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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:29:28 UTC

Update Date

2022-03-07 02:55:15 UTC

HMDB ID

HMDB0037251

Secondary Accession Numbers

HMDB37251

Metabolite Identification

Common Name

5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone

Description

5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone has been detected, but not quantified in, herbs and spices. This could make 5,8-dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone.

Structure

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

HMDB0037251
     RDKit          3D
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.1039    0.5914    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817    1.2485    0.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506    0.5086   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -0.8550   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -1.6137   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553   -2.9863   -0.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.9549   -0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757    0.4443   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    1.1820   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303    2.5749   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    1.1235   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    0.4547   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763   -0.9322   -0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9082    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -0.1948    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232   -0.8871    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290   -0.2434    0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0652    1.1105    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911    1.7217    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937    1.8263    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872    1.1586    0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.6832   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -2.8299   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2965   -0.1971   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296    1.3268    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148    0.1376    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -1.4172    0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1140   -3.6777   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778    3.0338   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    0.2823   -2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571    1.0143   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -1.4601   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5411   -0.4005    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599   -1.9244    0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -1.9540    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537   -0.7793    0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6722    1.7807    2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    2.8920    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672    1.7332    0.9643 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
M  END


  Mrv0541 05061309402D          

 23 25  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
  9  6  1  0  0  0  0
 10  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  4  2  0  0  0  0
 11  5  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 13  2  0  0  0  0
 17 14  2  0  0  0  0
 17 16  1  0  0  0  0
 18 11  1  0  0  0  0
 19 12  1  0  0  0  0
 20 15  2  0  0  0  0
 21 16  1  0  0  0  0
 22  1  1  0  0  0  0
 22 13  1  0  0  0  0
 23  8  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037251

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O6/c1-22-13-7-12(19)14-15(20)10(8-23-17(14)16(13)21)6-9-2-4-11(18)5-3-9/h2-5,7,10,18-19,21H,6,8H2,1H3

> <INCHI_KEY>
QALFGMCBICJHPI-UHFFFAOYSA-N

> <FORMULA>
C17H16O6

> <MOLECULAR_WEIGHT>
316.3053

> <EXACT_MASS>
316.094688244

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.372657411885037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.68

> <JCHEM_LOGP>
3.014555513333333

> <ALOGPS_LOGS>
-3.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.727573145065552

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.11227818223101

> <JCHEM_PKA_STRONGEST_BASIC>
-3.835743676744344

> <JCHEM_POLAR_SURFACE_AREA>
96.22000000000001

> <JCHEM_REFRACTIVITY>
82.7407

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.48e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037251
     RDKit          3D
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.1039    0.5914    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817    1.2485    0.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506    0.5086   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -0.8550   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -1.6137   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553   -2.9863   -0.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.9549   -0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757    0.4443   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    1.1820   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303    2.5749   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    1.1235   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    0.4547   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763   -0.9322   -0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9082    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -0.1948    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232   -0.8871    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290   -0.2434    0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0652    1.1105    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911    1.7217    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937    1.8263    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872    1.1586    0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.6832   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -2.8299   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2965   -0.1971   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296    1.3268    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148    0.1376    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -1.4172    0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1140   -3.6777   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778    3.0338   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    0.2823   -2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571    1.0143   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -1.4601   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5411   -0.4005    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599   -1.9244    0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -1.9540    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537   -0.7793    0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6722    1.7807    2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    2.8920    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672    1.7332    0.9643 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   22                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   11                                                       
CONECT    5    3   11                                                       
CONECT    6    9   10                                                       
CONECT    7   12   13                                                       
CONECT    8   10   23                                                       
CONECT    9    2    3    6                                                  
CONECT   10    6    8   15                                                  
CONECT   11    4    5   18                                                  
CONECT   12    7   14   19                                                  
CONECT   13    7   16   22                                                  
CONECT   14   12   15   17                                                  
CONECT   15   10   14   20                                                  
CONECT   16   13   17   21                                                  
CONECT   17   14   16   23                                                  
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   15                                                            
CONECT   21   16                                                            
CONECT   22    1   13                                                       
CONECT   23    8   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0037251
HETATM    1  C1  UNL     1       6.104   0.591   0.569  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.882   1.249   0.208  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.751   0.509  -0.127  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.822  -0.855  -0.107  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.686  -1.614  -0.443  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.755  -2.986  -0.421  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.530  -0.955  -0.786  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.476   0.444  -0.801  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.612   1.182  -0.464  1.00  0.00           C  
HETATM   10  O3  UNL     1       2.530   2.575  -0.487  1.00  0.00           O  
HETATM   11  O4  UNL     1       0.325   1.123  -1.139  1.00  0.00           O  
HETATM   12  C8  UNL     1      -0.827   0.455  -1.537  1.00  0.00           C  
HETATM   13  C9  UNL     1      -0.976  -0.932  -0.945  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.330  -0.908   0.526  1.00  0.00           C  
HETATM   15  C11 UNL     1      -2.614  -0.195   0.681  1.00  0.00           C  
HETATM   16  C12 UNL     1      -3.823  -0.887   0.611  1.00  0.00           C  
HETATM   17  C13 UNL     1      -5.029  -0.243   0.758  1.00  0.00           C  
HETATM   18  C14 UNL     1      -5.065   1.110   0.979  1.00  0.00           C  
HETATM   19  O5  UNL     1      -6.291   1.722   1.122  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.894   1.826   1.055  1.00  0.00           C  
HETATM   21  C16 UNL     1      -2.687   1.159   0.903  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.311  -1.683  -1.159  1.00  0.00           C  
HETATM   23  O6  UNL     1       0.395  -2.830  -1.613  1.00  0.00           O  
HETATM   24  H1  UNL     1       6.297  -0.197  -0.214  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.930   1.327   0.537  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.015   0.138   1.567  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.704  -1.417   0.154  1.00  0.00           H  
HETATM   28  H5  UNL     1       2.114  -3.678  -0.600  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.678   3.034  -0.739  1.00  0.00           H  
HETATM   30  H7  UNL     1      -0.785   0.282  -2.656  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.757   1.014  -1.351  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.737  -1.460  -1.549  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.541  -0.401   1.126  1.00  0.00           H  
HETATM   34  H11 UNL     1      -1.460  -1.924   0.937  1.00  0.00           H  
HETATM   35  H12 UNL     1      -3.746  -1.954   0.434  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.954  -0.779   0.703  1.00  0.00           H  
HETATM   37  H14 UNL     1      -6.672   1.781   2.074  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.958   2.892   1.230  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.767   1.733   0.964  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3
CONECT    3    4    4    9
CONECT    4    5   27
CONECT    5    6    7    7
CONECT    6   28
CONECT    7    8   22
CONECT    8    9    9   11
CONECT    9   10
CONECT   10   29
CONECT   11   12
CONECT   12   13   30   31
CONECT   13   14   22   32
CONECT   14   15   33   34
CONECT   15   16   16   21
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   20
CONECT   19   37
CONECT   20   21   21   38
CONECT   21   39
CONECT   22   23   23
END

HMDB0037251
     RDKit          3D
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone
 39 41  0  0  0  0  0  0  0  0999 V2000
    6.1039    0.5914    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8817    1.2485    0.2080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7506    0.5086   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8218   -0.8550   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6859   -1.6137   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7553   -2.9863   -0.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5297   -0.9549   -0.7860 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4757    0.4443   -0.8006 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    1.1820   -0.4637 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5303    2.5749   -0.4868 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3255    1.1235   -1.1394 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8270    0.4547   -1.5374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9763   -0.9322   -0.9455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3304   -0.9082    0.5258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6142   -0.1948    0.6806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8232   -0.8871    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290   -0.2434    0.7579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0652    1.1105    0.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2911    1.7217    1.1222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8937    1.8263    1.0546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6872    1.1586    0.9033 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3108   -1.6832   -1.1590 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3951   -2.8299   -1.6130 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2965   -0.1971   -0.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9296    1.3268    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0148    0.1376    1.5668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7039   -1.4172    0.1540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1140   -3.6777   -0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778    3.0338   -0.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855    0.2823   -2.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7571    1.0143   -1.3508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7369   -1.4601   -1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5411   -0.4005    1.1264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4599   -1.9244    0.9372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7458   -1.9540    0.4343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9537   -0.7793    0.7034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6722    1.7807    2.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9585    2.8920    1.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672    1.7332    0.9643 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  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  2  0
 13 22  1  0
 22 23  2  0
  9  3  1  0
 21 15  1  0
 22  7  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  6 28  1  0
 10 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-O-Demethyl-7-O-methyl-3,9-dihydropunctatin	HMDB

Chemical Formula

C₁₇H₁₆O₆

Average Molecular Weight

316.3053

Monoisotopic Molecular Weight

316.094688244

IUPAC Name

5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

5,8-dihydroxy-3-[(4-hydroxyphenyl)methyl]-7-methoxy-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

93078-83-2

SMILES

COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2

InChI Identifier

InChI=1S/C17H16O6/c1-22-13-7-12(19)14-15(20)10(8-23-17(14)16(13)21)6-9-2-4-11(18)5-3-9/h2-5,7,10,18-19,21H,6,8H2,1H3

