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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:48:29 UTC

Update Date

2022-03-07 02:56:11 UTC

HMDB ID

HMDB0039377

Secondary Accession Numbers

HMDB39377

Metabolite Identification

Common Name

2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone

Description

2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position. Thus, 2,3',6-trihydroxy-4'-methoxybenzylcoumaranone is considered to be a flavonoid. Based on a literature review very few articles have been published on 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone.

Structure

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

HMDB0039377
     RDKit          3D
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.0622    2.0414   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815    0.7851   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.3532    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551    1.1868   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    0.7817    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -0.4528    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -0.9126    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656   -1.6489    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -2.7646   -0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.9527    0.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -0.8617    0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -0.5230    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037    0.6213    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2593    0.9678    0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    1.4452   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.1061   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5163   -0.0509   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312   -0.6617   -0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005   -0.4052   -1.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -1.2770    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.8858    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.7541    0.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0295    2.8833   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0484    2.0090   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036    2.1779   -1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332    2.1663   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.4527    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.6187    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034   -0.0613    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -2.5312   -0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -1.1563    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7537    0.4087    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299    2.3268   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    1.7284   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.2721    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -2.6509    1.1706 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  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 22 36  1  0
M  END

  Mrv0541 05061311042D          

 22 24  0  0  0  0            999 V2000
    2.1525   -3.6224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2403   -1.4985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4118   -2.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6380   -1.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -0.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533   -0.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8095   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -2.5604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -2.2634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818    0.9645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3679   -3.3674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    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
  9  8  1  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  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  7  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 16  8  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 16  1  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22 14  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039377

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-21-13-5-2-9(6-12(13)18)8-16(20)15(19)11-4-3-10(17)7-14(11)22-16/h2-7,17-18,20H,8H2,1H3

> <INCHI_KEY>
HBEFLXKTZCXMQU-UHFFFAOYSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.2788

> <EXACT_MASS>
302.07903818

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
29.763523471971332

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dihydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-3-one

> <ALOGPS_LOGP>
1.52

> <JCHEM_LOGP>
2.2686435026666665

> <ALOGPS_LOGS>
-3.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.641369502176984

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.554750774858849

> <JCHEM_PKA_STRONGEST_BASIC>
-4.681458599275505

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
77.55560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dihydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]-1-benzofuran-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039377
     RDKit          3D
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.0622    2.0414   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815    0.7851   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.3532    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551    1.1868   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    0.7817    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -0.4528    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -0.9126    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656   -1.6489    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -2.7646   -0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.9527    0.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -0.8617    0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -0.5230    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037    0.6213    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2593    0.9678    0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    1.4452   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.1061   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5163   -0.0509   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312   -0.6617   -0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005   -0.4052   -1.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -1.2770    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.8858    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.7541    0.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0295    2.8833   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0484    2.0090   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036    2.1779   -1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332    2.1663   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.4527    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.6187    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034   -0.0613    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -2.5312   -0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -1.1563    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7537    0.4087    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299    2.3268   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    1.7284   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.2721    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -2.6509    1.1706 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  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 22 36  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       4.018  -6.762   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.449  -2.797   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.769  -4.304   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.058  -2.243   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.273  -0.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.593  -1.767   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.378  -3.749   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.233  -4.779   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.788  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.842  -4.225   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.846   3.481   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.273   1.800   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.553  -6.286   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    5    9                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   13                                                       
CONECT    6    9   12                                                       
CONECT    7   10   14                                                       
CONECT    8    9   16                                                       
CONECT    9    2    6    8                                                  
CONECT   10    3    7   17                                                  
CONECT   11    4   14   15                                                  
CONECT   12    6   13   18                                                  
CONECT   13    5   12   21                                                  
CONECT   14    7   11   22                                                  
CONECT   15   11   16   19                                                  
CONECT   16    8   15   20   22                                             
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21    1   13                                                       
CONECT   22   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0039377
HETATM    1  C1  UNL     1      -5.062   2.041  -1.015  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.881   0.785  -0.426  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.635   0.353   0.003  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.555   1.187  -0.158  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.306   0.782   0.260  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.115  -0.453   0.841  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.208  -0.913   1.296  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.966  -1.649   0.211  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.306  -2.765  -0.235  1.00  0.00           O  
HETATM   10  O3  UNL     1       2.273  -1.953   0.657  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.116  -0.862   0.369  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.351  -0.523   0.845  1.00  0.00           C  
HETATM   13  C10 UNL     1       5.004   0.621   0.410  1.00  0.00           C  
HETATM   14  O4  UNL     1       6.259   0.968   0.892  1.00  0.00           O  
HETATM   15  C11 UNL     1       4.413   1.445  -0.520  1.00  0.00           C  
HETATM   16  C12 UNL     1       3.170   1.106  -1.001  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.516  -0.051  -0.557  1.00  0.00           C  
HETATM   18  C14 UNL     1       1.231  -0.662  -0.868  1.00  0.00           C  
HETATM   19  O5  UNL     1       0.500  -0.405  -1.847  1.00  0.00           O  
HETATM   20  C15 UNL     1      -2.211  -1.277   0.995  1.00  0.00           C  
HETATM   21  C16 UNL     1      -3.465  -0.886   0.582  1.00  0.00           C  
HETATM   22  O6  UNL     1      -4.558  -1.754   0.756  1.00  0.00           O  
HETATM   23  H1  UNL     1      -5.029   2.883  -0.312  1.00  0.00           H  
HETATM   24  H2  UNL     1      -6.048   2.009  -1.549  1.00  0.00           H  
HETATM   25  H3  UNL     1      -4.304   2.178  -1.822  1.00  0.00           H  
HETATM   26  H4  UNL     1      -2.633   2.166  -0.605  1.00  0.00           H  
HETATM   27  H5  UNL     1      -0.460   1.453   0.125  1.00  0.00           H  
HETATM   28  H6  UNL     1       0.102  -1.619   2.163  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.803  -0.061   1.683  1.00  0.00           H  
HETATM   30  H8  UNL     1      -0.593  -2.531  -0.516  1.00  0.00           H  
HETATM   31  H9  UNL     1       4.845  -1.156   1.583  1.00  0.00           H  
HETATM   32  H10 UNL     1       6.754   0.409   1.578  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.930   2.327  -0.848  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.687   1.728  -1.725  1.00  0.00           H  
HETATM   35  H13 UNL     1      -2.120  -2.272   1.451  1.00  0.00           H  
HETATM   36  H14 UNL     1      -4.458  -2.651   1.171  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6    6   27
CONECT    6    7   20
CONECT    7    8   28   29
CONECT    8    9   10   18
CONECT    9   30
CONECT   10   11
CONECT   11   12   12   17
CONECT   12   13   31
CONECT   13   14   15   15
CONECT   14   32
CONECT   15   16   33
CONECT   16   17   17   34
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   21   35
CONECT   21   22
CONECT   22   36
END

