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Showing NP-Card for 7-hydroxyisoflavone (NP0210534)

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Record Information
Version2.0
Created at2022-09-05 08:23:35 UTC
Updated at2022-09-05 08:23:35 UTC
NP-MRD IDNP0210534
Secondary Accession NumbersNone
Natural Product Identification
Common Name7-hydroxyisoflavone
Description7-Hydroxy-3-phenyl-4H-chromen-4-one 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. 7-hydroxyisoflavone is found in Muntingia calabura. 7-hydroxyisoflavone was first documented in 1986 (PMID: 22175340). 7-Hydroxy-3-phenyl-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 16864424) (PMID: 21562980).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0210534 (7-hydroxyisoflavone)


  Mrv1652308221900042D          

 18 20  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    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
    0.7145    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
    3.5724    2.0625    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    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
    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
  7  6  2  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
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18  9  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
Download

3D MOL for NP0210534 (7-hydroxyisoflavone)

     RDKit          3D

 28 30  0  0  0  0  0  0  0  0999 V2000
    0.1609   -1.8595    0.0485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2542   -0.6792    0.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    0.3863   -0.0540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0616    0.1957   -0.0789 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8655    0.8856   -0.9527 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2322    0.6719   -0.9415 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.2295   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9960   -0.9292    0.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6360   -0.6964    0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0723    1.6494   -0.0931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2349    1.8374   -0.0710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0781    0.8426   -0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4451    1.0349    0.0121 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3539   -0.0008    0.0752 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7180    0.3040    0.0938 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8914   -1.3018    0.1179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5261   -1.5226    0.0959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6305   -0.4759    0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4525    1.6117   -1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8605    1.2286   -1.6433 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8718   -0.3841   -0.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4429   -1.6448    1.5255 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0375   -1.2688    1.5058 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    2.4985   -0.1431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8322    2.0424   -0.0203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1293    0.4377    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6127   -2.1221    0.1679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1377   -2.5119    0.1275 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 18  2  0
 18 17  1  0
 17 16  2  0
 18  2  1  0
  2  1  2  0
  2  3  1  0
  3 10  2  0
 10 11  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
 16 14  1  0
  9  4  1  0
 11 12  1  0
 15 26  1  0
 13 25  1  0
 17 28  1  0
 16 27  1  0
 10 24  1  0
  5 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
M  END
Download

3D SDF for NP0210534 (7-hydroxyisoflavone)


  Mrv1652308221900042D          

 18 20  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    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
    0.7145    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
    3.5724    2.0625    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    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
    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
  7  6  2  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
 11  8  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 12  2  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 15  2  0  0  0  0
 18  9  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O3/c16-11-6-7-12-14(8-11)18-9-13(15(12)17)10-4-2-1-3-5-10/h1-9,16H

> <INCHI_KEY>
WMKOZARWBMFKAS-UHFFFAOYSA-N

> <FORMULA>
C15H10O3

> <MOLECULAR_WEIGHT>
238.242

> <EXACT_MASS>
238.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
24.704213702640207

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-3-phenyl-4H-chromen-4-one

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
3.034003033

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.478089131341357

> <JCHEM_PKA_STRONGEST_BASIC>
-5.336141541729694

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
67.7211

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.03e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxyisoflavone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0210534 (7-hydroxyisoflavone)

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PDB for NP0210534 (7-hydroxyisoflavone)
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      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   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   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       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   3.850   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       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       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   18  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   10                                                       
CONECT    5    3   10                                                       
CONECT    6    7   11                                                       
CONECT    7    6   12                                                       
CONECT    8   11   14                                                       
CONECT    9   13   18                                                       
CONECT   10    4    5   13                                                  
CONECT   11    6    8   16                                                  
CONECT   12    7   14   15                                                  
CONECT   13    9   10   15                                                  
CONECT   14    8   12   18                                                  
CONECT   15   12   13   17                                                  
CONECT   16   11                                                            
CONECT   17   15                                                            
CONECT   18    9   14                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

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3D PDB for NP0210534 (7-hydroxyisoflavone)
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SMILES for NP0210534 (7-hydroxyisoflavone)
OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC=CC=C1
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INCHI for NP0210534 (7-hydroxyisoflavone)
InChI=1S/C15H10O3/c16-11-6-7-12-14(8-11)18-9-13(15(12)17)10-4-2-1-3-5-10/h1-9,16H
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View in JSmol
SynonymsNot Available
Chemical FormulaC15H10O3
Average Mass238.2420 Da
Monoisotopic Mass238.06299 Da
IUPAC Name7-hydroxy-3-phenyl-4H-chromen-4-one
Traditional Name7-hydroxyisoflavone
CAS Registry NumberNot Available
SMILES
OC1=CC2=C(C=C1)C(=O)C(=CO2)C1=CC=CC=C1
InChI Identifier
InChI=1S/C15H10O3/c16-11-6-7-12-14(8-11)18-9-13(15(12)17)10-4-2-1-3-5-10/h1-9,16H
InChI KeyWMKOZARWBMFKAS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Muntingia calaburaLOTUS Database
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassIsoflavonoids  
Sub ClassIsoflav-2-enes  
Direct ParentIsoflavones  
Alternative Parents
Substituents
  • Hydroxyisoflavonoid
    • 

  • Isoflavone
    • 

  • Chromone
    • 

  • Benzopyran
    • 

  • 1-benzopyran
    • 

  • 1-hydroxy-2-unsubstituted benzenoid
    • 

  • Pyranone
    • 

  • Monocyclic benzene moiety
    • 

  • Pyran
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Oxacycle
    • 

  • Organoheterocyclic compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.64ALOGPS
logP3.03ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)6.48ChemAxon
pKa (Strongest Basic)-5.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.72 m³·mol⁻¹ChemAxon
Polarizability24.7 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0130492  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB089305  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC15615  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5376891  
PDB IDNot Available
ChEBI ID12256  
Good Scents IDNot Available
References
General References
  1. Singh S, Upadhyay RK, Pandey MB, Singh JP, Pandey VB: Flavonoids from Echinops echinatus. J Asian Nat Prod Res. 2006 Apr-May;8(3):197-200. doi:  10.1080/1028602042000324826. [PubMed:16864424  ] 
  2. Park HY, Kim M, Han J: Stereospecific microbial production of isoflavanones from isoflavones and isoflavone glucosides. Appl Microbiol Biotechnol. 2011 Aug;91(4):1173-81. doi:  10.1007/s00253-011-3310-7. Epub 2011 May 12. [PubMed:21562980  ] 
  3. Itoh M, Hasegawa K, Fujiwara Y: Two-step laser excitation fluorescence study of the ground- and excited-state proton transfer in alcohol solutions of 7-hydroxyisoflavone. J Am Chem Soc. 1986 Sep 1;108(19):5853-7. doi: 10.1021/ja00279a032. [PubMed:22175340  ] 
  4. LOTUS database [Link]