NP-MRD: Showing NP-Card for 2'-Hydroxybiochanin A (NP0056550)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 02:17:31 UTC

Updated at

2022-04-28 02:17:31 UTC

NP-MRD ID

NP0056550

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxybiochanin A

Description

5,7-Dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one, also known as dehydroferreirin or 5,7,2'-trihydroxy-4'-methoxyisoflavone, 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, 5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. A methoxyisoflavone in which the methoxy group is located at position 4' together with three additional hydroxy substituents at positions 2' 5 and 7. 5,7-Dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2'-Hydroxybiochanin A is found in Astragalus adsurgens, Dalbergia parviflora, Euchresta formosana, Ficus nymphaeifolia , Haplormosia monophylla, Oxytropis falcata, Virola caducifolia, Virola cadudifolia and Virola multinervia. 2'-Hydroxybiochanin A was first documented in 2011 (PMID: 21495101). 5,7-Dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one exists in all living organisms, ranging from bacteria to humans.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 36  0  0  0  0  0  0  0  0999 V2000
   -6.1225   -0.3943    0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1950   -0.5736   -0.8641 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8587   -0.3020   -0.6593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9518   -0.5052   -1.6892 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6089   -0.2428   -1.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1422    0.2224   -0.2693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2987    0.4876   -0.0830 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7989    1.6960    0.3260 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847    1.9193    0.4464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9657    0.9924    0.1816 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3001    1.2629    0.3176 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    0.2704    0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5706    0.5178    0.1637 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8113   -0.9598   -0.3735 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4602   -1.2647   -0.5222 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1233   -2.5209   -0.9315 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5448   -0.2779   -0.2427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2057   -0.5261   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7501   -1.6154   -0.7429 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514    0.4216    0.7362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5896    0.8940    1.9683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4171    0.1607    0.5499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0527   -0.9372   -0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2780    0.6732    0.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7261   -0.8647    1.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2866   -0.8602   -2.6580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337   -0.4074   -2.3049 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0493    2.4744    0.5474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6540    2.2486    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9416    1.4067    0.4564 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5176   -1.7472   -0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3188   -3.0107   -1.1086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2632    1.0415    2.7109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1133    0.3206    1.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 22  2  0
 22 20  1  0
 20 21  1  0
 20  6  2  0
  6  5  1  0
  5  4  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
  4  3  1  0
 18  7  1  0
 17 10  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 22 34  1  0
 21 33  1  0
  5 27  1  0
  4 26  1  0
  8 28  1  0
 11 29  1  0
 13 30  1  0
 14 31  1  0
 16 32  1  0
M  END


  Mrv1652308221919282D          

 22 24  0  0  0  0            999 V2000
    7.1447    3.3000    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
    4.2868    3.3000    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
    1.4289    0.8250    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
    3.5724    1.2375    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
    5.7158    3.3000    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    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
    2.1434    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
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    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
    6.4302    3.7125    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
  3  2  2  0  0  0  0
  8  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11  7  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  2  0  0  0  0
 13  4  1  0  0  0  0
 14  5  2  0  0  0  0
 15 13  2  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 15  1  0  0  0  0
 17  8  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 16  2  0  0  0  0
 21  1  1  0  0  0  0
 21  9  1  0  0  0  0
 22  7  1  0  0  0  0
 22 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056550

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-7,17-19H,1H3

> <INCHI_KEY>
OZEVXMDBOINMTC-UHFFFAOYSA-N

> <FORMULA>
C16H12O6

> <MOLECULAR_WEIGHT>
300.266

> <EXACT_MASS>
300.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.566796812358945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

> <JCHEM_LOGP>
2.9192011239999993

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.012002601760113

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.538724920984323

> <JCHEM_PKA_STRONGEST_BASIC>
-4.723626930085797

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
78.1461

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2'-hydroxybiochanin A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0      13.337   6.160   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       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   4.620   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       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   2.310   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      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2    3    9                                                       
CONECT    3    2   10                                                       
CONECT    4    8   13                                                       
CONECT    5    8   14                                                       
CONECT    6    9   12                                                       
CONECT    7   11   22                                                       
CONECT    8    4    5   17                                                  
CONECT    9    2    6   21                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   16                                                  
CONECT   12    6   10   18                                                  
CONECT   13    4   15   19                                                  
CONECT   14    5   15   22                                                  
CONECT   15   13   14   16                                                  
CONECT   16   11   15   20                                                  
CONECT   17    8                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   16                                                            
CONECT   21    1    9                                                       
CONECT   22    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Value	Source
5,7,2'-Trihydroxy-4'-methoxyisoflavone	ChEBI
Dehydroferreirin	ChEBI

Chemical Formula

C₁₆H₁₂O₆

Average Mass

300.2660 Da

Monoisotopic Mass

300.06339 Da

IUPAC Name

5,7-dihydroxy-3-(2-hydroxy-4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

2'-hydroxybiochanin A

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H12O6/c1-21-9-2-3-10(12(18)6-9)11-7-22-14-5-8(17)4-13(19)15(14)16(11)20/h2-7,17-19H,1H3

InChI Key

OZEVXMDBOINMTC-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Astragalus adsurgens	LOTUS Database	35616633
Dalbergia parviflora	LOTUS Database	35616633
Euchresta formosana	LOTUS Database	35616633
Ficus nymphaeifolia	Plant	KNApSAcK
Haplormosia monophylla	Plant	KNApSAcK
Oxytropis falcata	LOTUS Database	35616633
Virola caducifolia	Plant	KNApSAcK
Virola cadudifolia	Plant	KNApSAcK
Virola multinervia	Plant	KNApSAcK

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:31064 )
7-hydroxyisoflavones (CHEBI:31064 )
2'-hydroxyisoflavones (CHEBI:31064 )
isoflavones (C12135 )
Isoflavonoids (C12135 )
Isoflavonoids (LMPK12050328 )

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	2.92	ChemAxon
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	78.15 m³·mol⁻¹	ChemAxon
Polarizability	29.57 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

HMDB0134009

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB091030

KNApSAcK ID

C00009457

Chemspider ID

Not Available

KEGG Compound ID

C12135

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282075

PDB ID

Not Available

ChEBI ID

31064

Good Scents ID

Not Available

References

General References

Mansoor TA, Ramalho RM, Luo X, Ramalhete C, Rodrigues CM, Ferreira MJ: Isoflavones as apoptosis inducers in human hepatoma HuH-7 cells. Phytother Res. 2011 Dec;25(12):1819-24. doi: 10.1002/ptr.3498. Epub 2011 Apr 14. [PubMed:21495101 ]

Showing NP-Card for 2'-Hydroxybiochanin A (NP0056550)

MOL for NP0056550 (2'-Hydroxybiochanin A)

3D MOL for NP0056550 (2'-Hydroxybiochanin A)

3D SDF for NP0056550 (2'-Hydroxybiochanin A)

3D-SDF for NP0056550 (2'-Hydroxybiochanin A)

PDB for NP0056550 (2'-Hydroxybiochanin A)

3D PDB for NP0056550 (2'-Hydroxybiochanin A)

SMILES for NP0056550 (2'-Hydroxybiochanin A)

INCHI for NP0056550 (2'-Hydroxybiochanin A)

Structure for NP0056550 (2'-Hydroxybiochanin A)

3D Structure for NP0056550 (2'-Hydroxybiochanin A)