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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:00:19 UTC

Update Date

2022-03-07 02:53:39 UTC

HMDB ID

HMDB0033291

Secondary Accession Numbers

HMDB33291

Metabolite Identification

Common Name

3,8-Dihydroxy-9-methoxypterocarpan

Description

3,8-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, 3,8-dihydroxy-9-methoxypterocarpan is considered to be a flavonoid. 3,8-Dihydroxy-9-methoxypterocarpan has been detected, but not quantified in, green vegetables. This could make 3,8-dihydroxy-9-methoxypterocarpan a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 3,8-Dihydroxy-9-methoxypterocarpan.

Structure

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

HMDB0033291
     RDKit          3D
3,8-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.2579   -0.1546   -1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686    0.1616   -0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6469    0.2167    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.0365   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.0107   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011    0.3204    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418    0.5696    1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.5266    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136    0.7773    2.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779    0.2936    1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750   -1.1250    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121   -1.4135    1.2048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956   -0.7560    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.0911   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133   -0.4534   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236   -0.7931   -1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850    0.5398   -1.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    0.8596   -1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    0.2412   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    0.6072   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -0.2009   -0.9113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    0.4504   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1249   -1.2316   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340    0.0814   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.2846   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203    0.8142    3.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    1.0060    3.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    1.0261    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.8165    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.3413    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6686   -1.8888    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9674   -0.3072   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8522    1.0333   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339    1.6628   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.6955   -0.3713 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
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 21  5  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END


  Mrv0541 02241211312D          

 21 24  0  0  0  0            999 V2000
   -2.6396    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796   -0.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946   -0.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471   -0.5771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7421    0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5671    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971   -0.7421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7222   -0.8246    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321   -2.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021   -1.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771   -1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2471    0.7421    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4946    0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    0.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2371    1.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9796    2.1446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6396    1.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3821    2.1446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 20  2  0  0  0  0
  2  3  1  0  0  0  0
  2 17  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  2  0  0  0  0
  6 14  1  0  0  0  0
  7  8  1  0  0  0  0
  7 15  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033291

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2

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

> <INCHI_KEY>
FPPWIEZFMZZUPL-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.431634389142875

> <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-5,13-diol

> <ALOGPS_LOGP>
2.62

> <JCHEM_LOGP>
2.2056580746666663

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.36750929598602

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.36865653546125

> <JCHEM_PKA_STRONGEST_BASIC>
-4.410363617211228

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
75.04200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.45e-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-5,13-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033291
     RDKit          3D
3,8-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.2579   -0.1546   -1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686    0.1616   -0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6469    0.2167    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.0365   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.0107   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011    0.3204    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418    0.5696    1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.5266    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136    0.7773    2.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779    0.2936    1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750   -1.1250    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121   -1.4135    1.2048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956   -0.7560    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.0911   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133   -0.4534   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236   -0.7931   -1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850    0.5398   -1.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    0.8596   -1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    0.2412   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    0.6072   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -0.2009   -0.9113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    0.4504   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1249   -1.2316   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340    0.0814   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.2846   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203    0.8142    3.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    1.0060    3.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    1.0261    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.8165    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.3413    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6686   -1.8888    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9674   -0.3072   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8522    1.0333   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339    1.6628   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.6955   -0.3713 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
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 21  5  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.927   1.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.695   0.923   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -3.695  -0.615   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -2.309  -1.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.923  -0.615   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.461  -1.077   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.385   0.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.925   0.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.541  -1.385   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.081  -1.539   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.313  -0.769   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.233  -4.003   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.617  -2.617   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.077  -2.463   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.461   1.385   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.923   0.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.309   1.693   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.309   3.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.695   4.003   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.927   3.233   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.313   4.003   0.000  0.00  0.00           O+0
CONECT    1    2   20                                                       
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7   14                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    9   12   14                                                  
CONECT   14    6   13                                                       
CONECT   15    7   16                                                       
CONECT   16    5   15   17                                                  
CONECT   17    2   16   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20    1   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0033291
HETATM    1  C1  UNL     1       5.258  -0.155  -1.452  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.969   0.162  -0.113  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.647   0.217   0.301  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.611  -0.036  -0.593  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.283   0.011  -0.211  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.001   0.320   1.102  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.042   0.570   1.978  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.367   0.527   1.613  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.414   0.777   2.494  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.478   0.294   1.215  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.875  -1.125   1.546  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.212  -1.414   1.205  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.896  -0.756   0.193  1.00  0.00           C  
HETATM   14  C11 UNL     1      -4.212  -1.091  -0.114  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.913  -0.453  -1.114  1.00  0.00           C  
HETATM   16  O4  UNL     1      -6.224  -0.793  -1.413  1.00  0.00           O  
HETATM   17  C13 UNL     1      -4.285   0.540  -1.823  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.985   0.860  -1.509  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.257   0.241  -0.515  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.880   0.607  -0.210  1.00  0.00           C  
HETATM   21  O5  UNL     1       0.079  -0.201  -0.911  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.663   0.450  -2.174  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.125  -1.232  -1.680  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.334   0.081  -1.682  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.834  -0.285  -1.642  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.820   0.814   3.014  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.292   1.006   3.451  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.866   1.026   1.942  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.231  -1.816   0.965  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.750  -1.341   2.614  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.669  -1.889   0.479  1.00  0.00           H  
HETATM   32  H11 UNL     1      -6.967  -0.307  -0.928  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.852   1.033  -2.609  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.534   1.663  -2.110  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.652   1.695  -0.371  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   21
CONECT    6    7   10
CONECT    7    8    8   26
CONECT    8    9
CONECT    9   27
CONECT   10   11   20   28
CONECT   11   12   29   30
CONECT   12   13
CONECT   13   14   14   19
CONECT   14   15   31
CONECT   15   16   17   17
CONECT   16   32
CONECT   17   18   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   21   35
END

HMDB0033291
     RDKit          3D
3,8-Dihydroxy-9-methoxypterocarpan
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.2579   -0.1546   -1.4525 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9686    0.1616   -0.1126 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6469    0.2167    0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6107   -0.0365   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2833    0.0107   -0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0011    0.3204    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0418    0.5696    1.9778 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667    0.5266    1.6134 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4136    0.7773    2.4945 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4779    0.2936    1.2147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8750   -1.1250    1.5459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2121   -1.4135    1.2048 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8956   -0.7560    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.0911   -0.1139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9133   -0.4534   -1.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2236   -0.7931   -1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2850    0.5398   -1.8228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9853    0.8596   -1.5087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2571    0.2412   -0.5146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8803    0.6072   -0.2099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -0.2009   -0.9113 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6633    0.4504   -2.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1249   -1.2316   -1.6799 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3340    0.0814   -1.6819 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.2846   -1.6418 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8203    0.8142    3.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2922    1.0060    3.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    1.0261    1.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2307   -1.8165    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.3413    2.6143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6686   -1.8888    0.4787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9674   -0.3072   -0.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8522    1.0333   -2.6091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5339    1.6628   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6523    1.6955   -0.3713 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
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 21  5  1  0
 19 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 14 31  1  0
 16 32  1  0
 17 33  1  0
 18 34  1  0
 20 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(6AR,11ar)-3,8-dihydroxy-9-methoxypterocarpan	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-5,13-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-5,13-diol

CAS Registry Number

108335-33-7

SMILES

COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

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

InChI Key

FPPWIEZFMZZUPL-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 (LMPK12070056 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0033291)
Cell membrane (HMDB: HMDB0033291)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033291)

Source

Exogenous

Exogenous (HMDB: HMDB0033291)

Food

Food (HMDB: HMDB0033291)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0033291)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0033291)

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	0.24 g/L	ALOGPS
logP	2.62	ALOGPS
logP	2.21	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.37	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	29.43 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]+	166.316	31661259
DarkChem	[M-H]-	165.82	31661259
DeepCCS	[M+H]+	165.934	30932474
DeepCCS	[M-H]-	163.576	30932474
DeepCCS	[M-2H]-	197.406	30932474
DeepCCS	[M+Na]+	172.612	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.1	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.2	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.	6.16 minutes	32390414
Predicted by Siyang on May 30, 2022	11.4233 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1763.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	263.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	151.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	144.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	558.5 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	428.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	125.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	995.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	397.7 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	1199.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	343.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	329.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	400.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	280.0 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	80.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2	3836.8	Standard polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2	2617.4	Standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan	COC1=CC2=C(C=C1O)C1COC3=C(C=CC(O)=C3)C1O2	2834.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,8-Dihydroxy-9-methoxypterocarpan,1TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1COC3=CC(O)=CC=C3C1O2	2714.0	Semi standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan,1TMS,isomer #2	COC1=CC2=C(C=C1O)C1COC3=CC(O[Si](C)(C)C)=CC=C3C1O2	2744.7	Semi standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan,2TMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C)C1COC3=CC(O[Si](C)(C)C)=CC=C3C1O2	2762.4	Semi standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan,1TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1COC3=CC(O)=CC=C3C1O2	2999.6	Semi standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan,1TBDMS,isomer #2	COC1=CC2=C(C=C1O)C1COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C1O2	3015.5	Semi standard non polar	33892256
3,8-Dihydroxy-9-methoxypterocarpan,2TBDMS,isomer #1	COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C1O2	3238.5	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 - 3,8-Dihydroxy-9-methoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ab9-0690000000-b29031c80f1bcec7583d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-7769700000-0f7f59dc99c03b4c94ea	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,8-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 - 3,8-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 - 3,8-Dihydroxy-9-methoxypterocarpan 10V, Positive-QTOF	splash10-000i-0090000000-21649f0fccde0e26a97a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 20V, Positive-QTOF	splash10-000i-0290000000-90fff769cc818ade65df	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 40V, Positive-QTOF	splash10-0pvj-9740000000-0d8dd02e1aba97a20111	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 10V, Negative-QTOF	splash10-000i-0090000000-940f1e10fca28f280a9b	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 20V, Negative-QTOF	splash10-000i-0090000000-5e55f6b5f2ab59ba7c85	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 40V, Negative-QTOF	splash10-08i9-1390000000-1f128fa06b931892c3f8	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 20V, Positive-QTOF	splash10-000i-0090000000-e3d063ae1e65953a1db2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 40V, Positive-QTOF	splash10-05tb-0790000000-478aaa827ae3f4d326e8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 20V, Negative-QTOF	splash10-000i-0090000000-a92807e25bed196d4c0f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxypterocarpan 40V, Negative-QTOF	splash10-03di-1490000000-de3a198763261a6a5571	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB011315

KNApSAcK ID

C00010006

Chemspider ID

24843003

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257449

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

3,8-Dihydroxy-9-methoxypterocarpan → 3,4,5-trihydroxy-6-({13-hydroxy-14-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaen-5-yl}oxy)oxane-2-carboxylic acid	details
3,8-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),3,5,11,13,15-hexaen-13-yl}oxy)oxane-2-carboxylic acid	details

Showing metabocard for 3,8-Dihydroxy-9-methoxypterocarpan (HMDB0033291)

MOL for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

3D MOL for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

3D SDF for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

3D-SDF for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

PDB for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

3D PDB for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

SMILES for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

INCHI for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

Structure for HMDB0033291 (3,8-Dihydroxy-9-methoxypterocarpan)

3D Structure for HMDB0033291 (3,8-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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