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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:47:13 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034012

Secondary Accession Numbers

HMDB34012

Metabolite Identification

Common Name

3,4-Dihydroxy-9-methoxypterocarpan

Description

3,4-Dihydroxy-9-methoxypterocarpan 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, 3,4-dihydroxy-9-methoxypterocarpan is considered to be a flavonoid. 3,4-Dihydroxy-9-methoxypterocarpan has been detected, but not quantified in, herbs and spices and pulses. This could make 3,4-dihydroxy-9-methoxypterocarpan a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on 3,4-Dihydroxy-9-methoxypterocarpan.

Structure

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

HMDB0034012
     RDKit          3D
3,4-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.2137   -0.1239   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -1.0193   -0.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.5379   -0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    0.8043   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    1.3057   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    0.4909   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.8720   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -1.3710   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836   -1.5300   -0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6749    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919   -0.7937    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8850   -0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -1.8547   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.7244   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760   -0.7419   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019    0.3949    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9557    1.5093    0.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347    0.3348    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    1.4088    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903    1.7291    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345    0.6624   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215    0.4881    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1717   -0.6816   -0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    0.6042   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4299    1.5254   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758    2.3714   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.4309   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -0.6380    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -2.7459   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -2.7214   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    0.0267   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575    2.3039    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675    2.0224    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    2.6564   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    0.7078   -1.4055 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
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 10  1  0
 21  6  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061307302D          

 21 24  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
    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
    1.0579    0.9131    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
   -0.2184    1.5557    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
    6.5246    2.4062    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
  3  2  2  0  0  0  0
  5  4  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
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  1  0  0  0  0
 13  9  2  0  0  0  0
 14 12  2  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19  8  1  0  0  0  0
 20  7  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034012

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3

> <INCHI_KEY>
YRFDJOAWSXSLMG-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.176521781600364

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.67

> <JCHEM_LOGP>
2.2056580746666663

> <ALOGPS_LOGS>
-3.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.96255721045079

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.46441706267162

> <JCHEM_PKA_STRONGEST_BASIC>
-4.412805736540249

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
75.04200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034012
     RDKit          3D
3,4-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.2137   -0.1239   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -1.0193   -0.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.5379   -0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    0.8043   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    1.3057   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    0.4909   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.8720   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -1.3710   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836   -1.5300   -0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6749    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919   -0.7937    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8850   -0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -1.8547   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.7244   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760   -0.7419   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019    0.3949    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9557    1.5093    0.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347    0.3348    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    1.4088    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903    1.7291    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345    0.6624   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215    0.4881    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1717   -0.6816   -0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    0.6042   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4299    1.5254   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758    2.3714   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.4309   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -0.6380    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -2.7459   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -2.7214   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    0.0267   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575    2.3039    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675    2.0224    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    2.6564   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    0.7078   -1.4055 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
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 10  1  0
 21  6  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 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      13.475   3.659   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.975   1.704   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  O   UNK     0      -0.408   2.904   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.282   0.329   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       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    8                                                       
CONECT    3    2    9                                                       
CONECT    4    5   10                                                       
CONECT    5    4   12                                                       
CONECT    6    8   13                                                       
CONECT    7   11   20                                                       
CONECT    8    2    6   19                                                  
CONECT    9    3   11   13                                                  
CONECT   10    4   15   16                                                  
CONECT   11    7    9   15                                                  
CONECT   12    5   14   17                                                  
CONECT   13    6    9   21                                                  
CONECT   14   12   16   18                                                  
CONECT   15   10   11   21                                                  
CONECT   16   10   14   20                                                  
CONECT   17   12                                                            
CONECT   18   14                                                            
CONECT   19    1    8                                                       
CONECT   20    7   16                                                       
CONECT   21   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0034012
HETATM    1  C1  UNL     1       6.214  -0.124  -0.429  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.131  -1.019  -0.470  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.848  -0.538  -0.434  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.612   0.804  -0.360  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.329   1.306  -0.323  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.217   0.491  -0.359  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.437  -0.872  -0.435  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.738  -1.371  -0.471  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.184  -1.530  -0.460  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.646  -0.675   0.283  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.092  -0.794   0.030  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.713  -1.885  -0.491  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.079  -1.855  -0.674  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.813  -0.724  -0.330  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.176  -0.742  -0.532  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.202   0.395   0.201  1.00  0.00           C  
HETATM   17  O4  UNL     1      -4.956   1.509   0.535  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.835   0.335   0.372  1.00  0.00           C  
HETATM   19  O5  UNL     1      -2.137   1.409   0.897  1.00  0.00           O  
HETATM   20  C15 UNL     1      -0.790   1.729   0.514  1.00  0.00           C  
HETATM   21  C16 UNL     1      -0.235   0.662  -0.346  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.121   0.488   0.498  1.00  0.00           H  
HETATM   23  H2  UNL     1       7.172  -0.682  -0.429  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.167   0.604  -1.278  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.430   1.525  -0.327  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.176   2.371  -0.264  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.933  -2.431  -0.531  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.428  -0.638   1.350  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.119  -2.746  -0.748  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.612  -2.721  -1.094  1.00  0.00           H  
HETATM   31  H10 UNL     1      -6.769   0.027  -0.311  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.457   2.304   0.921  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.167   2.022   1.361  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.903   2.656  -0.121  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.580   0.708  -1.405  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   21
CONECT    7    8    8    9
CONECT    8   27
CONECT    9   10
CONECT   10   11   21   28
CONECT   11   12   12   18
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31
CONECT   16   17   18   18
CONECT   17   32
CONECT   18   19
CONECT   19   20
CONECT   20   21   33   34
CONECT   21   35
END

