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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:46:39 UTC

Update Date

2022-03-07 02:53:57 UTC

HMDB ID

HMDB0034002

Secondary Accession Numbers

HMDB34002

Metabolite Identification

Common Name

3,4,9-Trihydroxypterocarpan

Description

3,4,9-Trihydroxypterocarpan, also known as 4-hydroxydemethylmedicarpin, 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, 3,4,9-trihydroxypterocarpan is considered to be a flavonoid lipid molecule. 3,4,9-Trihydroxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3,4,9-trihydroxypterocarpan has been detected, but not quantified in, a few different foods, such as alfalfa, herbs and spices, and pulses. This could make 3,4,9-trihydroxypterocarpan a potential biomarker for the consumption of these foods.

Structure

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

HMDB0034002
     RDKit          3D
3,4,9-Trihydroxypterocarpan
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.5477   -0.2878    1.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -0.1281    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    0.1535   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.3143   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639    0.1974   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0795    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275   -0.2354    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830   -0.1470    1.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.7089    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.5284    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.3043    0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263    1.1384    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3097    0.1920    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6818   -0.0316    0.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -0.6003   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0440   -1.5633   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.4135   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278   -1.1993   -1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715   -1.0698   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    0.3103   -1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918   -1.1938    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    0.2470   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381    0.5317   -2.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -0.4577    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    1.7383    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    2.0719    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.7425    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3452    0.4927    0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -2.1156   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -1.4460   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810   -1.7562   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    1.0533   -1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 20  9  1  0
 20  5  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 19 31  1  0
 20 32  1  0
M  END


  Mrv0541 05061307292D          

 20 23  0  0  0  0            999 V2000
    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
    6.5246    2.4062    0.0000 O   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
    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
  2  1  2  0  0  0  0
  4  3  2  0  0  0  0
  7  1  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 12  8  2  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15  9  2  0  0  0  0
 15 13  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 18 13  1  0  0  0  0
 19  6  1  0  0  0  0
 19 15  1  0  0  0  0
 20 12  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034002

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-7-1-2-8-10-6-19-15-9(3-4-11(17)13(15)18)14(10)20-12(8)5-7/h1-5,10,14,16-18H,6H2

> <INCHI_KEY>
CLHTZHIBHTWFEM-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.026628268653816

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.87

> <JCHEM_LOGP>
2.059764018666666

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.811778317015424

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.205380611419981

> <JCHEM_PKA_STRONGEST_BASIC>
-4.620187150767641

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
70.5597

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.39e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034002
     RDKit          3D
3,4,9-Trihydroxypterocarpan
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.5477   -0.2878    1.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -0.1281    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    0.1535   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.3143   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639    0.1974   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0795    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275   -0.2354    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830   -0.1470    1.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.7089    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.5284    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.3043    0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263    1.1384    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3097    0.1920    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6818   -0.0316    0.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -0.6003   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0440   -1.5633   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.4135   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278   -1.1993   -1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715   -1.0698   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    0.3103   -1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918   -1.1938    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    0.2470   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381    0.5317   -2.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -0.4577    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    1.7383    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    2.0719    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.7425    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3452    0.4927    0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -2.1156   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -1.4460   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810   -1.7562   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    1.0533   -1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 20  9  1  0
 20  5  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 19 31  1  0
 20 32  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.737   2.247   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.368   1.542   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.360   4.456   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.822   4.367   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.515   4.618   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.895   0.593   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.810   3.786   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.073   2.374   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.205   3.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.587   1.969   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.130   2.992   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.146   3.913   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.975   1.704   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.742   3.256   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.512   1.793   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.179   4.492   0.000  0.00  0.00           O+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       4.357   0.505   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.706   4.457   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    8                                                       
CONECT    3    4    9                                                       
CONECT    4    3   11                                                       
CONECT    5    7   12                                                       
CONECT    6   10   19                                                       
CONECT    7    1    5   16                                                  
CONECT    8    2   10   12                                                  
CONECT    9    3   14   15                                                  
CONECT   10    6    8   14                                                  
CONECT   11    4   13   17                                                  
CONECT   12    5    8   20                                                  
CONECT   13   11   15   18                                                  
CONECT   14    9   10   20                                                  
CONECT   15    9   13   19                                                  
CONECT   16    7                                                            
CONECT   17   11                                                            
CONECT   18   13                                                            
CONECT   19    6   15                                                       
CONECT   20   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

COMPND    HMDB0034002
HETATM    1  O1  UNL     1       5.548  -0.288   1.404  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.359  -0.128   0.718  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.330   0.154  -0.645  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.161   0.314  -1.337  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.964   0.197  -0.682  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.928  -0.079   0.662  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.128  -0.235   1.329  1.00  0.00           C  
HETATM    8  O2  UNL     1       0.583  -0.147   1.089  1.00  0.00           O  
HETATM    9  C7  UNL     1      -0.113   0.709   0.193  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.547   0.528   0.187  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.350   1.304   0.987  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.726   1.138   0.988  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.310   0.192   0.186  1.00  0.00           C  
HETATM   14  O3  UNL     1      -5.682  -0.032   0.134  1.00  0.00           O  
HETATM   15  C12 UNL     1      -3.510  -0.600  -0.629  1.00  0.00           C  
HETATM   16  O4  UNL     1      -4.044  -1.563  -1.451  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.143  -0.414  -0.609  1.00  0.00           C  
HETATM   18  O5  UNL     1      -1.328  -1.199  -1.419  1.00  0.00           O  
HETATM   19  C14 UNL     1       0.072  -1.070  -1.469  1.00  0.00           C  
HETATM   20  C15 UNL     1       0.558   0.310  -1.125  1.00  0.00           C  
HETATM   21  H1  UNL     1       5.992  -1.194   1.493  1.00  0.00           H  
HETATM   22  H2  UNL     1       5.269   0.247  -1.167  1.00  0.00           H  
HETATM   23  H3  UNL     1       3.238   0.532  -2.396  1.00  0.00           H  
HETATM   24  H4  UNL     1       3.129  -0.458   2.406  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.226   1.738   0.431  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.932   2.072   1.644  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.378   1.742   1.614  1.00  0.00           H  
HETATM   28  H8  UNL     1      -6.345   0.493   0.687  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.426  -2.116  -2.026  1.00  0.00           H  
HETATM   30  H10 UNL     1       0.474  -1.446  -2.423  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.481  -1.756  -0.670  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.396   1.053  -1.911  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3    7
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   20
CONECT    6    7    7    8
CONECT    7   24
CONECT    8    9
CONECT    9   10   20   25
CONECT   10   11   11   17
CONECT   11   12   26
CONECT   12   13   13   27
CONECT   13   14   15
CONECT   14   28
CONECT   15   16   17   17
CONECT   16   29
CONECT   17   18
CONECT   18   19
CONECT   19   20   30   31
CONECT   20   32
END

HMDB0034002
     RDKit          3D
3,4,9-Trihydroxypterocarpan
 32 35  0  0  0  0  0  0  0  0999 V2000
    5.5477   -0.2878    1.4039 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3589   -0.1281    0.7181 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3300    0.1535   -0.6445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1606    0.3143   -1.3369 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9639    0.1974   -0.6818 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9275   -0.0795    0.6623 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1275   -0.2354    1.3291 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830   -0.1470    1.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1129    0.7089    0.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5473    0.5284    0.1873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3499    1.3043    0.9870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7263    1.1384    0.9880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3097    0.1920    0.1860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6818   -0.0316    0.1335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5099   -0.6003   -0.6285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0440   -1.5633   -1.4512 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1432   -0.4135   -0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3278   -1.1993   -1.4195 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0715   -1.0698   -1.4686 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5579    0.3103   -1.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9918   -1.1938    1.4932 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694    0.2470   -1.1669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2381    0.5317   -2.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1290   -0.4577    2.4059 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    1.7383    0.4305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9315    2.0719    1.6436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3775    1.7425    1.6136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3452    0.4927    0.6874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4263   -2.1156   -2.0256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4736   -1.4460   -2.4227 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4810   -1.7562   -0.6705 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3957    1.0533   -1.9106 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  7  2  1  0
 20  9  1  0
 20  5  1  0
 17 10  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 19 30  1  0
 19 31  1  0
 20 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4',7,8-Trihydroxypterocarpan	HMDB
4-Hydroxydemethylmedicarpin	HMDB
6a,11a-Dihydro-6H-benzofuro[3,2-c][1]benzopyran-3,4,9-triol	HMDB

Chemical Formula

C₁₅H₁₂O₅

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

IUPAC Name

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

Traditional Name

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

CAS Registry Number

61255-58-1

SMILES

OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2

InChI Identifier

InChI=1S/C15H12O5/c16-7-1-2-8-10-6-19-15-9(3-4-11(17)13(15)18)14(10)20-12(8)5-7/h1-5,10,14,16-18H,6H2

InChI Key

CLHTZHIBHTWFEM-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

Not Available

Substituents

Not Available

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034002)
Cytoplasm (HMDB: HMDB0034002)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034002)

Source

Exogenous

Food

Food (HMDB: HMDB0034002)

Herb and spice

Herb

Alfalfa (FooDB: FOOD00286)

Herbs and Spices (FooDB: FOOD00866)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0034002)
Fabaceae (HMDB: HMDB0034002)

Not Available

Nutrient (HMDB: HMDB0034002)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118 - 120 °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	0.34 g/L	ALOGPS
logP	1.87	ALOGPS
logP	2.06	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.56 m³·mol⁻¹	ChemAxon
Polarizability	27.03 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]+	160.091	31661259
DarkChem	[M-H]-	161.361	31661259
DeepCCS	[M+H]+	163.316	30932474
DeepCCS	[M-H]-	160.958	30932474
DeepCCS	[M-2H]-	194.355	30932474
DeepCCS	[M+Na]+	169.543	30932474
AllCCS	[M+H]+	162.8	32859911
AllCCS	[M+H-H2O]+	158.9	32859911
AllCCS	[M+NH4]+	166.3	32859911
AllCCS	[M+Na]+	167.3	32859911
AllCCS	[M-H]-	165.0	32859911
AllCCS	[M+Na-2H]-	164.2	32859911
AllCCS	[M+HCOO]-	163.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3,4,9-Trihydroxypterocarpan	OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	3823.1	Standard polar	33892256
3,4,9-Trihydroxypterocarpan	OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	2598.2	Standard non polar	33892256
3,4,9-Trihydroxypterocarpan	OC1=CC2=C(C=C1)C1COC3=C(C=CC(O)=C3O)C1O2	2798.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,4,9-Trihydroxypterocarpan,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O)=C3OCC21	2738.7	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1O)OCC1C3=CC=C(O)C=C3OC21	2733.7	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,1TMS,isomer #3	C[Si](C)(C)OC1=C(O)C=CC2=C1OCC1C3=CC=C(O)C=C3OC21	2696.2	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O)=C3OCC21	2750.9	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C)=C3OCC21	2673.2	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C)OCC1C3=CC=C(O)C=C3OC21	2691.2	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3OCC21	2756.3	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O)=C3OCC21	3008.6	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O)OCC1C3=CC=C(O)C=C3OC21	3011.1	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=C1OCC1C3=CC=C(O)C=C3OC21	2960.8	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3OCC21	3254.8	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3201.7	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1O[Si](C)(C)C(C)(C)C)OCC1C3=CC=C(O)C=C3OC21	3204.1	Semi standard non polar	33892256
3,4,9-Trihydroxypterocarpan,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3OCC21	3430.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-0590000000-e87e687c9d5d29f4117c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (3 TMS) - 70eV, Positive	splash10-00di-3311900000-340d92eaac710fedbd00	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3,4,9-Trihydroxypterocarpan 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 - 3,4,9-Trihydroxypterocarpan 10V, Positive-QTOF	splash10-00fr-0590000000-01a2e141d58a0ced037a	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Positive-QTOF	splash10-00fr-0790000000-7b6ab35af293767c3f61	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Positive-QTOF	splash10-014i-9400000000-fe734ecfab3d19f102ae	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Negative-QTOF	splash10-00di-0090000000-0574861281df14e569ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Negative-QTOF	splash10-00di-0190000000-dc0deab378678379a9bc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Negative-QTOF	splash10-0a5a-1920000000-50df59a1fcb4e08391a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Positive-QTOF	splash10-00di-0090000000-031a5312b116bdf1aa4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Positive-QTOF	splash10-00di-0590000000-8a0ac518db1ed0cf99da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Positive-QTOF	splash10-0002-1920000000-723ef1d5667e389b44ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 10V, Negative-QTOF	splash10-00di-0090000000-d6b6f6391b4e9f4522f4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 20V, Negative-QTOF	splash10-00di-0190000000-4ac4f4ac12a68204cc12	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,4,9-Trihydroxypterocarpan 40V, Negative-QTOF	splash10-0gdi-1490000000-af76e31dafa528327445	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012236

KNApSAcK ID

C00009612

Chemspider ID

24843014

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257457

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 3,4,9-Trihydroxypterocarpan (HMDB0034002)

MOL for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

3D MOL for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

3D SDF for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

3D-SDF for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

PDB for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

3D PDB for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

SMILES for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

INCHI for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

Structure for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

3D Structure for HMDB0034002 (3,4,9-Trihydroxypterocarpan)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra