NP-MRD: Showing NP-Card for 5,7-Dihydroxyisoflavone (NP0045988)

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Record Information

Version

2.0

Created at

2022-03-17 19:46:33 UTC

Updated at

2022-03-17 19:46:33 UTC

NP-MRD ID

NP0045988

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dihydroxyisoflavone

Description

5,7-Dihydroxyisoflavone, also known as acid, mefenaminic or apo mefenamic, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, 5,7-dihydroxyisoflavone is considered to be a flavonoid lipid molecule. 5,7-Dihydroxyisoflavone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5,7-Dihydroxyisoflavone is a bitter tasting compound. Outside of the human body, 5,7-Dihydroxyisoflavone has been detected, but not quantified in, nuts and peanuts. 5,7-Dihydroxyisoflavone is found in Maackia amurensis. This could make 5,7-dihydroxyisoflavone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061305272D          

 19 21  0  0  0  0            999 V2000
    5.7158    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
    5.7158    2.4750    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
    5.0013    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
    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
    0.7145    1.2375    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
    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
    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
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  9  4  2  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17 12  1  0  0  0  0
 18 15  2  0  0  0  0
 19  8  1  0  0  0  0
 19 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045988

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C2C(OC=C(C2=O)C2=CC=CC=C2)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-10-6-12(17)14-13(7-10)19-8-11(15(14)18)9-4-2-1-3-5-9/h1-8,16-17H

> <INCHI_KEY>
PJJGZPJJTHBVMX-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.2375

> <EXACT_MASS>
254.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.54102529278729

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
3.380437711333333

> <ALOGPS_LOGS>
-3.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.288652500802101

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.60820934956541

> <JCHEM_PKA_STRONGEST_BASIC>
-5.1790482621457

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.70200000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.10e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-phenylchromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.669   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      10.669   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   3.850   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       1.334   2.310   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       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    9                                                       
CONECT    5    3    9                                                       
CONECT    6   10   12                                                       
CONECT    7   10   13                                                       
CONECT    8   11   19                                                       
CONECT    9    4    5   11                                                  
CONECT   10    6    7   16                                                  
CONECT   11    8    9   15                                                  
CONECT   12    6   14   17                                                  
CONECT   13    7   14   19                                                  
CONECT   14   12   13   15                                                  
CONECT   15   11   14   18                                                  
CONECT   16   10                                                            
CONECT   17   12                                                            
CONECT   18   15                                                            
CONECT   19    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
2',3'-Dimethyl-2-diphenylaminecarboxylic acid	HMDB
2-((2,3-Dimethylphenyl)amino)-benzoic acid	HMDB
2-((2,3-Dimethylphenyl)amino)benzoic acid	HMDB
2-(2,3-Dimethylanilino)benzoic acid	HMDB
2-(2,3-Dimethylphenyl)amino-benzoic acid	HMDB
2-[(2,3-Dimethylphenyl)amino]-benzoic acid	HMDB
2-[(2,3-Dimethylphenyl)amino]benzoic acid	HMDB
5,7-Dihydroxy-3-phenyl-4H-1-benzopyran-4-one, 9ci	HMDB
Ac. mefenamico	HMDB
Acid, mefenamic	HMDB
Acid, mefenaminic	HMDB
Acido mefenamico	HMDB
Acidum mefenamicum	HMDB
Antigen brand OF mefenamic acid	HMDB
Apo mefenamic	HMDB
Apo-mefenamic	HMDB
Apomefenamic	HMDB
Apotex brand OF mefenamic acid	HMDB
Aps brand OF mefenamic acid	HMDB
Ashbourne brand OF mefenamic acid	HMDB
Bafameritin-m	HMDB
Bafhameritin-m	HMDB
Bonabol	HMDB
Chemidex brand OF mefenamic acid	HMDB
Clonmel brand OF mefenamic acid	HMDB
Contraflam	HMDB
Coslan	HMDB
Dysman	HMDB
Elan brand OF mefenamic acid	HMDB
Farmasierra brand OF mefenamic acid	HMDB
Fenamin	HMDB
First horizon brand OF mefenamic acid	HMDB
Forte, ponstan	HMDB
Lysalgo	HMDB
Mefac	HMDB
Mefacit	HMDB
Mefedolo	HMDB
Mefenamate	HMDB
Mefenamic acid	HMDB
Mefenamic acid (JP15/usp/inn)	HMDB
Mefenaminic acid	HMDB
Mefic	HMDB
Mephenamic acid	HMDB
Mephenaminic acid	HMDB
Methenamic acid	HMDB
Mycasaal	HMDB
N-(2, 3-Dimethylphenyl)anthranilic acid	HMDB
N-(2,3-Dimethylphenyl)anthranilic acid	HMDB
N-(2,3-Xylyl)-2-aminobenzoic acid	HMDB
N-(2,3-Xylyl)-anthranilic acid	HMDB
N-(2,3-Xylyl)anthranilic acid	HMDB
N-2,3-Xylyl-anthranilic acid	HMDB
N-2,3-Xylylanthranilic acid	HMDB
Namphen	HMDB
Nu mefenamic	HMDB
Nu pharm brand OF mefenamic acid	HMDB
Nu-mefenamic	HMDB
Nu-pharm brand OF mefenamic acid	HMDB
Numefenamic	HMDB
Parke davis brand OF mefenamic acid	HMDB
Parkemed	HMDB
Pfizer brand OF mefenamic acid	HMDB
Pharmascience brand OF mefenamic acid	HMDB
Pinalgesic	HMDB
Pinewood brand OF mefenamic acid	HMDB
PMS Mefenamic acid	HMDB
PMS-Mefenamic acid	HMDB
Ponalar	HMDB
Ponalgic	HMDB
Ponmel	HMDB
Ponstan	HMDB
Ponstan forte	HMDB
Ponstel	HMDB
Ponstil	HMDB
Ponstyl	HMDB
Ponsyl	HMDB
Pontal	HMDB
Rolan	HMDB
Rowa brand OF mefenamic acid	HMDB
Tamany bonsan	HMDB
Tanston	HMDB
Vialidon	HMDB
Warner lambert brand OF mefenamic acid	HMDB
Warner-lambert brand OF mefenamic acid	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Mass

254.2375 Da

Monoisotopic Mass

254.05791 Da

IUPAC Name

5,7-dihydroxy-3-phenyl-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-3-phenylchromen-4-one

CAS Registry Number

4044-00-2

SMILES

OC1=CC(O)=C2C(OC=C(C2=O)C2=CC=CC=C2)=C1

InChI Identifier

InChI=1S/C15H10O4/c16-10-6-12(17)14-13(7-10)19-8-11(15(14)18)9-4-2-1-3-5-9/h1-8,16-17H

InChI Key

PJJGZPJJTHBVMX-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
Arachis hypogaea	FooDB	KNAPSACK
Maackia amurensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents

Substituents

Hydroxyisoflavonoid
Isoflavone
Chromone
Benzopyran
1-benzopyran
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050160 )

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	3.43	ALOGPS
logP	3.38	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.54 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