NP-MRD: Showing NP-Card for 5,7,3',4'-Tetrahydroxyisoflavone (NP0051479)

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Record Information

Version

2.0

Created at

2022-04-27 22:49:48 UTC

Updated at

2022-04-27 22:49:48 UTC

NP-MRD ID

NP0051479

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7,3',4'-Tetrahydroxyisoflavone

Description

3'-Hydroxygenistein, also known as isoluteolin or norsantal, 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, 3'-hydroxygenistein is considered to be a flavonoid lipid molecule. 5,7,3',4'-Tetrahydroxyisoflavone is found in Ammopiptanthus mongolicus, Anaxagorea luzonensis, Anaxagorea luzonensis A.GRAY, Baptisia spp., Bolusanthus speciosus, Bolusanthus specious, Rosulabryum capillare, Calophyllum polyanthum, Cladrastis platycarpa, Cudrania cochinchinensis var. gerontogea , Cyclopia subternata, Cytisus scoparius , Dalbergia lanceolaria, Dalbergia odorifera , Dalbergia parviflora, Dermatophyllum secundiflorum, Erycibe expansa , Erythroxylum ulei, Flemingia macrophylla, Glycyrrhiza uralensis, Lathyrus montanus , Lathyrus nissolia, Lathyrus spp., Maackia amurensis , Cudrania cochinchinensis , Maclura tinctoria , Cudrania tricuspidata , Ophiocordyceps sinensis, Sophora secundiflora , Soroseris hookeriana, Stemphilium sp. No. 644, Streptomyces avermitilis, Streptomyces neyagawaensis, Styphnolobium japonicum, Thermopsis spp., Trifolium pratense and Wyethia angustifolia. 3'-Hydroxygenistein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.2442    1.8308   -0.1322 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5768    0.6262   -0.0785 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3055   -0.4260   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7282   -0.1191   -0.1828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2456    0.8054   -1.0488 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6117    1.0411   -1.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4863    0.3728   -0.2456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8581    0.6239   -0.2835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9546   -0.5524    0.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8388   -1.2359    1.4622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5939   -0.7961    0.6510 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1355   -1.7222   -0.0333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -1.9594    0.0431 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2841   -0.9910    0.0628 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6437   -1.3105    0.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6247   -0.3575    0.1723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9848   -0.6780    0.2563 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2277    0.9631    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.3155    0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4796    2.6428   -0.0337 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9190    0.3339    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5773    1.3481   -1.7130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9765    1.7729   -1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2259    1.3033   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5236   -1.9347    2.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2429   -1.5466    1.3651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5991   -2.5192   -0.0500 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9328   -2.3598    0.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2948   -1.6238    0.3012 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9870    1.7478    0.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1404    3.4046   -0.0200 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 21  2  0
 21 19  1  0
 19 20  1  0
 19 18  2  0
 21  2  1  0
  2  1  2  0
  2  3  1  0
  3 12  2  0
 12 13  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 18 16  1  0
 11  4  1  0
 13 14  1  0
 17 29  1  0
 15 28  1  0
 20 31  1  0
 18 30  1  0
 12 27  1  0
  5 22  1  0
  6 23  1  0
  8 24  1  0
 10 25  1  0
 11 26  1  0
M  END


  Mrv0541 02271201292D          

 21 23  0  0  0  0            999 V2000
    4.5012   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7867   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3578   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0722   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6433   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9291    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2146   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5001   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2143   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9288   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5012   -1.2375    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  2  0  0  0  0
  6  7  1  0  0  0  0
  2  7  2  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 11 18  2  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0051479

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H

> <INCHI_KEY>
IOYHCQBYQJQBSK-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.2363

> <EXACT_MASS>
286.047738052

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
27.53209482020776

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.64

> <JCHEM_LOGP>
2.773307068

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.58096078715371

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.604244293063947

> <JCHEM_PKA_STRONGEST_BASIC>
-5.179055343026602

> <JCHEM_POLAR_SURFACE_AREA>
107.22000000000001

> <JCHEM_REFRACTIVITY>
73.6638

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
quercitin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0       8.402  -5.390   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.069  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.069  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.735  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.401  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.401  -4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.735  -5.390   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.067  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.067  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.734   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.400  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.934   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.267  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -3.601   0.000   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -2.267  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.934  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.934  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.400  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.734  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.734  -4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.402  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11   19                                                  
CONECT   19   18    8   20                                                  
CONECT   20   19                                                            
CONECT   21    3                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
3',4',5,7-Tetrahydroxyisoflavone	ChEBI
5,7-Dihydroxy-3-(3,4-dihydroxyphenyl)-4-1H-benzopyran-4-one	ChEBI
Isoluteolin	ChEBI
Norsantal	ChEBI
Santol	ChEBI
3'-Hydroxygenistein	ChEBI
3-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one	MeSH

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2363 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

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

Traditional Name

quercitin

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(C(O)=C1)C(=O)C(=CO2)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H

InChI Key

IOYHCQBYQJQBSK-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
Ammopiptanthus mongolicus	LOTUS Database	35616633
Anaxagorea luzonensis	LOTUS Database	35616633
Anaxagorea luzonensis A.GRAY	Plant	KNApSAcK
Baptisia spp.	Plant	KNApSAcK
Bolusanthus speciosus	Plant	KNApSAcK
Bolusanthus specious	Plant	KNApSAcK
Bryum capillare	LOTUS Database	35616633
Calophyllum polyanthum	Plant	KNApSAcK
Cladrastis platycarpa	LOTUS Database	35616633
Cudrania cochinchinensis var. gerontogea	Plant	KNApSAcK
Cyclopia subternata	LOTUS Database	35616633
Cytisus scoparius	Plant	KNApSAcK
Dalbergia lanceolaria	LOTUS Database	35616633
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia parviflora	LOTUS Database	35616633
Dermatophyllum secundiflorum	LOTUS Database	35616633
Erycibe expansa	Plant	KNApSAcK
Erythroxylum ulei	Plant	KNApSAcK
Flemingia macrophylla	LOTUS Database	35616633
Glycyrrhiza uralensis	LOTUS Database	35616633
Lathyrus montanus	Plant	KNApSAcK
Lathyrus nissolia	Plant	KNApSAcK
Lathyrus spp.	Plant	KNApSAcK
Maackia amurensis	Plant	KNApSAcK
Maclura cochinchinensis	Plant	KNApSAcK
Maclura tinctoria	Plant	KNApSAcK
Maclura tricuspidata	Plant	KNApSAcK
Ophiocordyceps sinensis	LOTUS Database	35616633
Sophora secundiflora	Plant	KNApSAcK
Soroseris hookeriana	LOTUS Database	35616633
Stemphilium sp. No. 644	-	KNApSAcK
Streptomyces avermitilis	LOTUS Database	35616633
Streptomyces neyagawaensis	LOTUS Database	35616633
Styphnolobium japonicum	LOTUS Database	35616633
Thermopsis spp.	Plant	KNApSAcK
Trifolium pratense	LOTUS Database	35616633
Wyethia angustifolia	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
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyranone
Monocyclic benzene moiety
Pyran
Benzenoid
Heteroaromatic compound
Vinylogous acid
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:69437 )
isoflavones (C10510 )
Isoflavonoids (C10510 )
Isoflavonoids (LMPK12050251 )

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	2.64	ALOGPS
logP	2.77	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.6	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	107.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.66 m³·mol⁻¹	ChemAxon
Polarizability	27.53 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