HMDB0034012
     RDKit          3D
3,4-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    6.2137   -0.1239   -0.4293 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1307   -1.0193   -0.4698 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8485   -0.5379   -0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6117    0.8043   -0.3597 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3290    1.3057   -0.3232 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2169    0.4909   -0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4368   -0.8720   -0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7375   -1.3710   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1836   -1.5300   -0.4602 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6460   -0.6749    0.2829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0919   -0.7937    0.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7127   -1.8850   -0.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0787   -1.8547   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8132   -0.7244   -0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1760   -0.7419   -0.5317 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2019    0.3949    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9557    1.5093    0.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8347    0.3348    0.3719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    1.4088    0.8974 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7903    1.7291    0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345    0.6624   -0.3463 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215    0.4881    0.4978 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1717   -0.6816   -0.4289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1673    0.6042   -1.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4299    1.5254   -0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1758    2.3714   -0.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -2.4309   -0.5309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283   -0.6380    1.3499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1188   -2.7459   -0.7478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6118   -2.7214   -1.0936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7688    0.0267   -0.3114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4575    2.3039    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1675    2.0224    1.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9025    2.6564   -0.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5797    0.7078   -1.4055 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
 16 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 10  1  0
 21  6  1  0
 18 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 20 33  1  0
 20 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Hydroxymedicarpin	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol

Traditional Name

14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-5,6-diol

CAS Registry Number

53950-54-2

SMILES

COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

InChI Identifier

InChI=1S/C16H14O5/c1-19-8-2-3-9-11-7-20-16-10(4-5-12(17)14(16)18)15(11)21-13(9)6-8/h2-6,11,15,17-18H,7H2,1H3

InChI Key

YRFDJOAWSXSLMG-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

Isoflavanol
Pterocarpan
Isoflavan
Chromane
Benzopyran
1-benzopyran
Benzofuran
Coumaran
Anisole
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Pterocarpans (LMPK12070074 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.25 g/L	ALOGPS
logP	2.67	ALOGPS
logP	2.21	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	68.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	75.04 m³·mol⁻¹	ChemAxon
Polarizability	29.18 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]+	168.417	31661259
DarkChem	[M-H]-	167.874	31661259
DeepCCS	[M+H]+	169.768	30932474
DeepCCS	[M-H]-	167.41	30932474
DeepCCS	[M-2H]-	200.889	30932474
DeepCCS	[M+Na]+	176.116	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.3	32859911
AllCCS	[M+Na]+	171.3	32859911
AllCCS	[M-H]-	170.3	32859911
AllCCS	[M+Na-2H]-	169.6	32859911
AllCCS	[M+HCOO]-	168.9	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.	6.32 minutes	32390414
Predicted by Siyang on May 30, 2022	12.2518 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1808.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	301.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	178.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	149.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	596.4 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	562.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1060.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	430.0 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	1202.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	346.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	379.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	403.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	240.6 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	74.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	3697.5	Standard polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	2499.2	Standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	2688.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4-Dihydroxy-9-methoxypterocarpan,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O)=C3OCC21	2724.6	Semi standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan,1TMS,isomer #2	COC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C)=C3OCC21	2670.4	Semi standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan,2TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3OCC21	2708.5	Semi standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3OCC21	2991.4	Semi standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan,1TBDMS,isomer #2	COC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	2933.7	Semi standard non polar	33892256
3,4-Dihydroxy-9-methoxypterocarpan,2TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3180.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	splash10-05fs-0790000000-ba71b409fadb1d3269f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan GC-MS (2 TMS) - 70eV, Positive	splash10-06di-4469600000-0a5f3efa5d73525aa0fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 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 - 3,4-Dihydroxy-9-methoxypterocarpan 10V, Positive-QTOF	splash10-002r-0690000000-f70c15b4e9ca3a937f43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 20V, Positive-QTOF	splash10-002r-0790000000-f6b1882162bfa73a4489	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 40V, Positive-QTOF	splash10-016r-9600000000-5ee58d5c75f2ae3e9ca2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 10V, Negative-QTOF	splash10-000i-0090000000-71f54f138334c0235fcd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 20V, Negative-QTOF	splash10-000i-0090000000-f434556d516953340de0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 40V, Negative-QTOF	splash10-0a4r-2960000000-ba5b6733b84f8f0ef91f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 20V, Positive-QTOF	splash10-01p9-0980000000-d42a32196bc6ddaa5409	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 40V, Positive-QTOF	splash10-03di-0910000000-8b3c5e67ae4b1bfc6da0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 20V, Negative-QTOF	splash10-000i-0090000000-cf20ef0a413d213a98c9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4-Dihydroxy-9-methoxypterocarpan 40V, Negative-QTOF	splash10-014i-1390000000-19407ff3efa9a6baaf77	2021-09-23	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

FDB012248

KNApSAcK ID

Not Available

Chemspider ID

9711318

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11536537

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

3,4-Dihydroxy-9-methoxypterocarpan → 3,4,5-trihydroxy-6-({5-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-6-yl}oxy)oxane-2-carboxylic acid	details
3,4-Dihydroxy-9-methoxypterocarpan → 3,4,5-trihydroxy-6-({6-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaen-5-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 3,4-Dihydroxy-9-methoxypterocarpan (HMDB0034012)

MOL for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

3D MOL for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

3D SDF for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

3D-SDF for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

PDB for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

3D PDB for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

SMILES for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

INCHI for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

Structure for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

3D Structure for HMDB0034012 (3,4-Dihydroxy-9-methoxypterocarpan)

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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