NP-MRD: Showing NP-Card for 5,7,3'-Trihydroxyisoflavone (NP0056838)

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Record Information

Version

2.0

Created at

2022-04-28 02:28:37 UTC

Updated at

2022-04-28 02:28:37 UTC

NP-MRD ID

NP0056838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,3'-Trihydroxyisoflavone

Description

5,7-Dihydroxy-3-(3-hydroxyphenyl)-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. Thus, 5,7-dihydroxy-3-(3-hydroxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7,3'-Trihydroxyisoflavone is found in Lupinus hirsutus . 5,7-Dihydroxy-3-(3-hydroxyphenyl)-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

 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.0105   -1.8129    0.0242 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4337   -0.6411    0.0492 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4673    0.4196   -0.1150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8714    0.0995   -0.3057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2835   -0.8809   -1.1556 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6448   -1.1252   -1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5766   -0.3995   -0.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1471    0.6009    0.2988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0384    1.3644    1.0435 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7922    0.8354    0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0360    1.6799   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3096    1.9248    0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1752    0.9768    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4858    1.3061    0.4224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4039    0.3006    0.5872 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7486    0.6446    0.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0069   -1.0124    0.5736 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6560   -1.3834    0.3922 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3110   -2.6894    0.3859 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7665   -0.3500    0.2306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5597   -1.4641   -1.7274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0198   -1.8976   -1.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6256   -0.6079   -0.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3487    1.0997    1.9729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4800    1.6118    1.0903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184    2.5205   -0.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8502    2.3361    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0426    1.5969    0.7792 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7139   -1.8038    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5443   -3.2495    0.2945 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4 10  2  0
  4  3  1  0
  3 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20  2  1  0
  2  1  2  0
 10  8  1  0
  2  3  1  0
 20 13  1  0
  9 24  1  0
  7 23  1  0
  6 22  1  0
  5 21  1  0
 10 25  1  0
 11 26  1  0
 14 27  1  0
 16 28  1  0
 17 29  1  0
 19 30  1  0
M  END


  Mrv1652308211911442D          

 20 22  0  0  0  0            999 V2000
    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
    5.7158    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
    5.7158    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
    6.4302    2.0625    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
    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
  8  2  1  0  0  0  0
  8  4  2  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  5  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 13  6  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  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20  7  1  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O5/c16-9-3-1-2-8(4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

> <INCHI_KEY>
QZKOCYLFGKLBDU-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.24

> <EXACT_MASS>
270.052823422

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.524435568767757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-3-(3-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.03

> <JCHEM_LOGP>
3.076872389666666

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.057427416111338

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.544759871001399

> <JCHEM_PKA_STRONGEST_BASIC>
-5.345751732911912

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
71.6829

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5,7-dihydroxy-3-(3-hydroxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 21-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   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      12.003   3.850   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.667   6.160   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       5.335   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    8                                                       
CONECT    3    1    9                                                       
CONECT    4    8    9                                                       
CONECT    5   10   12                                                       
CONECT    6   10   13                                                       
CONECT    7   11   20                                                       
CONECT    8    2    4   11                                                  
CONECT    9    3    4   16                                                  
CONECT   10    5    6   17                                                  
CONECT   11    7    8   15                                                  
CONECT   12    5   14   18                                                  
CONECT   13    6   14   20                                                  
CONECT   14   12   13   15                                                  
CONECT   15   11   14   19                                                  
CONECT   16    9                                                            
CONECT   17   10                                                            
CONECT   18   12                                                            
CONECT   19   15                                                            
CONECT   20    7   13                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2400 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

5,7-dihydroxy-3-(3-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

5,7-dihydroxy-3-(3-hydroxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

OC1=CC=CC(=C1)C1=COC2=CC(O)=CC(O)=C2C1=O

InChI Identifier

InChI=1S/C15H10O5/c16-9-3-1-2-8(4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

InChI Key

QZKOCYLFGKLBDU-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
Lupinus hirsutus	Plant	KNApSAcK

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
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050161 )

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	3.03	ALOGPS
logP	3.08	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.54	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.68 m³·mol⁻¹	ChemAxon
Polarizability	26.52 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

HMDB0129338

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB088189

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

9795414

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7,3'-Trihydroxyisoflavone (NP0056838)

MOL for NP0056838 (5,7,3'-Trihydroxyisoflavone)

3D MOL for NP0056838 (5,7,3'-Trihydroxyisoflavone)

3D SDF for NP0056838 (5,7,3'-Trihydroxyisoflavone)

3D-SDF for NP0056838 (5,7,3'-Trihydroxyisoflavone)

PDB for NP0056838 (5,7,3'-Trihydroxyisoflavone)

3D PDB for NP0056838 (5,7,3'-Trihydroxyisoflavone)

SMILES for NP0056838 (5,7,3'-Trihydroxyisoflavone)

INCHI for NP0056838 (5,7,3'-Trihydroxyisoflavone)

Structure for NP0056838 (5,7,3'-Trihydroxyisoflavone)

3D Structure for NP0056838 (5,7,3'-Trihydroxyisoflavone)