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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:35 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034114

Secondary Accession Numbers

HMDB34114

Metabolite Identification

Common Name

6alpha-Hydroxyisomedicarpin

Description

6alpha-Hydroxyisomedicarpin 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, 6alpha-hydroxyisomedicarpin is considered to be a flavonoid lipid molecule. 6alpha-Hydroxyisomedicarpin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6alpha-hydroxyisomedicarpin has been detected, but not quantified in, fruits and pulses. This could make 6alpha-hydroxyisomedicarpin a potential biomarker for the consumption of these foods.

Structure

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

HMDB0034114
     RDKit          3D
6alpha-Hydroxyisomedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.9468   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.2202   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -0.0642   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    1.1895   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    1.3542   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    0.2490   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986   -1.0058   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -1.1642   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.1514   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6326   -2.0963   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.8634    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493   -0.8929    1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -0.4792    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -1.2093    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6901   -0.5664    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    0.8069    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245    1.4758    0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.5645    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823    0.8909    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    1.3718   -0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228    0.3078   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583    1.4341    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    1.6259   -0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0106    0.6822    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    2.0525   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.3318   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -2.1596   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -2.9702   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553   -2.1137   -1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -1.3279    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774   -2.2849    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -1.1071    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794    1.6109   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676    2.6414    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    0.1405   -1.8321 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  6  1  0
 19 13  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
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061307352D          

 21 24  0  0  0  0            999 V2000
    6.8689   -1.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5275   -1.5272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3033   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4796   -2.7100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2608   -1.1491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1823   -2.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2216   -1.2363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1217   -0.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4883   -2.3512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6743   -1.9260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0270   -2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -1.5951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3980   -1.2834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9156   -2.4191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2033   -2.0674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7507   -1.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450   -2.7293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2284   -0.7391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4979   -1.8789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9453   -0.5937    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6872   -2.7111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  2  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 10  7  2  0  0  0  0
 11  4  1  0  0  0  0
 12  5  1  0  0  0  0
 13  7  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 14 12  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 16  1  0  0  0  0
 19  1  1  0  0  0  0
 19 10  1  0  0  0  0
 20  8  1  0  0  0  0
 20 13  1  0  0  0  0
 21 14  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034114

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2

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

> <INCHI_KEY>
MENGTHFLVHDIFW-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.012262177702667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.8540430143333333

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.156502433399154

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.39614638431924

> <JCHEM_PKA_STRONGEST_BASIC>
-4.093467200520874

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
74.14900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034114
     RDKit          3D
6alpha-Hydroxyisomedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.9468   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.2202   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -0.0642   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    1.1895   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    1.3542   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    0.2490   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986   -1.0058   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -1.1642   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.1514   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6326   -2.0963   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.8634    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493   -0.8929    1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -0.4792    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -1.2093    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6901   -0.5664    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    0.8069    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245    1.4758    0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.5645    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823    0.8909    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    1.3718   -0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228    0.3078   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583    1.4341    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    1.6259   -0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0106    0.6822    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    2.0525   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.3318   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -2.1596   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -2.9702   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553   -2.1137   -1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -1.3279    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774   -2.2849    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -1.1071    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794    1.6109   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676    2.6414    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    0.1405   -1.8321 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  6  1  0
 19 13  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
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 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      12.822  -2.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.985  -2.851   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.362  -5.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.353  -2.145   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.207  -5.221   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.827  -1.196   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.911  -4.389   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.517  -3.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.649  -2.978   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.210  -2.396   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.576  -4.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.979  -3.859   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.135  -2.572   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.457  -5.095   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.160  -1.380   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.129  -3.507   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.365  -1.108   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.016  -5.061   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    5    9                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   12                                                       
CONECT    6    9   14                                                       
CONECT    7   10   13                                                       
CONECT    8   16   20                                                       
CONECT    9    2    6   17                                                  
CONECT   10    3    7   19                                                  
CONECT   11    4   13   15                                                  
CONECT   12    5   14   16                                                  
CONECT   13    7   11   20                                                  
CONECT   14    6   12   21                                                  
CONECT   15   11   16   21                                                  
CONECT   16    8   12   15   18                                             
CONECT   17    9                                                            
CONECT   18   16                                                            
CONECT   19    1   10                                                       
CONECT   20    8   13                                                       
CONECT   21   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0034114
HETATM    1  C1  UNL     1      -5.941   0.947  -0.046  1.00  0.00           C  
HETATM    2  O1  UNL     1      -5.156  -0.220  -0.215  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.773  -0.064  -0.353  1.00  0.00           C  
HETATM    4  C3  UNL     1      -3.180   1.190  -0.327  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.822   1.354  -0.462  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.033   0.249  -0.626  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.599  -1.006  -0.656  1.00  0.00           C  
HETATM    8  C7  UNL     1      -2.971  -1.164  -0.519  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.793  -2.151  -0.825  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.633  -2.096  -0.673  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.941  -0.863   0.083  1.00  0.00           C  
HETATM   12  O3  UNL     1       0.249  -0.893   1.290  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.328  -0.479   0.247  1.00  0.00           C  
HETATM   14  C11 UNL     1       3.460  -1.209   0.509  1.00  0.00           C  
HETATM   15  C12 UNL     1       4.690  -0.566   0.622  1.00  0.00           C  
HETATM   16  C13 UNL     1       4.732   0.807   0.464  1.00  0.00           C  
HETATM   17  O4  UNL     1       5.925   1.476   0.568  1.00  0.00           O  
HETATM   18  C14 UNL     1       3.591   1.565   0.198  1.00  0.00           C  
HETATM   19  C15 UNL     1       2.382   0.891   0.092  1.00  0.00           C  
HETATM   20  O5  UNL     1       1.079   1.372  -0.167  1.00  0.00           O  
HETATM   21  C16 UNL     1       0.423   0.308  -0.779  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.558   1.434   0.896  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.752   1.626  -0.900  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.011   0.682   0.059  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.842   2.053  -0.193  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.389   2.332  -0.438  1.00  0.00           H  
HETATM   27  H6  UNL     1      -3.410  -2.160  -0.543  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.998  -2.970  -0.099  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.055  -2.114  -1.694  1.00  0.00           H  
HETATM   30  H9  UNL     1       0.790  -1.328   1.977  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.477  -2.285   0.640  1.00  0.00           H  
HETATM   32  H11 UNL     1       5.604  -1.107   0.827  1.00  0.00           H  
HETATM   33  H12 UNL     1       6.479   1.611  -0.251  1.00  0.00           H  
HETATM   34  H13 UNL     1       3.668   2.641   0.081  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.725   0.140  -1.832  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   28   29
CONECT   11   12   13   21
CONECT   12   30
CONECT   13   14   14   19
CONECT   14   15   31
CONECT   15   16   16   32
CONECT   16   17   18
CONECT   17   33
CONECT   18   19   19   34
CONECT   19   20
CONECT   20   21
CONECT   21   35
END

HMDB0034114
     RDKit          3D
6alpha-Hydroxyisomedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
   -5.9405    0.9468   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1556   -0.2202   -0.2146 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7733   -0.0642   -0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1799    1.1895   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    1.3542   -0.4615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0331    0.2490   -0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5986   -1.0058   -0.6555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9709   -1.1642   -0.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7934   -2.1514   -0.8251 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6326   -2.0963   -0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9414   -0.8634    0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2493   -0.8929    1.2902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -0.4792    0.2472 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4596   -1.2093    0.5088 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6901   -0.5664    0.6216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    0.8069    0.4640 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9245    1.4758    0.5679 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5908    1.5645    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3823    0.8909    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0787    1.3718   -0.1670 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228    0.3078   -0.7788 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5583    1.4341    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7523    1.6259   -0.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0106    0.6822    0.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8418    2.0525   -0.1930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3889    2.3318   -0.4380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4099   -2.1596   -0.5428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9977   -2.9702   -0.0993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0553   -2.1137   -1.6937 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7898   -1.3279    1.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4774   -2.2849    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6039   -1.1071    0.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4794    1.6109   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676    2.6414    0.0807 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7254    0.1405   -1.8321 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  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 21 11  1  0
 21  6  1  0
 19 13  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
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 17 33  1  0
 18 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6a-Hydroxyisomedicarpin	Generator
6Α-hydroxyisomedicarpin	Generator
6a,9-Dihydroxy-3-methoxypterocarpan	HMDB

Chemical Formula

C₁₆H₁₄O₅

Average Molecular Weight

286.2794

Monoisotopic Molecular Weight

286.084123558

IUPAC Name

5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol

Traditional Name

5-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11(16),12,14-hexaene-10,14-diol

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2

InChI Identifier

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

InChI Key

MENGTHFLVHDIFW-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: HMDB0034114)
Cytoplasm (HMDB: HMDB0034114)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034114)

Source

Exogenous

Food

Food (HMDB: HMDB0034114)

Pulse

Pulses (FooDB: FOOD00867)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034114)
Fabaceae (HMDB: HMDB0034114)

Not Available

Nutrient (HMDB: HMDB0034114)

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	0.5 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-4.1	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	74.15 m³·mol⁻¹	ChemAxon
Polarizability	29.01 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]+	165.604	31661259
DarkChem	[M-H]-	167.267	31661259
DeepCCS	[M+H]+	171.998	30932474
DeepCCS	[M-H]-	169.64	30932474
DeepCCS	[M-2H]-	202.879	30932474
DeepCCS	[M+Na]+	178.105	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]-	169.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxyisomedicarpin	COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2	3791.8	Standard polar	33892256
6alpha-Hydroxyisomedicarpin	COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2	2520.9	Standard non polar	33892256
6alpha-Hydroxyisomedicarpin	COC1=CC2=C(C=C1)C1OC3=C(C=CC(O)=C3)C1(O)CO2	2741.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxyisomedicarpin,1TMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O)C3=CC=C(O[Si](C)(C)C)C=C3OC21	2636.8	Semi standard non polar	33892256
6alpha-Hydroxyisomedicarpin,1TMS,isomer #2	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC=C(O)C=C3OC21	2585.8	Semi standard non polar	33892256
6alpha-Hydroxyisomedicarpin,2TMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C)C3=CC=C(O[Si](C)(C)C)C=C3OC21	2628.9	Semi standard non polar	33892256
6alpha-Hydroxyisomedicarpin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC21	2903.0	Semi standard non polar	33892256
6alpha-Hydroxyisomedicarpin,1TBDMS,isomer #2	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC=C(O)C=C3OC21	2860.4	Semi standard non polar	33892256
6alpha-Hydroxyisomedicarpin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)OCC1(O[Si](C)(C)C(C)(C)C)C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OC21	3125.7	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 - 6alpha-Hydroxyisomedicarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ap0-1490000000-252d5b3b556c487626c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxyisomedicarpin GC-MS (2 TMS) - 70eV, Positive	splash10-06dr-9316500000-e8e2c8571d171abe1f86	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxyisomedicarpin 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 - 6alpha-Hydroxyisomedicarpin 10V, Positive-QTOF	splash10-000i-0090000000-9641d8b9a1afe1c90dd3	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Positive-QTOF	splash10-000i-0090000000-7a0980eeefa483b5b865	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Positive-QTOF	splash10-014j-9010000000-382f3c39adc712ca70a6	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Negative-QTOF	splash10-000i-0090000000-61774ec2cef1625fb2ce	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Negative-QTOF	splash10-000i-0090000000-4af9e2e3561c3950ae03	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Negative-QTOF	splash10-0699-2090000000-eeaadde5693fb0299972	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Positive-QTOF	splash10-000i-0190000000-7721aef56b8448f27f50	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Positive-QTOF	splash10-03y1-5930000000-55772c1073aa5000fc75	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 20V, Negative-QTOF	splash10-000i-0090000000-58ba825df70e2d0f5f44	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxyisomedicarpin 40V, Negative-QTOF	splash10-0fr6-3190000000-50579689b1a87df9d30a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012382

KNApSAcK ID

C00009676

Chemspider ID

24843050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44257486

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 6alpha-Hydroxyisomedicarpin (HMDB0034114)

MOL for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

3D MOL for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

3D SDF for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

3D-SDF for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

PDB for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

3D PDB for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

SMILES for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

INCHI for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

Structure for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

3D Structure for HMDB0034114 (6alpha-Hydroxyisomedicarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra