NP-MRD: Showing NP-Card for 6,7-Dihydroxy-4'-methoxyisoflavone (NP0051493)

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Record Information

Version

2.0

Created at

2022-04-27 22:50:18 UTC

Updated at

2022-04-27 22:50:19 UTC

NP-MRD ID

NP0051493

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-Dihydroxy-4'-methoxyisoflavone

Description

6,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one 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, 6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 6,7-Dihydroxy-4'-methoxyisoflavone is found in Baptisia australis, Baptisia leucantha, Myroxylon peruiferum , Platymiscium praecox and Trifolium pratense. 6,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 35  0  0  0  0  0  0  0  0999 V2000
   -6.3608   -0.0764   -0.5743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4862    0.0494    0.5307 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1007    0.1345    0.3583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2443    0.2569    1.4310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8771    0.3414    1.2685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    0.3067    0.0145 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1441    0.3947   -0.1820 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6803    1.2145   -1.1547 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9712    1.2727   -1.3067 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8358    0.5975   -0.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119    0.7034   -0.8041 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0992   -0.0212   -0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4550    0.1261   -0.2926 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6600   -0.8674    0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -1.6028    1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2967   -0.9560    1.1535 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3873   -0.2466    0.4027 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0245   -0.3385    0.5979 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5589   -1.0821    1.4788 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1661    0.1840   -1.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5349    0.0991   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9905   -0.8700   -1.2876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3691   -0.3651   -0.2619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4534    0.8738   -1.1528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7093    0.2837    2.4242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2117    0.4387    2.1388 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023    1.8058   -1.7858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5159    1.3779   -1.5954 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1638   -0.3688    0.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2164   -2.2125    2.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9257   -1.6130    1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088    0.1562   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2055    0.0032   -1.7419 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 20  1  0
 20 21  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 17  2  0
 17 16  1  0
 16 14  2  0
 14 15  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 17 18  1  0
 18 19  2  0
 21  3  1  0
 18  7  1  0
 11 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  5 26  1  0
 20 32  1  0
 21 33  1  0
  8 27  1  0
 16 31  1  0
 15 30  1  0
 13 29  1  0
 11 28  1  0
M  END

  Mrv1652308221906452D          

 21 23  0  0  0  0            999 V2000
    6.4302    4.5375    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
    4.2868    3.3000    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
    5.0013    3.7125    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
    1.4289    0.8250    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
    4.2868    2.4750    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
    2.1434    2.0625    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
    0.7145    2.0625    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    1.2375    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    2.4750    0.0000 O   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
    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
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  2  2  0  0  0  0
  9  3  1  0  0  0  0
 10  4  2  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 12  8  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14  7  2  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 16  2  0  0  0  0
 20  1  1  0  0  0  0
 20 10  1  0  0  0  0
 21  8  1  0  0  0  0
 21 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051493

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=COC2=C(C=C(O)C(O)=C2)C1=O

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

> <INCHI_KEY>
GCWOYVFHJDNKIN-UHFFFAOYSA-N

> <FORMULA>
C16H12O5

> <MOLECULAR_WEIGHT>
284.267

> <EXACT_MASS>
284.068473486

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
28.81919587304147

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.45

> <JCHEM_LOGP>
2.5727664456666663

> <ALOGPS_LOGS>
-3.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.02816812439763

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.5838559528900715

> <JCHEM_PKA_STRONGEST_BASIC>
-4.710406367577148

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
76.1652

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
texasin

> <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      12.003   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336   3.850   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      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   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   4.620   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      12.003   6.930   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    4    9                                                       
CONECT    3    5    9                                                       
CONECT    4    2   10                                                       
CONECT    5    3   10                                                       
CONECT    6   11   13                                                       
CONECT    7   14   15                                                       
CONECT    8   12   21                                                       
CONECT    9    2    3   12                                                  
CONECT   10    4    5   20                                                  
CONECT   11    6   15   16                                                  
CONECT   12    8    9   16                                                  
CONECT   13    6   14   17                                                  
CONECT   14    7   13   18                                                  
CONECT   15    7   11   21                                                  
CONECT   16   11   12   19                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   16                                                            
CONECT   20    1   10                                                       
CONECT   21    8   15                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
6,7-Dihydroxy-3-(4-methoxyphenyl)-4-benzopyrone	Kegg

Chemical Formula

C₁₆H₁₂O₅

Average Mass

284.2670 Da

Monoisotopic Mass

284.06847 Da

IUPAC Name

6,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

texasin

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=COC2=C(C=C(O)C(O)=C2)C1=O

InChI Identifier

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

InChI Key

GCWOYVFHJDNKIN-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
Baptisia australis	Plant	KNApSAcK
Baptisia leucantha	Plant	KNApSAcK
Myroxylon peruiferum	Plant	KNApSAcK
Platymiscium praecox	Plant	KNApSAcK
Trifolium pratense	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
Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Organoheterocyclic compound
Ether
Oxacycle
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methoxyisoflavone (CHEBI:9507 )
isoflavones (C10536 )
Isoflavonoids (C10536 )
Isoflavonoids (LMPK12050101 )

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	3.45	ALOGPS
logP	2.57	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	6.58	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	28.82 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

HMDB0132850

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB089909

KNApSAcK ID

C00002579

Chemspider ID

Not Available

KEGG Compound ID

C10536

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281812

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 6,7-Dihydroxy-4'-methoxyisoflavone (NP0051493)

MOL for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

3D MOL for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

3D SDF for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

3D-SDF for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

PDB for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

3D PDB for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

SMILES for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

INCHI for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

Structure for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)

3D Structure for NP0051493 (6,7-Dihydroxy-4'-methoxyisoflavone)