InChI Key

QALFGMCBICJHPI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Homoisoflavonoids

Sub Class

Homoisoflavans

Direct Parent

Homoisoflavanones

Alternative Parents

Substituents

Homoisoflavanone
Chromone
Chromane
Benzopyran
1-benzopyran
Anisole
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Ether
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0037251)

Cellular substructure

Membrane (HMDB: HMDB0037251)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037251)

Source

Exogenous

Food

Food (HMDB: HMDB0037251)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037251)

Not Available

Nutrient (HMDB: HMDB0037251)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	172 - 174 °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	0.085 g/L	ALOGPS
logP	2.68	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-3.8	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	82.74 m³·mol⁻¹	ChemAxon
Polarizability	31.37 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]+	172.931	31661259
DarkChem	[M-H]-	171.643	31661259
DeepCCS	[M+H]+	172.921	30932474
DeepCCS	[M-H]-	170.563	30932474
DeepCCS	[M-2H]-	204.642	30932474
DeepCCS	[M+Na]+	179.869	30932474
AllCCS	[M+H]+	174.5	32859911
AllCCS	[M+H-H2O]+	171.0	32859911
AllCCS	[M+NH4]+	177.7	32859911
AllCCS	[M+Na]+	178.6	32859911
AllCCS	[M-H]-	175.8	32859911
AllCCS	[M+Na-2H]-	175.3	32859911
AllCCS	[M+HCOO]-	175.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone	COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	4273.7	Standard polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone	COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	3048.9	Standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone	COC1=C(O)C2=C(C(O)=C1)C(=O)C(CC1=CC=C(O)C=C1)CO2	3050.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TMS,isomer #1	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O[Si](C)(C)C	2900.7	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TMS,isomer #2	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O	2966.0	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TMS,isomer #3	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1O	2917.0	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O[Si](C)(C)C	2882.2	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TMS,isomer #2	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1O[Si](C)(C)C	2886.8	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TMS,isomer #3	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1O	2934.0	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,3TMS,isomer #1	COC1=CC(O[Si](C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C)C=C3)COC2=C1O[Si](C)(C)C	2913.1	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TBDMS,isomer #1	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O[Si](C)(C)C(C)(C)C	3160.3	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TBDMS,isomer #2	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O	3213.4	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,1TBDMS,isomer #3	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1O	3193.5	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O)C=C3)COC2=C1O[Si](C)(C)C(C)(C)C	3361.3	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TBDMS,isomer #2	COC1=CC(O)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1O[Si](C)(C)C(C)(C)C	3370.8	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,2TBDMS,isomer #3	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1O	3435.0	Semi standard non polar	33892256
5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone,3TBDMS,isomer #1	COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C(CC3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3)COC2=C1O[Si](C)(C)C(C)(C)C	3602.4	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 - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1961000000-2ce94aeb0e75a8674c8c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone GC-MS (3 TMS) - 70eV, Positive	splash10-014i-1900460000-8ab2d4ef655b65f5b02b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 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 - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 10V, Positive-QTOF	splash10-0159-0927000000-231473ad4113109ac352	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 20V, Positive-QTOF	splash10-053r-0921000000-426d6dff7caa1c50b8b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 40V, Positive-QTOF	splash10-0a7i-1900000000-363f5f99eb7c163493c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 10V, Negative-QTOF	splash10-014i-0619000000-15ed5e4c6e7457711b77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 20V, Negative-QTOF	splash10-0ldi-0953000000-27d3d8b89b62665e4b11	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 40V, Negative-QTOF	splash10-007c-2920000000-3e8934bef3b8f11038c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 10V, Positive-QTOF	splash10-014i-0009000000-9d41b4964537964e8e8b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 20V, Positive-QTOF	splash10-014i-0139000000-53137a6470c1a89b1261	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 40V, Positive-QTOF	splash10-0a5i-1910000000-12fa679fd073f731cd4a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 10V, Negative-QTOF	splash10-014i-0009000000-a5811c0f9e3fc0f9d174	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 20V, Negative-QTOF	splash10-0lea-0193000000-5181d2455f48ca8af70e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone 40V, Negative-QTOF	splash10-0002-4940000000-ba047e02e1d481869213	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016262

KNApSAcK ID

C00054438

Chemspider ID

10254759

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14159173

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 5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone (HMDB0037251)

MOL for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

3D MOL for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

3D SDF for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

3D-SDF for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

PDB for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

3D PDB for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

SMILES for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

INCHI for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

Structure for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

3D Structure for HMDB0037251 (5,8-Dihydroxy-3-(4-hydroxybenzyl)-7-methoxy-4-chromanone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra