NP-MRD: Showing NP-Card for 2'-Hydroxydihydrodaidzein (NP0047790)

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Record Information

Version

2.0

Created at

2022-03-17 20:46:01 UTC

Updated at

2022-03-17 20:46:01 UTC

NP-MRD ID

NP0047790

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxydihydrodaidzein

Description

(±)-2'-Hydroxydihydrodaidzein, also known as 2',4',7-trihydroxyisoflavanone, belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4. Thus, (±)-2'-hydroxydihydrodaidzein is considered to be a flavonoid lipid molecule (±)-2'-Hydroxydihydrodaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (±)-2'-Hydroxydihydrodaidzein has been detected, but not quantified in, several different foods, such as pineapples, common wheats, pepper (c. Pubescens), common verbena, and dates. This could make (±)-2'-hydroxydihydrodaidzein a potential biomarker for the consumption of these foods. 2'-Hydroxydihydrodaidzein is found in Trifolium repens . 2'-Hydroxydihydrodaidzein was first documented in 1990 (PMID: 2306102). A hydroxyisoflavanone that is 2,3-dihydrodaidzein with an additonal hydroxy substituent at position 2'.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307272D          

 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
    0.7145    2.0625    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
    1.4289    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
    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
    5.7158    3.3000    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
    4.2868    2.4750    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
    3.5724    2.0625    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
    2.1434    1.2375    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    3.7125    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
    5.0013    1.2375    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
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  8  1  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
  9  6  2  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  1  0  0  0  0
 13  5  1  0  0  0  0
 13 10  2  0  0  0  0
 14  6  1  0  0  0  0
 14 11  2  0  0  0  0
 15 11  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 13  1  0  0  0  0
 19 15  2  0  0  0  0
 20  7  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047790

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O5/c16-8-1-3-10(13(18)5-8)12-7-20-14-6-9(17)2-4-11(14)15(12)19/h1-6,12,16-18H,7H2

> <INCHI_KEY>
WBOWBLGZAXVREM-UHFFFAOYSA-N

> <FORMULA>
C15H12O5

> <MOLECULAR_WEIGHT>
272.2528

> <EXACT_MASS>
272.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
26.614178811124965

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(2,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.0776581139999997

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.10194503811013

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.76199528267007

> <JCHEM_PKA_STRONGEST_BASIC>
-4.906023005242078

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
71.6765

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2'-hydroxydihydrodaidzein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   4.620   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      10.669   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   2.310   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   6.930   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       9.336   2.310   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    3    8                                                       
CONECT    2    4    9                                                       
CONECT    3    1   10                                                       
CONECT    4    2   11                                                       
CONECT    5    8   13                                                       
CONECT    6    9   14                                                       
CONECT    7   12   20                                                       
CONECT    8    1    5   16                                                  
CONECT    9    2    6   17                                                  
CONECT   10    3   12   13                                                  
CONECT   11    4   14   15                                                  
CONECT   12    7   10   15                                                  
CONECT   13    5   10   18                                                  
CONECT   14    6   11   20                                                  
CONECT   15   11   12   19                                                  
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20    7   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
2',4',7-Trihydroxyisoflavanone	ChEBI
2'-Hydroxydihydrodaidzein	ChEBI
2'-Hydroxy-2,3-dihydrodaidzein	Kegg

Chemical Formula

C₁₅H₁₂O₅

Average Mass

272.2528 Da

Monoisotopic Mass

272.06847 Da

IUPAC Name

3-(2,4-dihydroxyphenyl)-7-hydroxy-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

2'-hydroxydihydrodaidzein

CAS Registry Number

94388-77-9

SMILES

OC1=CC(O)=C(C=C1)C1COC2=C(C=CC(O)=C2)C1=O

InChI Identifier

InChI=1S/C15H12O5/c16-8-1-3-10(13(18)5-8)12-7-20-14-6-9(17)2-4-11(14)15(12)19/h1-6,12,16-18H,7H2

InChI Key

WBOWBLGZAXVREM-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Phaseolus coccineus	FooDB	KNAPSACK
Phaseolus vulgaris	FooDB	KNAPSACK
Trifolium repens	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavanones. These are polycyclic compounds containing an isoflavan skeleton which bears a ketone at position C4.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflavans

Direct Parent

Isoflavanones

Alternative Parents

Substituents

Isoflavanone
Isoflavanol
Hydroxyisoflavonoid
Chromone
1-benzopyran
Chromane
Benzopyran
Resorcinol
Aryl ketone
Aryl alkyl ketone
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Ketone
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:16035 )
isoflavanones (C03567 )
Isoflavonoids (C03567 )
Isoflavonoids (LMPK12050463 )
a small molecule (2-HYDROXY-23-DIHYDRODAIDZEIN )

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	2.37	ALOGPS
logP	2.08	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	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	26.61 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

HMDB0033928

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

2-HYDROXY-23-DIHYDRODAIDZEIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440047

PDB ID

Not Available

ChEBI ID

16035

Good Scents ID

Not Available

References

General References

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 ]

Showing NP-Card for 2'-Hydroxydihydrodaidzein (NP0047790)

MOL for NP0047790 (2'-Hydroxydihydrodaidzein)

3D MOL for NP0047790 (2'-Hydroxydihydrodaidzein)

3D SDF for NP0047790 (2'-Hydroxydihydrodaidzein)

3D-SDF for NP0047790 (2'-Hydroxydihydrodaidzein)

PDB for NP0047790 (2'-Hydroxydihydrodaidzein)

3D PDB for NP0047790 (2'-Hydroxydihydrodaidzein)

SMILES for NP0047790 (2'-Hydroxydihydrodaidzein)

INCHI for NP0047790 (2'-Hydroxydihydrodaidzein)

Structure for NP0047790 (2'-Hydroxydihydrodaidzein)

3D Structure for NP0047790 (2'-Hydroxydihydrodaidzein)