HMDB0039377
     RDKit          3D
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone
 36 38  0  0  0  0  0  0  0  0999 V2000
   -5.0622    2.0414   -1.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8815    0.7851   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6349    0.3532    0.0030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5551    1.1868   -0.1581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3057    0.7817    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148   -0.4528    0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081   -0.9126    1.2965 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9656   -1.6489    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3060   -2.7646   -0.2351 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2731   -1.9527    0.6567 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157   -0.8617    0.3692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3508   -0.5230    0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0037    0.6213    0.4097 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2593    0.9678    0.8923 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4134    1.4452   -0.5201 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1702    1.1061   -1.0008 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5163   -0.0509   -0.5566 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2312   -0.6617   -0.8680 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5005   -0.4052   -1.8473 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2106   -1.2770    0.9945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4652   -0.8858    0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5584   -1.7541    0.7558 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0295    2.8833   -0.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0484    2.0090   -1.5495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036    2.1779   -1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6332    2.1663   -0.6051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4605    1.4527    0.1253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1021   -1.6187    2.1634 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8034   -0.0613    1.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5931   -2.5312   -0.5158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8446   -1.1563    1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7537    0.4087    1.5778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9299    2.3268   -0.8479 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6867    1.7284   -1.7250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1195   -2.2721    1.4509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4584   -2.6509    1.1706 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  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
 18  8  1  0
 17 11  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  5 27  1  0
  7 28  1  0
  7 29  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 20 35  1  0
 22 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Molecular Weight

302.2788

Monoisotopic Molecular Weight

302.07903818

IUPAC Name

2,6-dihydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-3-one

Traditional Name

2,6-dihydroxy-2-[(3-hydroxy-4-methoxyphenyl)methyl]-1-benzofuran-3-one

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1

InChI Identifier

InChI=1S/C16H14O6/c1-21-13-5-2-9(6-12(13)18)8-16(20)15(19)11-4-3-10(17)7-14(11)22-16/h2-7,17-18,20H,8H2,1H3

InChI Key

HBEFLXKTZCXMQU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Aurone flavonoids

Sub Class

Auronols

Direct Parent

Auronols

Alternative Parents

Substituents

Auronol
Methoxyphenol
Benzofuran
Coumaran
Phenoxy compound
Anisole
Methoxybenzene
Aryl alkyl ketone
Aryl ketone
Phenol ether
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Acyloin
Ketone
Hemiacetal
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Aurone flavonoids (LMPK12130066 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039377)
Cytoplasm (HMDB: HMDB0039377)

Source

Exogenous

Exogenous (HMDB: HMDB0039377)

Food

Food (HMDB: HMDB0039377)

Endogenous

Plant

Plant (HMDB: HMDB0039377)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039377)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	196 °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	0.2 g/L	ALOGPS
logP	1.52	ALOGPS
logP	2.27	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	7.55	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	77.56 m³·mol⁻¹	ChemAxon
Polarizability	29.76 Å³	ChemAxon
Number of Rings	3	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]+	171.877	31661259
DarkChem	[M-H]-	173.875	31661259
DeepCCS	[M+H]+	175.067	30932474
DeepCCS	[M-H]-	172.709	30932474
DeepCCS	[M-2H]-	206.644	30932474
DeepCCS	[M+Na]+	182.218	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.3	32859911
AllCCS	[M+NH4]+	174.3	32859911
AllCCS	[M+Na]+	175.2	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	170.6	32859911
AllCCS	[M+HCOO]-	170.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone	COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1	4176.7	Standard polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone	COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1	2811.4	Standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone	COC1=C(O)C=C(CC2(O)OC3=C(C=CC(O)=C3)C2=O)C=C1	2804.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TMS,isomer #1	COC1=CC=C(CC2(O)OC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C	2648.4	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TMS,isomer #2	COC1=CC=C(CC2(O[Si](C)(C)C)OC3=CC(O)=CC=C3C2=O)C=C1O	2702.5	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TMS,isomer #3	COC1=CC=C(CC2(O)OC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O	2717.8	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TMS,isomer #1	COC1=CC=C(CC2(O[Si](C)(C)C)OC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C	2653.6	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TMS,isomer #2	COC1=CC=C(CC2(O)OC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C	2687.5	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TMS,isomer #3	COC1=CC=C(CC2(O[Si](C)(C)C)OC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O	2714.2	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,3TMS,isomer #1	COC1=CC=C(CC2(O[Si](C)(C)C)OC3=CC(O[Si](C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C	2708.1	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TBDMS,isomer #1	COC1=CC=C(CC2(O)OC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	2928.9	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TBDMS,isomer #2	COC1=CC=C(CC2(O[Si](C)(C)C(C)(C)C)OC3=CC(O)=CC=C3C2=O)C=C1O	3004.7	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,1TBDMS,isomer #3	COC1=CC=C(CC2(O)OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O	2995.8	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TBDMS,isomer #1	COC1=CC=C(CC2(O[Si](C)(C)C(C)(C)C)OC3=CC(O)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3187.9	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TBDMS,isomer #2	COC1=CC=C(CC2(O)OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3188.7	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,2TBDMS,isomer #3	COC1=CC=C(CC2(O[Si](C)(C)C(C)(C)C)OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O	3253.5	Semi standard non polar	33892256
2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone,3TBDMS,isomer #1	COC1=CC=C(CC2(O[Si](C)(C)C(C)(C)C)OC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C	3440.9	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 - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-2920000000-fc9708170279b4bef76f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone GC-MS (3 TMS) - 70eV, Positive	splash10-0fdx-9620120000-a6f2684653708df8414d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 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 - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 10V, Positive-QTOF	splash10-0udi-0309000000-4bb19b6a8509a4d22a7c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 20V, Positive-QTOF	splash10-0uki-0914000000-b56ddac4fc7723dbb602	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 40V, Positive-QTOF	splash10-00di-4900000000-b9dafb0c72f949bbade6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 10V, Negative-QTOF	splash10-0udi-0409000000-39ea37728243694bd699	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 20V, Negative-QTOF	splash10-0udr-0926000000-8f9cd7b17cf82a4e4c68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 40V, Negative-QTOF	splash10-014i-1900000000-99835f9761c29245a2bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 10V, Positive-QTOF	splash10-0udi-0129000000-0ebf117602d3a96d7639	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 20V, Positive-QTOF	splash10-000i-0910000000-9364681899543de3a20a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 40V, Positive-QTOF	splash10-007a-4930000000-05515966bd7aba8407ed	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 10V, Negative-QTOF	splash10-0udr-0928000000-fb4b3fe24993818113f0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 20V, Negative-QTOF	splash10-03di-0901000000-8c3c9ebcd3b014acc8ef	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone 40V, Negative-QTOF	splash10-0079-2910000000-1effe446abd48fc1ec2a	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

FDB018942

KNApSAcK ID

Not Available

Chemspider ID

24846204

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

42607789

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 2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone (HMDB0039377)

MOL for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

3D MOL for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

3D SDF for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

3D-SDF for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

PDB for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

3D PDB for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

SMILES for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

INCHI for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

Structure for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

3D Structure for HMDB0039377 (2,3',6-Trihydroxy-4'-methoxybenzylcoumaranone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra