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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:54:39 UTC

Update Date

2022-03-07 02:53:59 UTC

HMDB ID

HMDB0034115

Secondary Accession Numbers

HMDB34115

Metabolite Identification

Common Name

6alpha-Hydroxymedicarpin

Description

(E)-4'-Methylresveratrol 3-glucoside belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton (E)-4'-Methylresveratrol 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (E)-4'-Methylresveratrol 3-glucoside has been detected, but not quantified in, green vegetables. This could make (e)-4'-methylresveratrol 3-glucoside a potential biomarker for the consumption of these foods.

Structure

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

HMDB0034115
     RDKit          3D
6alpha-Hydroxymedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.8451   -0.9726    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.5302   -0.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.7823   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.5548   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118    1.2913   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437    0.6892   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261   -0.6418   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -1.3930   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672   -0.9712   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.1901   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -0.0883   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0008   -1.2182   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2356   -1.4901   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8112   -0.6736    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0739   -0.9533    0.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.4427    0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    0.7270    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    1.8528    0.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320    1.7240    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    1.2831   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177    2.3379   -1.5670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8063   -0.7811    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906   -1.6280   -0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    0.0131   -0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946    1.0055    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218    2.3360    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861   -2.4562   -1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382    0.3776   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -1.8476   -1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907   -2.3707   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5409   -1.7867    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333    1.1034    1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452    1.0013    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    2.6987    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768    1.9564   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
M  END


  Mrv0541 05061307352D          

 21 24  0  0  0  0            999 V2000
   -0.9390   -2.2833    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
    0.5275   -1.5272    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
    5.2216   -1.2363    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
    3.1217   -0.6408    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
    0.4883   -2.3512    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
    6.4979   -1.8789    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
   -0.2450   -2.7293    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  2  2  0  0  0  0
  5  3  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  6  1  0  0  0  0
 13 11  2  0  0  0  0
 14  7  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>
HMDB0034115

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2

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

> <INCHI_KEY>
SXKBOSYKWYQHMV-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.2794

> <EXACT_MASS>
286.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.068586789054443

> <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-5,10-diol

> <ALOGPS_LOGP>
2.05

> <JCHEM_LOGP>
1.8540430143333333

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.070665661490725

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.413465455675777

> <JCHEM_PKA_STRONGEST_BASIC>
-4.094446231951658

> <JCHEM_POLAR_SURFACE_AREA>
68.15

> <JCHEM_REFRACTIVITY>
74.14900000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.82e-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-5,10-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034115
     RDKit          3D
6alpha-Hydroxymedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.8451   -0.9726    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.5302   -0.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.7823   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.5548   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118    1.2913   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437    0.6892   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261   -0.6418   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -1.3930   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672   -0.9712   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.1901   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -0.0883   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0008   -1.2182   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2356   -1.4901   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8112   -0.6736    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0739   -0.9533    0.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.4427    0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    0.7270    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    1.8528    0.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320    1.7240    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    1.2831   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177    2.3379   -1.5670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8063   -0.7811    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906   -1.6280   -0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    0.0131   -0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946    1.0055    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218    2.3360    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861   -2.4562   -1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382    0.3776   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -1.8476   -1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907   -2.3707   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5409   -1.7867    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333    1.1034    1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452    1.0013    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    2.6987    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768    1.9564   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 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      -1.753  -4.262   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.899  -4.971   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.985  -2.851   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       9.747  -2.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.207  -5.221   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      10.592  -3.595   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.911  -4.389   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      12.129  -3.507   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      -0.457  -5.095   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    4    9                                                       
CONECT    3    5   10                                                       
CONECT    4    2   11                                                       
CONECT    5    3   12                                                       
CONECT    6    9   13                                                       
CONECT    7   10   14                                                       
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    6   11   20                                                  
CONECT   14    7   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    HMDB0034115
HETATM    1  C1  UNL     1       5.845  -0.973   0.009  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.606  -1.530  -0.394  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.448  -0.782  -0.438  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.471   0.555  -0.082  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.312   1.291  -0.130  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.144   0.689  -0.531  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.126  -0.642  -0.884  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.273  -1.393  -0.842  1.00  0.00           C  
HETATM    9  O2  UNL     1      -0.167  -0.971  -1.238  1.00  0.00           O  
HETATM   10  C8  UNL     1      -0.980   0.190  -1.307  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.294  -0.088  -0.712  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.001  -1.218  -1.121  1.00  0.00           C  
HETATM   13  C11 UNL     1      -4.236  -1.490  -0.576  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.811  -0.674   0.375  1.00  0.00           C  
HETATM   15  O3  UNL     1      -6.074  -0.953   0.930  1.00  0.00           O  
HETATM   16  C13 UNL     1      -4.115   0.443   0.779  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.856   0.727   0.230  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.155   1.853   0.639  1.00  0.00           O  
HETATM   19  C15 UNL     1      -0.732   1.724   0.671  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.218   1.283  -0.658  1.00  0.00           C  
HETATM   21  O5  UNL     1      -0.118   2.338  -1.567  1.00  0.00           O  
HETATM   22  H1  UNL     1       5.806  -0.781   1.097  1.00  0.00           H  
HETATM   23  H2  UNL     1       6.691  -1.628  -0.229  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.021   0.013  -0.498  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.395   1.006   0.228  1.00  0.00           H  
HETATM   26  H5  UNL     1       2.322   2.336   0.146  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.286  -2.456  -1.119  1.00  0.00           H  
HETATM   28  H7  UNL     1      -1.138   0.378  -2.415  1.00  0.00           H  
HETATM   29  H8  UNL     1      -2.537  -1.848  -1.866  1.00  0.00           H  
HETATM   30  H9  UNL     1      -4.791  -2.371  -0.892  1.00  0.00           H  
HETATM   31  H10 UNL     1      -6.541  -1.787   0.596  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.533   1.103   1.520  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.445   1.001   1.460  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.280   2.699   0.945  1.00  0.00           H  
HETATM   35  H14 UNL     1       0.277   1.956  -2.388  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   20
CONECT    7    8    8    9
CONECT    8   27
CONECT    9   10
CONECT   10   11   20   28
CONECT   11   12   12   17
CONECT   12   13   29
CONECT   13   14   14   30
CONECT   14   15   16
CONECT   15   31
CONECT   16   17   17   32
CONECT   17   18
CONECT   18   19
CONECT   19   20   33   34
CONECT   20   21
CONECT   21   35
END

HMDB0034115
     RDKit          3D
6alpha-Hydroxymedicarpin
 35 38  0  0  0  0  0  0  0  0999 V2000
    5.8451   -0.9726    0.0094 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6058   -1.5302   -0.3941 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4479   -0.7823   -0.4383 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4714    0.5548   -0.0824 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3118    1.2913   -0.1299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1437    0.6892   -0.5305 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1261   -0.6418   -0.8835 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2735   -1.3930   -0.8424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1672   -0.9712   -1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9798    0.1901   -1.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2944   -0.0883   -0.7121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0008   -1.2182   -1.1206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2356   -1.4901   -0.5761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8112   -0.6736    0.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0739   -0.9533    0.9302 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1149    0.4427    0.7795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8564    0.7270    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1549    1.8528    0.6390 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320    1.7240    0.6709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2185    1.2831   -0.6578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177    2.3379   -1.5670 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8063   -0.7811    1.0970 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6906   -1.6280   -0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0210    0.0131   -0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3946    1.0055    0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3218    2.3360    0.1464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2861   -2.4562   -1.1189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1382    0.3776   -2.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5372   -1.8476   -1.8656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7907   -2.3707   -0.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5409   -1.7867    0.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5333    1.1034    1.5195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4452    1.0013    1.4604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2801    2.6987    0.9448 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2768    1.9564   -2.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  8  3  1  0
 20 10  1  0
 20  6  1  0
 17 11  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 16 32  1  0
 19 33  1  0
 19 34  1  0
 21 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,6a-Dihydroxy-9-methoxypterocarpan	HMDB
6a-Hydroxymedicarpin	HMDB, Generator
6Α-hydroxymedicarpin	Generator

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-5,10-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-5,10-diol

CAS Registry Number

61135-92-0

SMILES

COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2

InChI Identifier

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

InChI Key

SXKBOSYKWYQHMV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Anisole
Phenoxy compound
Phenol ether
Styrene
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Monosaccharide
Oxane
Secondary alcohol
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034115)
Cytoplasm (HMDB: HMDB0034115)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034115)

Source

Exogenous

Food

Food (HMDB: HMDB0034115)

Pulse

Pulses (FooDB: FOOD00867)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034115)
Fabaceae (HMDB: HMDB0034115)

Not Available

Nutrient (HMDB: HMDB0034115)

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	0.48 g/L	ALOGPS
logP	2.05	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.41	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	29.07 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]+	166.793	31661259
DarkChem	[M-H]-	164.17	31661259
DeepCCS	[M+H]+	168.856	30932474
DeepCCS	[M-H]-	166.498	30932474
DeepCCS	[M-2H]-	200.54	30932474
DeepCCS	[M+Na]+	175.735	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-Hydroxymedicarpin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2	3835.6	Standard polar	33892256
6alpha-Hydroxymedicarpin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2	2525.8	Standard non polar	33892256
6alpha-Hydroxymedicarpin	COC1=CC2=C(C=C1)C1(O)COC3=C(C=CC(O)=C3)C1O2	2747.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6alpha-Hydroxymedicarpin,1TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O)C=C3OCC21O[Si](C)(C)C	2586.2	Semi standard non polar	33892256
6alpha-Hydroxymedicarpin,1TMS,isomer #2	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21O	2640.6	Semi standard non polar	33892256
6alpha-Hydroxymedicarpin,2TMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C)C=C3OCC21O[Si](C)(C)C	2644.0	Semi standard non polar	33892256
6alpha-Hydroxymedicarpin,1TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O)C=C3OCC21O[Si](C)(C)C(C)(C)C	2865.2	Semi standard non polar	33892256
6alpha-Hydroxymedicarpin,1TBDMS,isomer #2	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21O	2905.3	Semi standard non polar	33892256
6alpha-Hydroxymedicarpin,2TBDMS,isomer #1	COC1=CC=C2C(=C1)OC1C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3OCC21O[Si](C)(C)C(C)(C)C	3134.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymedicarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0600-1690000000-346bdcac066b6f381678	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymedicarpin GC-MS (2 TMS) - 70eV, Positive	splash10-06fu-6629800000-b237ef9c110b76f2ec1f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymedicarpin GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6alpha-Hydroxymedicarpin 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-Hydroxymedicarpin 10V, Positive-QTOF	splash10-000i-0190000000-3d79e967ab74798677ce	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 20V, Positive-QTOF	splash10-000i-0090000000-311f4c987f635cd9a076	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 40V, Positive-QTOF	splash10-0pec-9510000000-5faf9627b9b4723bb4c1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 10V, Negative-QTOF	splash10-000i-0090000000-5f41d188549e4f62e707	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 20V, Negative-QTOF	splash10-000i-0090000000-1b1ec91bb3a5d817972c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 40V, Negative-QTOF	splash10-0670-3290000000-1831012c4879e89f261c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 10V, Negative-QTOF	splash10-000i-0090000000-14912e1703be5edd027d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 20V, Negative-QTOF	splash10-000i-0090000000-c93a26febaac60ba7a41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 40V, Negative-QTOF	splash10-0uxr-0090000000-acdcb7fb8a3e27b00b6b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 10V, Positive-QTOF	splash10-000i-0090000000-b239d41c6032c85540b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 20V, Positive-QTOF	splash10-000i-0290000000-dec61ecd14cc98e8a255	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6alpha-Hydroxymedicarpin 40V, Positive-QTOF	splash10-00y0-1940000000-4702bd8b4c2523bbaa73	2021-09-22	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

FDB012385

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751528

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-Hydroxymedicarpin (HMDB0034115)

MOL for HMDB0034115 (6alpha-Hydroxymedicarpin)

3D MOL for HMDB0034115 (6alpha-Hydroxymedicarpin)

3D SDF for HMDB0034115 (6alpha-Hydroxymedicarpin)

3D-SDF for HMDB0034115 (6alpha-Hydroxymedicarpin)

PDB for HMDB0034115 (6alpha-Hydroxymedicarpin)

3D PDB for HMDB0034115 (6alpha-Hydroxymedicarpin)

SMILES for HMDB0034115 (6alpha-Hydroxymedicarpin)

INCHI for HMDB0034115 (6alpha-Hydroxymedicarpin)

Structure for HMDB0034115 (6alpha-Hydroxymedicarpin)

3D Structure for HMDB0034115 (6alpha-Hydroxymedicarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra