NP-MRD: Showing NP-Card for 2'-Hydroxydaidzein (NP0045348)

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Record Information

Version

2.0

Created at

2022-03-17 19:18:23 UTC

Updated at

2022-03-17 19:18:23 UTC

NP-MRD ID

NP0045348

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxydaidzein

Description

2'-Hydroxydaidzein, also known as 2',4',7-thif, 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, 2'-hydroxydaidzein is considered to be a flavonoid lipid molecule. 2'-Hydroxydaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 2'-Hydroxydaidzein has been detected, but not quantified in, several different foods, such as common salsifies, rose hips, purslanes, hard wheats, and green vegetables. This could make 2'-hydroxydaidzein a potential biomarker for the consumption of these foods. 2'-Hydroxydaidzein is found in Crotalaria assamica, Crotalaria pallida , Eschscholzia californica , Pueraria candollei var. mirifica, Taxus chinensis, Taxus fuana, Taxus yunnanensis, Trifolium repens and Viola hondoensis. 2'-Hydroxydaidzein was first documented in 1990 (PMID: 2306102). A hydroxyisoflavone that is daidzein bearing an additional hydroxy substituent at position 2' (PMID: 15013012) (PMID: 9790908).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
   -0.1445    1.6293    0.8948 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4130    0.6238    0.3872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2923   -0.4569   -0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7286   -0.3754   -0.0880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3092    0.7907   -0.6219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6717    0.9616   -0.6561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4265   -0.0620   -0.1445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8152    0.1116   -0.1790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8893   -1.2062    0.3805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -1.3825    0.4174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9594   -2.5479    0.9569 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -1.5156   -0.6648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7036   -1.4876   -0.6813 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3987   -0.4895   -0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7888   -0.4884   -0.2396 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5100    0.5718    0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8921    0.5826    0.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8916    1.6825    0.8256 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5293    1.6782    0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7887    0.6236    0.3551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895    1.5826   -1.0198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1447    1.8452   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2652    0.9279   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4914   -2.0129    0.7859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9935   -2.7348    1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1267   -2.3946   -1.0880 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2779   -1.3521   -0.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4341   -0.1595   -0.1393 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4448    2.5159    1.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9986    2.5390    1.2920 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 10  4  2  0
  4  5  1  0
  5  6  2  0
  4  3  1  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 14 20  2  0
 20 19  1  0
 19 18  2  0
 18 16  1  0
 16 17  1  0
 16 15  2  0
 20  2  1  0
  2  1  2  0
  6  7  1  0
  2  3  1  0
 15 14  1  0
  8 23  1  0
  9 24  1  0
 11 25  1  0
  5 21  1  0
  6 22  1  0
 12 26  1  0
 19 30  1  0
 18 29  1  0
 17 28  1  0
 15 27  1  0
M  END


  Mrv0541 02241217022D          

 20 22  0  0  0  0            999 V2000
   -2.4553    0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4553    1.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408    1.4396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264    1.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0264    0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119    1.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026    1.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026    0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3119   -1.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1698    1.4396    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4026   -1.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171   -1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -1.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1171   -0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315    0.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -0.2104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5460   -1.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2605   -1.4479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 16  1  0  0  0  0
 10 11  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 19  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045348

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

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

> <INCHI_KEY>
ZCTNPCRBEWXCGP-UHFFFAOYSA-N

> <FORMULA>
C15H10O5

> <MOLECULAR_WEIGHT>
270.2369

> <EXACT_MASS>
270.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.554236751980273

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
2.4268723896666664

> <ALOGPS_LOGS>
-3.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.528055954362388

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.469292867148247

> <JCHEM_PKA_STRONGEST_BASIC>
-5.337537101228987

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.6829

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-hydroxydaidzein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.583   0.377   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.583   1.917   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.249   2.687   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.916   1.917   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.916   0.377   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.249  -0.393   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.582   2.687   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.752   1.917   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.752   0.377   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.582  -0.393   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.582  -1.933   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.917   2.687   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       0.752  -2.703   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.085  -1.933   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.419  -2.703   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.085  -0.393   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.419   0.377   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.753  -0.393   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.753  -1.933   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.086  -2.703   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    5    9   11                                                  
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13   14                                                            
CONECT   14   13   15   16                                                  
CONECT   15   14   19                                                       
CONECT   16    9   14   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   15   18   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2',4',7-Trihydroxyisoflavone	ChEBI
3-(2,4-Dihydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one	ChEBI
3-(2,4-Dihydroxyphenyl)-7-hydroxychromen-4-one	Kegg
3-(2,4-Dihydroxyphenyl)-7-hydroxy-4H-1-benzopyran-4-one, 9ci	HMDB
3-(2,4-Dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one	HMDB
7,2',4'-Trihydroxyisoflavone	HMDB
2',4',7-THIF	HMDB

Chemical Formula

C₁₅H₁₀O₅

Average Mass

270.2369 Da

Monoisotopic Mass

270.05282 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-4H-chromen-4-one

Traditional Name

2'-hydroxydaidzein

CAS Registry Number

7678-85-5

SMILES

OC1=CC(O)=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

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

InChI Key

ZCTNPCRBEWXCGP-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
Cicer arietinum	FooDB	PHYTOHUB
Crotalaria assamica	Plant	KNApSAcK
Crotalaria pallida	Plant	KNApSAcK
Eschscholzia californica	Plant	KNApSAcK
Glycine max	FooDB	PHYTOHUB
Lens culinaris	FooDB	PHYTOHUB
Phaseolus coccineus	FooDB	KNAPSACK
Phaseolus lunatus	FooDB	KNAPSACK
Phaseolus vulgaris	FooDB	KNAPSACK
Pisum sativum	FooDB	PHYTOHUB
Pueraria candollei var. mirifica	Plant	KNApSAcK
Taxus chinensis	Plant	KNApSAcK
Taxus fuana	Plant	KNApSAcK
Taxus wallichiana var. yunnanensis	Plant	KNApSAcK
Trifolium repens	Plant	KNApSAcK
Vicia faba	FooDB	PHYTOHUB
Vigna mungo	FooDB	KNAPSACK
Viola hondoensis	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
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavone (CHEBI:27479 )
isoflavones (C02495 )
Isoflavonoids (C02495 )
Isoflavonoids (LMPK12050083 )
a small molecule (2-HYDROXYDAIDZEIN )

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	ALOGPS
logP	2.43	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	6.47	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	26.55 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

HMDB0029372

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280520

PDB ID

Not Available

ChEBI ID

27479

Good Scents ID

Not Available

References

General References

Ko HH, Weng JR, Tsao LT, Yen MH, Wang JP, Lin CN: Anti-inflammatory flavonoids and pterocarpanoid from Crotalaria pallida and C. assamica. Bioorg Med Chem Lett. 2004 Feb 23;14(4):1011-4. doi: 10.1016/j.bmcl.2003.11.074. [PubMed:15013012 ]
Fischer D, Ebenau-Jehle C, Grisebach H: Phytoalexin synthesis in soybean: purification and characterization of NADPH:2'-hydroxydaidzein oxidoreductase from elicitor-challenged soybean cell cultures. Arch Biochem Biophys. 1990 Feb 1;276(2):390-5. doi: 10.1016/0003-9861(90)90737-j. [PubMed:2306102 ]
Akashi T, Aoki T, Ayabe S: CYP81E1, a cytochrome P450 cDNA of licorice (Glycyrrhiza echinata L.), encodes isoflavone 2'-hydroxylase. Biochem Biophys Res Commun. 1998 Oct 9;251(1):67-70. doi: 10.1006/bbrc.1998.9414. [PubMed:9790908 ]

Showing NP-Card for 2'-Hydroxydaidzein (NP0045348)

MOL for NP0045348 (2'-Hydroxydaidzein)

3D MOL for NP0045348 (2'-Hydroxydaidzein)

3D SDF for NP0045348 (2'-Hydroxydaidzein)

3D-SDF for NP0045348 (2'-Hydroxydaidzein)

PDB for NP0045348 (2'-Hydroxydaidzein)

3D PDB for NP0045348 (2'-Hydroxydaidzein)

SMILES for NP0045348 (2'-Hydroxydaidzein)

INCHI for NP0045348 (2'-Hydroxydaidzein)

Structure for NP0045348 (2'-Hydroxydaidzein)

3D Structure for NP0045348 (2'-Hydroxydaidzein)