NP-MRD: Showing NP-Card for 2'-Hydroxy-5'-methoxybiochanin A (NP0056868)

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Record Information

Version

2.0

Created at

2022-04-28 02:29:39 UTC

Updated at

2022-04-28 02:29:39 UTC

NP-MRD ID

NP0056868

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxy-5'-methoxybiochanin A

Description

2'-Hydroxy-5'-methoxybiochanin a 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, 2'-hydroxy-5'-methoxybiochanin a is considered to be a flavonoid lipid molecule. 2'-Hydroxy-5'-methoxybiochanin A is found in Erythrina eriotriocha and Erythrina sigmoidea. 2'-Hydroxy-5'-methoxybiochanin a is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 40  0  0  0  0  0  0  0  0999 V2000
   -5.5568   -1.7045    1.0707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8957   -0.4787    0.8553 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5495   -0.4191    0.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7586   -1.5222    0.3786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4209   -1.4540    0.0491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6899   -2.6481   -0.0765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8601   -0.2109   -0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5486   -0.0927   -0.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349    0.2028   -1.7636 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2016    0.3038   -2.0294 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1497    0.1378   -1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4501    0.2749   -1.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4706    0.1057   -0.6320 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8082    0.2425   -1.0472 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1303   -0.1912    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7967   -0.3331    1.0972 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022   -0.6290    2.4067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8032   -0.1648    0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -0.2844    0.5271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1066   -0.5577    1.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6590    0.9029    0.0029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9959    0.8339    0.3328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8177    1.9318    0.4863 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2779    3.2190    0.2989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4564   -2.3089    0.1662 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6264   -1.4624    1.3082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0690   -2.1949    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2294   -2.4903    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2919   -2.6316   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891    0.3519   -2.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6828    0.5102   -2.5806 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1979    1.1820   -0.9794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9426   -0.3207    1.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8341   -0.7804    2.9773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2599    1.9176   -0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2978    3.3439    0.7982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9700    3.9077    0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2251    3.5113   -0.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 19 20  2  0
 22  3  1  0
 19  8  1  0
 18 11  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  4 28  1  0
  6 29  1  0
 21 35  1  0
 24 36  1  0
 24 37  1  0
 24 38  1  0
  9 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
M  END

  Mrv1533004241502362D          

 24 26  0  0  0  0            999 V2000
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 O   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
   -1.4289   -1.6500    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    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
    3.5724   -0.4125    0.0000 C   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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -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  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  7 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
 15 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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0056868

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C=C1OC)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C17H14O7/c1-22-13-5-9(11(19)6-14(13)23-2)10-7-24-15-4-8(18)3-12(20)16(15)17(10)21/h3-7,18-20H,1-2H3

> <INCHI_KEY>
XTQFIPOLABHASM-UHFFFAOYSA-N

> <FORMULA>
C17H14O7

> <MOLECULAR_WEIGHT>
330.292

> <EXACT_MASS>
330.073952791

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
32.49199221258577

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
2.761529858333333

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.093422564716448

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5409194700532804

> <JCHEM_PKA_STRONGEST_BASIC>
-4.524746132807627

> <JCHEM_POLAR_SURFACE_AREA>
105.45000000000002

> <JCHEM_REFRACTIVITY>
84.60929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-(2-hydroxy-4,5-dimethoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.667   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    7   13   23                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   15   23                                                  
CONECT   23   22   12   24                                                  
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
2'-HMBA	MeSH

Chemical Formula

C₁₇H₁₄O₇

Average Mass

330.2920 Da

Monoisotopic Mass

330.07395 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C=C1OC)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C17H14O7/c1-22-13-5-9(11(19)6-14(13)23-2)10-7-24-15-4-8(18)3-12(20)16(15)17(10)21/h3-7,18-20H,1-2H3

InChI Key

XTQFIPOLABHASM-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
Erythrina eriotriocha	Plant	KNApSAcK
Erythrina sigmoidea	LOTUS Database	35616633

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
3p-methoxyisoflavone
Isoflavone
Hydroxyisoflavonoid
Chromone
Methoxyphenol
1-benzopyran
Benzopyran
Dimethoxybenzene
O-dimethoxybenzene
4-alkoxyphenol
Methoxybenzene
Phenol ether
Phenoxy compound
Anisole
Pyranone
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Ether
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050334 )

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	3.01	ALOGPS
logP	2.76	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	105.45 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.61 m³·mol⁻¹	ChemAxon
Polarizability	32.49 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5492434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2'-Hydroxy-5'-methoxybiochanin A (NP0056868)

MOL for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

3D MOL for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

3D SDF for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

3D-SDF for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

PDB for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

3D PDB for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

SMILES for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

INCHI for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

Structure for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)

3D Structure for NP0056868 (2'-Hydroxy-5'-methoxybiochanin A)