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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2022-03-07 02:49:14 UTC

HMDB ID

HMDB0002338

Secondary Accession Numbers

HMDB02338

Metabolite Identification

Common Name

Biochanin A

Description

The phytoestrogen biochanin A is an isoflavone derivative isolated from red clover Trifolium pratense with anticarcinogenic properties. Treating MCF-7 human breast carcinoma cells with biochanin A alone caused the accumulation of CYP1A1 mRNA and an increase in CYP1A1-specific 7-ethoxyresorufin O-deethylase (EROD) activity in a dose dependent manner. Biochanin A may be a natural ligand to bind on aryl hydrocarbon receptor acting as an antagonist/agonist of the pathway. (PMID: 16903077 ). Biochanin A suppress nuclear factor-kappaB-driven interleukin-6 (IL6) expression. In addition to its physiologic immune function as an acute stress cytokine, sustained elevated expression levels of IL6 promote chronic inflammatory disorders, aging frailty, and tumorigenesis. (PMID: 16651441 ). Biochanin A induces a decrease in invasive activity of U87MG cells in a dose-related manner. (PMID: 16598420 ). Biochanin A activates peroxisome proliferator-activated receptors (PPAR) PPARalpha, PPARgamma, and adipocyte differentiation in vitro of 3T3-L1 preadipocytes, suggesting potential value of isoflavones, especially biochanin A and their parent botanicals, as antidiabetic agents and for use in regulating lipid metabolism. (PMID: 16549448 ).

Structure

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

HMDB0002338
     RDKit          3D
Biochanin A
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0993    0.4712   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884   -0.1155    0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0056   -0.0236    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2472    0.6353   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    0.7046   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    0.1180    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    0.1810    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311    0.4779    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    0.5367    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3003    1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899    0.3656    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    0.1244    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5246    0.1851    0.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842   -0.1801   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2221   -0.2449   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.5536   -2.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -0.0041   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -0.0738   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021   -0.3513   -1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.5317    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3668   -0.6055    1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9501   -0.1607   -1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954    1.5017   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1841    0.5139   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.0868   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    1.2334   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.6694    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7171    0.6062    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0873   -0.0006   -0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356   -0.3757   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.7416   -3.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -1.0199    2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -1.1147    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 20 32  1  0
 21 33  1  0
M  END

Biochanin A
  Mrv1572001071617322D          

 21 23  0  0  0  0            999 V2000
    4.1848   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4703   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4703   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0414   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7559   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3269   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2454    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5310   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8165   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6125   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  9 20  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002338

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3

> <INCHI_KEY>
WUADCCWRTIWANL-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.681815372351288

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.44

> <JCHEM_LOGP>
3.2227664456666663

> <ALOGPS_LOGS>
-3.69

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.149242145390627

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5479486099736

> <JCHEM_PKA_STRONGEST_BASIC>
-4.716057035165476

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.83e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
biochanin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002338
     RDKit          3D
Biochanin A
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0993    0.4712   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884   -0.1155    0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0056   -0.0236    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2472    0.6353   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    0.7046   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    0.1180    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    0.1810    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311    0.4779    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    0.5367    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3003    1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899    0.3656    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    0.1244    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5246    0.1851    0.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842   -0.1801   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2221   -0.2449   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.5536   -2.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -0.0041   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -0.0738   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021   -0.3513   -1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.5317    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3668   -0.6055    1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9501   -0.1607   -1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954    1.5017   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1841    0.5139   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.0868   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    1.2334   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.6694    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7171    0.6062    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0873   -0.0006   -0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356   -0.3757   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.7416   -3.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -1.0199    2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -1.1147    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 20 32  1  0
 21 33  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Biochanin A                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       7.812  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.812  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.478  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.478  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.144  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.811  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.811  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.144  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.477  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.477  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.143   0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.190  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.524   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.858  -0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.191   0.000   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.858  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.524  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.524  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.190  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.143  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.143  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19    9   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0002338
HETATM    1  C1  UNL     1       6.099   0.471  -0.862  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.388  -0.116   0.229  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.006  -0.024   0.323  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.247   0.635  -0.626  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.873   0.705  -0.497  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.241   0.118   0.580  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.202   0.181   0.733  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.831   0.478   1.915  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.116   0.537   2.062  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.917   0.300   1.023  1.00  0.00           C  
HETATM   11  C9  UNL     1      -4.290   0.366   1.191  1.00  0.00           C  
HETATM   12  C10 UNL     1      -5.134   0.124   0.128  1.00  0.00           C  
HETATM   13  O3  UNL     1      -6.525   0.185   0.275  1.00  0.00           O  
HETATM   14  C11 UNL     1      -4.584  -0.180  -1.091  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.222  -0.245  -1.258  1.00  0.00           C  
HETATM   16  O4  UNL     1      -2.631  -0.554  -2.492  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.352  -0.004  -0.195  1.00  0.00           C  
HETATM   18  C14 UNL     1      -0.976  -0.074  -0.380  1.00  0.00           C  
HETATM   19  O5  UNL     1      -0.502  -0.351  -1.494  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.007  -0.532   1.513  1.00  0.00           C  
HETATM   21  C16 UNL     1       3.367  -0.606   1.393  1.00  0.00           C  
HETATM   22  H1  UNL     1       5.950  -0.161  -1.752  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.695   1.502  -0.992  1.00  0.00           H  
HETATM   24  H3  UNL     1       7.184   0.514  -0.634  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.755   1.087  -1.459  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.283   1.233  -1.262  1.00  0.00           H  
HETATM   27  H6  UNL     1      -0.156   0.669   2.758  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.717   0.606   2.155  1.00  0.00           H  
HETATM   29  H8  UNL     1      -7.087  -0.001  -0.536  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.236  -0.376  -1.950  1.00  0.00           H  
HETATM   31  H10 UNL     1      -3.182  -0.742  -3.311  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.578  -1.020   2.392  1.00  0.00           H  
HETATM   33  H12 UNL     1       3.986  -1.115   2.121  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    6   26
CONECT    6    7   20
CONECT    7    8    8   18
CONECT    8    9   27
CONECT    9   10
CONECT   10   11   11   17
CONECT   11   12   28
CONECT   12   13   14   14
CONECT   13   29
CONECT   14   15   30
CONECT   15   16   17   17
CONECT   16   31
CONECT   17   18
CONECT   18   19   19
CONECT   20   21   21   32
CONECT   21   33
END

HMDB0002338
     RDKit          3D
Biochanin A
 33 35  0  0  0  0  0  0  0  0999 V2000
    6.0993    0.4712   -0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3884   -0.1155    0.2286 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0056   -0.0236    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2472    0.6353   -0.6264 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8732    0.7046   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2412    0.1180    0.5803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2021    0.1810    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8311    0.4779    1.9149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1164    0.5367    2.0619 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9170    0.3003    1.0232 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2899    0.3656    1.1905 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1341    0.1244    0.1282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5246    0.1851    0.2754 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5842   -0.1801   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2221   -0.2449   -1.2575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6313   -0.5536   -2.4915 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523   -0.0041   -0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9760   -0.0738   -0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021   -0.3513   -1.4938 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -0.5317    1.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3668   -0.6055    1.3933 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9501   -0.1607   -1.7525 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6954    1.5017   -0.9925 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1841    0.5139   -0.6336 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7549    1.0868   -1.4594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2828    1.2334   -1.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.6694    2.7584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7171    0.6062    2.1547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0873   -0.0006   -0.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2356   -0.3757   -1.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1817   -0.7416   -3.3113 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5776   -1.0199    2.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9860   -1.1147    2.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  2  0
  6 20  1  0
 20 21  2  0
 21  3  1  0
 18  7  1  0
 17 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 14 30  1  0
 16 31  1  0
 20 32  1  0
 21 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4'-Methylgenistein	ChEBI
5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one	ChEBI
5,7-Dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one	ChEBI
5,7-Dihydroxy-4'-methoxyisoflavone	ChEBI
Olmelin	ChEBI
Pratensol	ChEBI
Biochanin a, 14C-labeled	MeSH
Genistein 4-methyl ether	MeSH
5,7-Dihydroxy-4'-methoxy-isoflavone	HMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)	HMDB
Biochanin	HMDB
Biochanine a	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Molecular Weight

284.267

Monoisotopic Molecular Weight

284.068473486

IUPAC Name

5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

biochanin

CAS Registry Number

491-80-5

SMILES

COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3

InChI Key

WUADCCWRTIWANL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4'-o-methylisoflavones. These are isoflavones with methoxy groups attached to the C4' atom of the isoflavone backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

O-methylated isoflavonoids

Direct Parent

4'-O-methylisoflavones

Alternative Parents

Substituents

4p-o-methylisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Pyran
Vinylogous acid
Heteroaromatic compound
Ether
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:17574 )
7-hydroxyisoflavones (CHEBI:17574 )
isoflavones (C00814 )
Isoflavonoids (C00814 )
Isoflavonoids (LMPK12050229 )

Ontology

Not Available

Exogenous (HMDB: HMDB0002338)

Food

Soy

Soy bean (FooDB: FOOD00085)

Pulse

Pulses (FooDB: FOOD00867)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	518.57 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	71.1 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.341 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	170.411	30932474
[M-H]-	Not Available	170.411	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001933

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.058 g/L	ALOGPS
logP	3.44	ALOGPS
logP	3.22	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.55	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.17 m³·mol⁻¹	ChemAxon
Polarizability	28.68 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
DeepCCS	[M+H]+	166.538	30932474
DeepCCS	[M-H]-	164.18	30932474
DeepCCS	[M-2H]-	197.067	30932474
DeepCCS	[M+Na]+	172.632	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	161.3	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.6	32859911
AllCCS	[M-H]-	166.8	32859911
AllCCS	[M+Na-2H]-	166.1	32859911
AllCCS	[M+HCOO]-	165.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Biochanin A	COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	4237.2	Standard polar	33892256
Biochanin A	COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	2845.9	Standard non polar	33892256
Biochanin A	COC1=CC=C(C=C1)C1=COC2=CC(O)=CC(O)=C2C1=O	2933.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Biochanin A,1TMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O)=C3C2=O)C=C1	3116.6	Semi standard non polar	33892256
Biochanin A,1TMS,isomer #2	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	3057.8	Semi standard non polar	33892256
Biochanin A,2TMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3C2=O)C=C1	3002.5	Semi standard non polar	33892256
Biochanin A,1TBDMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O)=C3C2=O)C=C1	3359.1	Semi standard non polar	33892256
Biochanin A,1TBDMS,isomer #2	COC1=CC=C(C2=COC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3303.7	Semi standard non polar	33892256
Biochanin A,2TBDMS,isomer #1	COC1=CC=C(C2=COC3=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1	3489.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Biochanin A GC-MS (2 TMS)	splash10-03di-2944800000-78e1196ce4a6b5cc510e	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Biochanin A GC-MS (Non-derivatized)	splash10-03di-2944800000-78e1196ce4a6b5cc510e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Biochanin A GC-EI-TOF (Non-derivatized)	splash10-03di-1833900000-f09d96dccb297f00dcd5	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biochanin A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0490000000-c605105233a09c99c287	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biochanin A GC-MS (2 TMS) - 70eV, Positive	splash10-03k9-3439600000-64fa3b3cc333606e4699	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Biochanin A 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 40V, Negative-QTOF	splash10-014r-0190000000-7f6a864949fd18a14e8b	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 50V, Negative-QTOF	splash10-03yr-0790000000-5a2ccc494db05b9e19e7	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-1469c7dc6efca44dce49	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF , Negative-QTOF	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 20V, Negative-QTOF	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-08-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 40V, Negative-QTOF	splash10-014r-0190000000-7f6a864949fd18a14e8b	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 50V, Negative-QTOF	splash10-03yr-0790000000-5a2ccc494db05b9e19e7	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 30V, Negative-QTOF	splash10-014i-0090000000-1469c7dc6efca44dce49	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF , Negative-QTOF	splash10-001i-0090000000-ab7e811e30dd92aa8de3	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A ESI-TOF 20V, Negative-QTOF	splash10-0159-0090000000-48950d676f0cb98a7321	2017-09-12	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Positive-QTOF	splash10-0w9c-0490000000-9f316916713e817996ee	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Positive-QTOF	splash10-0a4i-0019000000-09139525e32bfa06cffd	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Biochanin A DI-ESI-qTof , Negative-QTOF	splash10-014i-0190000000-3d2d9ae76aea2ba8e0d4	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 10V, Positive-QTOF	splash10-000i-0090000000-47e7f5888047896fbeab	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 20V, Positive-QTOF	splash10-000i-0090000000-0d44debd7dc24705b82a	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 40V, Positive-QTOF	splash10-0udi-4970000000-62cdcc296c60a0b9a572	2015-05-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 10V, Positive-QTOF	splash10-000i-0090000000-47e7f5888047896fbeab	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 20V, Positive-QTOF	splash10-000i-0090000000-0d44debd7dc24705b82a	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 40V, Positive-QTOF	splash10-0udi-4970000000-62cdcc296c60a0b9a572	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 10V, Negative-QTOF	splash10-001i-0090000000-57c90dbeeae680583b28	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 20V, Negative-QTOF	splash10-001i-0090000000-cfc655e2b327c5f14670	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 40V, Negative-QTOF	splash10-0ue9-3890000000-4aefff84d287041c16e9	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 10V, Negative-QTOF	splash10-001i-0090000000-57c90dbeeae680583b28	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 20V, Negative-QTOF	splash10-001i-0090000000-cfc655e2b327c5f14670	2015-05-27	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Biochanin A 40V, Negative-QTOF	splash10-0ue9-3890000000-4aefff84d287041c16e9	2015-05-27	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Detected and Quantified	0.0088 (0.0027-0.0200) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 397	15506819	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Consuming polyphenols described by Phenol-Explorer entry 397	20067656	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

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

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Biochanin_A

METLIN ID

Not Available

PubChem Compound

5280373

PDB ID

Not Available

ChEBI ID

17574

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1223481

References

Synthesis Reference

Gakhokidze, A. M. Synthesis of olmelin. Zhurnal Prikladnoi Khimii (Sankt-Peterburg, Russian Federation) (1950), 23 559-60.

Material Safety Data Sheet (MSDS)

Not Available

General References

Han EH, Kim JY, Jeong HG: Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Arch Pharm Res. 2006 Jul;29(7):570-6. [PubMed:16903077 ]
Vanden Berghe W, Dijsselbloem N, Vermeulen L, Ndlovu MN, Boone E, Haegeman G: Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity. Cancer Res. 2006 May 1;66(9):4852-62. [PubMed:16651441 ]
Puli S, Lai JC, Bhushan A: Inhibition of matrix degrading enzymes and invasion in human glioblastoma (U87MG) cells by isoflavones. J Neurooncol. 2006 Sep;79(2):135-42. Epub 2006 Apr 6. [PubMed:16598420 ]
Shen P, Liu MH, Ng TY, Chan YH, Yong EL: Differential effects of isoflavones, from Astragalus membranaceus and Pueraria thomsonii, on the activation of PPARalpha, PPARgamma, and adipocyte differentiation in vitro. J Nutr. 2006 Apr;136(4):899-905. [PubMed:16549448 ]

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

Biochanin A → 3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic acid	details

Showing metabocard for Biochanin A (HMDB0002338)

MOL for HMDB0002338 (Biochanin A)

3D MOL for HMDB0002338 (Biochanin A)

3D SDF for HMDB0002338 (Biochanin A)

3D-SDF for HMDB0002338 (Biochanin A)

PDB for HMDB0002338 (Biochanin A)

3D PDB for HMDB0002338 (Biochanin A)

SMILES for HMDB0002338 (Biochanin A)

INCHI for HMDB0002338 (Biochanin A)

Structure for HMDB0002338 (Biochanin A)

3D Structure for HMDB0002338 (Biochanin A)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions