NP-MRD: Showing NP-Card for 8-Hydroxydaidzein (NP0047769)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 20:45:39 UTC

Updated at

2022-03-17 20:45:39 UTC

NP-MRD ID

NP0047769

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Hydroxydaidzein

Description

8-Hydroxydaidzein, also known as NSC 678112, 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, 8-hydroxydaidzein is considered to be a flavonoid lipid molecule. 8-Hydroxydaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 8-Hydroxydaidzein has been detected, but not quantified in, pulses and soy beans. 8-Hydroxydaidzein is found in Eleutherococcus brachypus, Hedysarum theinum and Streptomyces sp. OH-1049. This could make 8-hydroxydaidzein a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652310011709192D          

 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
   10.0675   -4.8719    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
  3 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047769

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O

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

> <INCHI_KEY>
BMZFZTMWBCFKSS-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
26.663264493709512

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7,8-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
3.09

> <JCHEM_LOGP>
2.4268723896666664

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.964902814600421

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.7007541937492885

> <JCHEM_PKA_STRONGEST_BASIC>
-5.390418760554791

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.6829

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxydaidzein

> <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      18.793  -9.094   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7   20                                                  
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                                                       
CONECT   16   14   17                                                       
CONECT   17   15   18   16                                                  
CONECT   18   17                                                            
CONECT   19    7                                                            
CONECT   20    3                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
4'78-Trihydroxyisoflavone	HMDB
784'-Trihydroxyisoflavone	HMDB
4',7,8-Trihydroxyisoflavone	HMDB
7,8,4'-Trihydroxyisoflavone	HMDB
7,8-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-one	HMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	HMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9ci	HMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one	HMDB
7,8-Dihydroxy-3-(4-hydroxyphenyl)chromen-4-one	HMDB
NSC 678112	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

7,8-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Traditional Name

8-hydroxydaidzein

CAS Registry Number

75187-63-2

SMILES

OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2O)C1=O

InChI Identifier

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

InChI Key

BMZFZTMWBCFKSS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Eleutherococcus brachypus	LOTUS Database	35616633
Glycine max	FooDB	KNAPSACK
Hedysarum theinum	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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Isoflavonoids (LMPK12050137 )

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	3.09	ALOGPS
logP	2.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.7	ChemAxon
pKa (Strongest Basic)	-5.4	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

HMDB0033860

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012044

KNApSAcK ID

C00009852

Chemspider ID

4577542

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5466139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8-Hydroxydaidzein (NP0047769)

MOL for NP0047769 (8-Hydroxydaidzein)

3D MOL for NP0047769 (8-Hydroxydaidzein)

3D SDF for NP0047769 (8-Hydroxydaidzein)

3D-SDF for NP0047769 (8-Hydroxydaidzein)

PDB for NP0047769 (8-Hydroxydaidzein)

3D PDB for NP0047769 (8-Hydroxydaidzein)

SMILES for NP0047769 (8-Hydroxydaidzein)

INCHI for NP0047769 (8-Hydroxydaidzein)

Structure for NP0047769 (8-Hydroxydaidzein)

3D Structure for NP0047769 (8-Hydroxydaidzein)