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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:15 UTC

Update Date

2022-03-07 02:52:42 UTC

HMDB ID

HMDB0030823

Secondary Accession Numbers

HMDB30823

Metabolite Identification

Common Name

Afzelechin

Description

Afzelechin is a flavan-3-ol, a type of flavonoid. It exists as at least 2 major epimers (afzelechin and epi-afzelechin). It is produced through the transformation of cis-3,4lecuopelargonidin through the action of (2R,3S)-catechin:NADP+ 4-oxidoreductase. Afzelechin can be found in many plants native to Asia such as: Astilbe rivularis (also known as waterside astilbe), Bergenia ligulate (also known as Paashaanbhed in Ayurveda traditional Indian medicine), and Wisteria floribunda (Japanese wisteria). Afzelechin also occurs in barley and rye as a member of the proanthocyanidins found in these crop plants. Afzelechin exhibits moderate inhibitory effects on tumor necrosis factor alpha (TNF-α) induced nuclear factor kappa-B (NF-kB) activation in HepG2 cells (PMID: 21985227 ). Afzelechin is only found in individuals who have consumed barley/rye or taken certain herbal medicines containing this compound.

Structure

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

HMDB0030823
     RDKit          3D
Afzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9504    0.7730    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    0.5328    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253    0.9185    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.6392    0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.0063   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.2822   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    0.8939   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    0.8626   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    2.0167   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7045    2.0059   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231    3.1705   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8090    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.3406    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460   -1.5398    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.3059    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.5338    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -1.4645    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427   -2.6735   -0.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.3677   -1.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3009   -0.1197   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689    0.0777    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    1.4195    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    0.9340    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.5221   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249    2.9117   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    3.2561   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3733    0.7592    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -2.3653    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.9510    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -2.3265   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -1.4580    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -3.4295   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084   -0.8724   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760   -0.4213   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END


  Mrv0541 05061305322D          

 20 22  0  0  0  0            999 V2000
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12 11  2  0  0  0  0
 13  7  1  0  0  0  0
 14  6  2  0  0  0  0
 14 11  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030823

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2

> <INCHI_KEY>
RSYUFYQTACJFML-UHFFFAOYSA-N

> <FORMULA>
C15H14O5

> <MOLECULAR_WEIGHT>
274.2687

> <EXACT_MASS>
274.084123558

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
27.456820357249484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
2.098672337

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.732353998993323

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.149760394378264

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2843440587393635

> <JCHEM_POLAR_SURFACE_AREA>
90.15

> <JCHEM_REFRACTIVITY>
72.01880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5,7,4'-tetrahydroxyflavan

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0030823
     RDKit          3D
Afzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9504    0.7730    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    0.5328    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253    0.9185    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.6392    0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.0063   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.2822   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    0.8939   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    0.8626   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    2.0167   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7045    2.0059   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231    3.1705   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8090    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.3406    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460   -1.5398    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.3059    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.5338    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -1.4645    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427   -2.6735   -0.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.3677   -1.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3009   -0.1197   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689    0.0777    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    1.4195    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    0.9340    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.5221   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249    2.9117   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    3.2561   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3733    0.7592    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -2.3653    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.9510    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -2.3265   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -1.4580    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -3.4295   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084   -0.8724   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760   -0.4213   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  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       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      12.003  -5.390   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2    9                                                       
CONECT    5   10   12                                                       
CONECT    6   10   14                                                       
CONECT    7   11   13                                                       
CONECT    8    1    2   15                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    7   12   14                                                  
CONECT   12    5   11   18                                                  
CONECT   13    7   15   19                                                  
CONECT   14    6   11   20                                                  
CONECT   15    8   13   20                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0030823
HETATM    1  O1  UNL     1       5.950   0.773   0.416  1.00  0.00           O  
HETATM    2  C1  UNL     1       4.594   0.533   0.177  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.625   0.918   1.068  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.312   0.639   0.747  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.956  -0.006  -0.424  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.513  -0.282  -0.717  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.196   0.894  -0.415  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.569   0.863  -0.269  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.335   2.017  -0.482  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.704   2.006  -0.340  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.423   3.171  -0.561  1.00  0.00           O  
HETATM   12  C9  UNL     1      -4.283   0.809   0.019  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.567  -0.341   0.236  1.00  0.00           C  
HETATM   14  O4  UNL     1      -4.146  -1.540   0.597  1.00  0.00           O  
HETATM   15  C11 UNL     1      -2.182  -0.306   0.088  1.00  0.00           C  
HETATM   16  C12 UNL     1      -1.424  -1.534   0.320  1.00  0.00           C  
HETATM   17  C13 UNL     1       0.028  -1.465   0.055  1.00  0.00           C  
HETATM   18  O5  UNL     1       0.443  -2.673  -0.546  1.00  0.00           O  
HETATM   19  C14 UNL     1       2.968  -0.368  -1.275  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.301  -0.120  -1.018  1.00  0.00           C  
HETATM   21  H1  UNL     1       6.469   0.078   0.903  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.931   1.419   1.973  1.00  0.00           H  
HETATM   23  H3  UNL     1       1.550   0.934   1.432  1.00  0.00           H  
HETATM   24  H4  UNL     1       0.449  -0.522  -1.797  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.825   2.912  -0.759  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.408   3.256  -0.483  1.00  0.00           H  
HETATM   27  H7  UNL     1      -5.373   0.759   0.142  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.588  -2.365   0.750  1.00  0.00           H  
HETATM   29  H9  UNL     1      -1.628  -1.951   1.357  1.00  0.00           H  
HETATM   30  H10 UNL     1      -1.880  -2.327  -0.353  1.00  0.00           H  
HETATM   31  H11 UNL     1       0.559  -1.458   1.046  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.101  -3.430  -0.028  1.00  0.00           H  
HETATM   33  H13 UNL     1       2.708  -0.872  -2.195  1.00  0.00           H  
HETATM   34  H14 UNL     1       5.076  -0.421  -1.717  1.00  0.00           H  
CONECT    1    2   21
CONECT    2    3    3   20
CONECT    3    4   22
CONECT    4    5    5   23
CONECT    5    6   19
CONECT    6    7   17   24
CONECT    7    8
CONECT    8    9    9   15
CONECT    9   10   25
CONECT   10   11   12   12
CONECT   11   26
CONECT   12   13   27
CONECT   13   14   15   15
CONECT   14   28
CONECT   15   16
CONECT   16   17   29   30
CONECT   17   18   31
CONECT   18   32
CONECT   19   20   20   33
CONECT   20   34
END

HMDB0030823
     RDKit          3D
Afzelechin
 34 36  0  0  0  0  0  0  0  0999 V2000
    5.9504    0.7730    0.4163 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5942    0.5328    0.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253    0.9185    1.0678 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3124    0.6392    0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9560   -0.0063   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5130   -0.2822   -0.7170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1965    0.8939   -0.4155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5688    0.8626   -0.2687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3351    2.0167   -0.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7045    2.0059   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4231    3.1705   -0.5610 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2831    0.8090    0.0194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5669   -0.3406    0.2365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460   -1.5398    0.5972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1821   -0.3059    0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4243   -1.5338    0.3198 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0277   -1.4645    0.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4427   -2.6735   -0.5460 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9680   -0.3677   -1.2752 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3009   -0.1197   -1.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4689    0.0777    0.9034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9307    1.4195    1.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    0.9340    1.4317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4486   -0.5221   -1.7975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8249    2.9117   -0.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4079    3.2561   -0.4829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3733    0.7592    0.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5884   -2.3653    0.7498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6279   -1.9510    1.3568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8798   -2.3265   -0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5588   -1.4580    1.0459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011   -3.4295   -0.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7084   -0.8724   -2.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0760   -0.4213   -1.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
  5 19  1  0
 19 20  2  0
 20  2  1  0
 17  6  1  0
 15  8  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  9 25  1  0
 11 26  1  0
 12 27  1  0
 14 28  1  0
 16 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
 20 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-3,4',5,7-Flaventetrol	HMDB
(+)-Afzelechin	HMDB
3,5,7,4'-Tetrahydroxyflavan	HMDB

Chemical Formula

C₁₅H₁₄O₅

Average Molecular Weight

274.2687

Monoisotopic Molecular Weight

274.084123558

IUPAC Name

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

Traditional Name

3,5,7,4'-tetrahydroxyflavan

CAS Registry Number

2545-00-8

SMILES

OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C15H14O5/c16-9-3-1-8(2-4-9)15-13(19)7-11-12(18)5-10(17)6-14(11)20-15/h1-6,13,15-19H,7H2

InChI Key

RSYUFYQTACJFML-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavan-3-ols. These are flavans that bear and hydroxyl group at position 3 (B ring), but not at position 4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavan-3-ols

Alternative Parents

Substituents

3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
1-benzopyran
Chromane
Benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Ether
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

a 2,3-<i>trans</i>-flavan-3-ol (CPD-1962 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	221 - 222 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	8200 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	1.29	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.15	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	90.15 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.02 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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]+	165.045	31661259
DarkChem	[M-H]-	163.74	31661259
DeepCCS	[M+H]+	164.779	30932474
DeepCCS	[M-H]-	162.421	30932474
DeepCCS	[M-2H]-	195.307	30932474
DeepCCS	[M+Na]+	170.872	30932474
AllCCS	[M+H]+	164.9	32859911
AllCCS	[M+H-H2O]+	161.1	32859911
AllCCS	[M+NH4]+	168.5	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	164.6	32859911
AllCCS	[M+Na-2H]-	164.1	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.35 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0858 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.46 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	42.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1382.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	230.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	122.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	150.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	109.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	433.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	349.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	371.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	687.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	319.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1083.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	249.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	257.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	438.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	342.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	132.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Afzelechin	OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1	4385.2	Standard polar	33892256
Afzelechin	OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1	2909.9	Standard non polar	33892256
Afzelechin	OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1	2974.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Afzelechin,1TMS,isomer #1	C[Si](C)(C)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1	2812.6	Semi standard non polar	33892256
Afzelechin,1TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=CC2=C1CC(O)C(C1=CC=C(O)C=C1)O2	2866.3	Semi standard non polar	33892256
Afzelechin,1TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2CC(O)C(C3=CC=C(O)C=C3)OC2=C1	2885.3	Semi standard non polar	33892256
Afzelechin,1TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O)C=C1	2887.5	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=CC2=C1CC(O[Si](C)(C)C)C(C1=CC=C(O)C=C1)O2	2846.7	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2CC(O[Si](C)(C)C)C(C3=CC=C(O)C=C3)OC2=C1	2855.9	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C)C=C1	2865.2	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #4	C[Si](C)(C)OC1=CC2=C(CC(O)C(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2871.1	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #5	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O)C=C1	2860.8	Semi standard non polar	33892256
Afzelechin,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O)C=C1	2871.5	Semi standard non polar	33892256
Afzelechin,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(CC(O[Si](C)(C)C)C(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C)=C1	2771.3	Semi standard non polar	33892256
Afzelechin,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1	2751.9	Semi standard non polar	33892256
Afzelechin,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C)C=C1	2724.4	Semi standard non polar	33892256
Afzelechin,3TMS,isomer #4	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O)C=C1	2851.2	Semi standard non polar	33892256
Afzelechin,4TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3CC2O[Si](C)(C)C)C=C1	2771.1	Semi standard non polar	33892256
Afzelechin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1CC2=C(O)C=C(O)C=C2OC1C1=CC=C(O)C=C1	3125.4	Semi standard non polar	33892256
Afzelechin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1CC(O)C(C1=CC=C(O)C=C1)O2	3128.5	Semi standard non polar	33892256
Afzelechin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2CC(O)C(C3=CC=C(O)C=C3)OC2=C1	3153.8	Semi standard non polar	33892256
Afzelechin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O)C=C1	3156.1	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1CC(O[Si](C)(C)C(C)(C)C)C(C1=CC=C(O)C=C1)O2	3405.8	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2CC(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O)C=C3)OC2=C1	3413.8	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1	3429.9	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC2=C(CC(O)C(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3367.5	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1	3389.1	Semi standard non polar	33892256
Afzelechin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O)C=C1	3391.4	Semi standard non polar	33892256
Afzelechin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(CC(O[Si](C)(C)C(C)(C)C)C(C3=CC=C(O)C=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C1	3490.8	Semi standard non polar	33892256
Afzelechin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1	3525.3	Semi standard non polar	33892256
Afzelechin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1	3501.8	Semi standard non polar	33892256
Afzelechin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O)C=C1	3553.6	Semi standard non polar	33892256
Afzelechin,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2OC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3CC2O[Si](C)(C)C(C)(C)C)C=C1	3649.8	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 - Afzelechin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1970000000-3e9c0c6abe4a7d16da50	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Afzelechin GC-MS (4 TMS) - 70eV, Positive	splash10-002b-3700890000-ad3a8c90f22f6dcef7bc	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Afzelechin 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 - Afzelechin 10V, Positive-QTOF	splash10-004i-0490000000-0ddff31e344d18cb951d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Positive-QTOF	splash10-000i-0920000000-369f0cf2ba40b21ae3a0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Positive-QTOF	splash10-05fr-4900000000-90296deba8b4a7fa778d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 10V, Positive-QTOF	splash10-004i-0490000000-0ddff31e344d18cb951d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Positive-QTOF	splash10-000i-0920000000-369f0cf2ba40b21ae3a0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Positive-QTOF	splash10-05fr-4900000000-90296deba8b4a7fa778d	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 10V, Negative-QTOF	splash10-00di-0190000000-0882ee3c4852953c0237	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Negative-QTOF	splash10-0079-1940000000-7dbbd12c62ac4a828608	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Negative-QTOF	splash10-004i-3900000000-fcb880aaba912f0d0b04	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 10V, Negative-QTOF	splash10-00di-0190000000-0882ee3c4852953c0237	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Negative-QTOF	splash10-0079-1940000000-7dbbd12c62ac4a828608	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Negative-QTOF	splash10-004i-3900000000-fcb880aaba912f0d0b04	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 10V, Negative-QTOF	splash10-00di-0090000000-43fb3c0fcbee113584d2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Negative-QTOF	splash10-0abi-0890000000-2cf9487b8eaedea5aa48	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Negative-QTOF	splash10-00dr-2930000000-da8729b97831d3c248f6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 10V, Positive-QTOF	splash10-004i-0090000000-1e032f4d37bafeca5705	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 20V, Positive-QTOF	splash10-000i-0900000000-d5788745c4afc1c8bd5d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Afzelechin 40V, Positive-QTOF	splash10-0a6u-5910000000-e4add39d27430b2d32b6	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

FDB021730

KNApSAcK ID

C00000937

Chemspider ID

248333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Afzelechin

METLIN ID

Not Available

PubChem Compound

282014

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1072001

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Tai BH, Trung TN, Nhiem NX, Ha do T, Van Men C, Duong VB, Van Luong H, Song S, Bae K, Kim YH: A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels of Wisteria floribunda. J Asian Nat Prod Res. 2011 Oct;13(11):1061-8. doi: 10.1080/10286020.2011.603306. Epub 2011 Oct 10. [PubMed:21985227 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. UDP-glucuronosyltransferase 1-1

General function:: Involved in transferase activity, transferring hexosyl groups
Specific function:: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:: UGT1A1
Uniprot ID:: P22309
Molecular weight:: 59590.91

Reactions

Afzelechin → 6-{[3,5-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid	details

Enzyme Details

2. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Afzelechin → [4-(3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic acid	details

Showing metabocard for Afzelechin (HMDB0030823)

MOL for HMDB0030823 (Afzelechin)

3D MOL for HMDB0030823 (Afzelechin)

3D SDF for HMDB0030823 (Afzelechin)

3D-SDF for HMDB0030823 (Afzelechin)

PDB for HMDB0030823 (Afzelechin)

3D PDB for HMDB0030823 (Afzelechin)

SMILES for HMDB0030823 (Afzelechin)

INCHI for HMDB0030823 (Afzelechin)

Structure for HMDB0030823 (Afzelechin)

3D Structure for HMDB0030823 (Afzelechin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions

Reactions