NP-MRD: Showing NP-Card for 5,7-Dihydroxy-4-Methylisoflavone (NP0331684)

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Record Information

Version

2.0

Created at

2023-06-09 20:02:35 UTC

Updated at

2024-09-03 04:16:30 UTC

NP-MRD ID

NP0331684

Natural Product DOI

https://doi.org/10.57994/0688

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dihydroxy-4-Methylisoflavone

Description

Biochanin A, also known as olmelin or pratensol, 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. Thus, biochanin a is considered to be a flavonoid lipid molecule. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside). The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. Biochanin A is an O-methylated isoflavone. Biochanin A is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Biochanin A is found, on average, in the highest concentration within a few different foods, such as milk (cow), peanuts, and soy beans and in a lower concentration in beers. Biochanin A has also been detected, but not quantified in, several different foods, such as lingonberries, savoy cabbages, garlics, garden rhubarbs, and red rices. This could make biochanin a a potential biomarker for the consumption of these foods. Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A is a potentially toxic compound. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro. 5,7-Dihydroxy-4-Methylisoflavone was first documented in 2006 (PMID: 16903077). Biochanin A can be found in red clover in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes (PMID: 18565930) (PMID: 16651441) (PMID: 16598420).

Structure

MOL SDF PDB SMILES InChI

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>
NP0331684

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

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
5,7-Dihydroxy-4'-methoxy-isoflavone	HMDB
5,7-Dihydroxy-4'-methoxy-isoflavone (8ci)	HMDB
Biochanin	HMDB
Biochanine a	HMDB
Genistein 4-methyl ether	HMDB
Biochanin a, 14C-labeled	HMDB

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

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

Traditional Name

biochanin

CAS Registry Number

Not Available

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	ztmnb@umsystem.edu	Not Available	Not Available	2024-05-11	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	ztmnb@umsystem.edu	Sumner lab, University of Missouri	Zach Tretter	2024-05-11	View Spectrum

Species

Species of Origin

Not Available

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 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0002338

DrugBank ID

Not Available

Phenol Explorer Compound ID

FoodDB 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

Good Scents ID

Not Available

References

General References

Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. [PubMed:18565930 ]
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. doi: 10.1007/BF02969267. [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. doi: 10.1158/0008-5472.CAN-05-2957. [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. doi: 10.1007/s11060-006-9126-0. Epub 2006 Apr 6. [PubMed:16598420 ]

Showing NP-Card for 5,7-Dihydroxy-4-Methylisoflavone (NP0331684)

MOL for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

3D MOL for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

3D SDF for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

3D-SDF for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

PDB for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

3D PDB for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

SMILES for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

INCHI for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

Structure for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)

3D Structure for NP0331684 (5,7-Dihydroxy-4-Methylisoflavone)