc169e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 40V, Positive-QTOF	splash10-0pb9-6980000000-56f56d361d6f297aa915	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 10V, Negative-QTOF	splash10-0002-0090000000-3324977917d7d0400788	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 20V, Negative-QTOF	splash10-0002-0090000000-30b952591555af6ce198	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 40V, Negative-QTOF	splash10-0zfr-1290000000-27119fc14d8c83a5ff41	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 10V, Negative-QTOF	splash10-0002-0090000000-c8e04b941de97dd002f4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 20V, Negative-QTOF	splash10-0002-0090000000-680de81a2c4e5602450a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 40V, Negative-QTOF	splash10-0ufr-0290000000-ada9df73089431de4510	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 10V, Positive-QTOF	splash10-0udi-0009000000-7fd5921050e52686aed7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 20V, Positive-QTOF	splash10-0udi-0309000000-511d760658fa9ec6c966	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4,9-dimethoxypterocarpan 40V, Positive-QTOF	splash10-03mi-0940000000-25d2a406045e48ee6a01	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

FDB012235

KNApSAcK ID

C00030922

Chemspider ID

4446401

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283280

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-4,9-dimethoxypterocarpan → 6-({6,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Showing metabocard for 3-Hydroxy-4,9-dimethoxypterocarpan (HMDB0034001)

MOL for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

3D MOL for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

3D SDF for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

3D-SDF for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

PDB for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

3D PDB for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

SMILES for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

INCHI for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

Structure for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

3D Structure for HMDB0034001 (3-Hydroxy-4,9-dimethoxypterocarpan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions