NP-MRD: Showing NP-Card for 3'-Hydroxydaidzein (NP0056487)

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Record Information

Version

2.0

Created at

2022-04-28 02:15:43 UTC

Updated at

2022-04-28 02:15:43 UTC

NP-MRD ID

NP0056487

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-Hydroxydaidzein

Description

3'-Hydroxydaidzein 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'-hydroxydaidzein is considered to be a flavonoid lipid molecule. 3'-Hydroxydaidzein is found in Astragalus complanatus, Dalbergia odorifera , Dalbergia spruceana, Erycibe expansa , Glycyrrhiza glabra , Glycyrrhiza inflata , Glycyrrhiza uralensis , Hibiscus syriacus, Machaerium villosum, Medicago arabica, Muntingia calabura , Myroxylon peruiferum, Ophiocordyceps sinensis, Pueraria candollei var. mirifica, Sophora flavescens, Streptomyces cavourensis and Streptomyces sp. OH-1049. 3'-Hydroxydaidzein was first documented in 2009 (PMID: 19577190). 3'-Hydroxydaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 23265084) (PMID: 21378167).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.1256    0.2511   -1.5639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6254    0.0851   -0.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2049   -0.0036    0.6522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6528    0.0933    0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402    0.8595    1.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8146    0.9497    1.2168 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4375    0.2535    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8152    0.3404    0.0749 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6876   -0.5226   -0.6428 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3585   -1.2113   -1.6449 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3223   -0.5973   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025   -0.1894    1.8880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7042   -0.2781    2.0258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5250   -0.1981    1.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9087   -0.2965    1.1876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7523   -0.2104    0.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1105   -0.3140    0.3427 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1929   -0.0266   -1.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8237    0.0744   -1.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9942   -0.0155   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9531    1.4223    2.1586 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4310    1.5503    1.8729 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3720    0.8936    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8243   -1.7726   -2.2658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7757   -1.2048   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2460   -0.2591    2.7450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2424   -0.4396    2.1994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6521    0.5105    0.5334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8812    0.0385   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3953    0.2173   -2.3060 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 20  2  0
 20 19  1  0
 19 18  2  0
 20  2  1  0
  2  1  2  0
  2  3  1  0
  3 12  2  0
 12 13  1  0
  3  4  1  0
  4 11  2  0
 11  9  1  0
  9 10  1  0
  9  7  2  0
  7  8  1  0
  7  6  1  0
  6  5  2  0
 18 16  1  0
  5  4  1  0
 13 14  1  0
 17 28  1  0
 15 27  1  0
 19 30  1  0
 18 29  1  0
 12 26  1  0
 11 25  1  0
 10 24  1  0
  8 23  1  0
  6 22  1  0
  5 21  1  0
M  END


  Mrv1652310011709162D          

 20 22  0  0  0  0            999 V2000
   10.7820   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7820   -6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675   -5.6969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -5.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0675   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2109   -6.1094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2109   -6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4965   -8.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3531   -6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9254   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   -6.9343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9254   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3543   -7.3468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6398   -8.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3543   -8.1719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0688   -8.5844    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6386   -5.6969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0687   -6.9343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  4  8  1  0  0  0  0
  5  9  1  0  0  0  0
  5 10  2  0  0  0  0
  6 11  2  0  0  0  0
  7 19  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 13 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  2  0  0  0  0
 16 17  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056487

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
DDKGKOOLFLYZDL-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.659207815309998

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.4268723896666664

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.676157020101584

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.4751111499991385

> <JCHEM_PKA_STRONGEST_BASIC>
-5.33620244110205

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.68289999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3',4',7-trihydroxyisoflavone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 01-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-OCT-17         0                                  
HETATM    1  C   UNK     0      20.126 -11.404   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      20.126 -12.944   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.793 -10.634   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      21.460 -10.634   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      21.460 -13.714   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.793 -13.714   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.459 -11.404   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      22.794 -11.404   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.794 -12.944   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      21.460 -15.254   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      17.459 -12.944   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.127 -13.714   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.461 -12.944   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.127 -15.254   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.795 -13.714   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.461 -16.024   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.795 -15.254   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      28.128 -16.024   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.125 -10.634   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      28.128 -12.944   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8                                                       
CONECT    5    2    9   10                                                  
CONECT    6    2   11                                                       
CONECT    7    3   19   11                                                  
CONECT    8    4    9                                                       
CONECT    9    5   12    8                                                  
CONECT   10    5                                                            
CONECT   11    6    7                                                       
CONECT   12    9   13   14                                                  
CONECT   13   12   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   20                                                  
CONECT   16   14   17                                                       
CONECT   17   15   18   16                                                  
CONECT   18   17                                                            
CONECT   19    7                                                            
CONECT   20   15                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
3-(3,4-Dihydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one	ChEBI
3',4',7-Trihydroxyisoflavone	MeSH
7,3',4'-Trihydroxyisoflavone	MeSH

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

3-(3,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one

Traditional Name

3',4',7-trihydroxyisoflavone

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

DDKGKOOLFLYZDL-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
Astragalus complanatus	LOTUS Database	35616633
Dalbergia odorifera	Plant	KNApSAcK
Dalbergia spruceana	LOTUS Database	35616633
Erycibe expansa	Plant	KNApSAcK
Glycyrrhiza glabra	Plant	KNApSAcK
Glycyrrhiza inflata	Plant	KNApSAcK
Glycyrrhiza uralensis	Plant	KNApSAcK
Hibiscus syriacus	LOTUS Database	35616633
Machaerium villosum	Plant	KNApSAcK
Medicago arabica	Plant	KNApSAcK
Muntingia calabura	Plant	KNApSAcK
Myroxylon peruiferum	LOTUS Database	35616633
Ophiocordyceps sinensis	LOTUS Database	35616633
Pueraria candollei var. mirifica	Plant	KNApSAcK
Sophora flavescens	LOTUS Database	35616633
Streptomyces cavourensis	LOTUS Database	35616633
Streptomyces sp. OH-1049	Bacteria	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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:50399 )
isoflavones (C14313 )
Isoflavonoids (LMPK12050055 )

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	3.05	ALOGPS
logP	2.43	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.48	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	26.66 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

HMDB0041655

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5284648

PDB ID

47X

ChEBI ID

50399

Good Scents ID

Not Available

References

General References

Bae M, Woo M, Kusuma IW, Arung ET, Yang CH, Kim YU: Inhibitory effects of isoflavonoids on rat prostate testosterone 5alpha-reductase. J Acupunct Meridian Stud. 2012 Dec;5(6):319-22. doi: 10.1016/j.jams.2012.07.022. Epub 2012 Aug 9. [PubMed:23265084 ]
Roh C, Seo SH, Choi KY, Cha M, Pandey BP, Kim JH, Park JS, Kim DH, Chang IS, Kim BG: Regioselective hydroxylation of isoflavones by Streptomyces avermitilis MA-4680. J Biosci Bioeng. 2009 Jul;108(1):41-6. doi: 10.1016/j.jbiosc.2009.02.021. [PubMed:19577190 ]
Lee DE, Lee KW, Byun S, Jung SK, Song N, Lim SH, Heo YS, Kim JE, Kang NJ, Kim BY, Bowden GT, Bode AM, Lee HJ, Dong Z: 7,3',4'-Trihydroxyisoflavone, a metabolite of the soy isoflavone daidzein, suppresses ultraviolet B-induced skin cancer by targeting Cot and MKK4. J Biol Chem. 2011 Apr 22;286(16):14246-56. doi: 10.1074/jbc.M110.147348. Epub 2011 Mar 4. [PubMed:21378167 ]

Showing NP-Card for 3'-Hydroxydaidzein (NP0056487)

MOL for NP0056487 (3'-Hydroxydaidzein)

3D MOL for NP0056487 (3'-Hydroxydaidzein)

3D SDF for NP0056487 (3'-Hydroxydaidzein)

3D-SDF for NP0056487 (3'-Hydroxydaidzein)

PDB for NP0056487 (3'-Hydroxydaidzein)

3D PDB for NP0056487 (3'-Hydroxydaidzein)

SMILES for NP0056487 (3'-Hydroxydaidzein)

INCHI for NP0056487 (3'-Hydroxydaidzein)

Structure for NP0056487 (3'-Hydroxydaidzein)

3D Structure for NP0056487 (3'-Hydroxydaidzein)