NP-MRD: Showing NP-Card for Dihydrodaidzein (NP0136929)

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Record Information

Version

2.0

Created at

2022-05-30 16:28:43 UTC

Updated at

2022-05-30 16:28:43 UTC

NP-MRD ID

NP0136929

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrodaidzein

Description

Dihydrodaidzein 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, dihydrodaidzein is considered to be a flavonoid lipid molecule. Dihydrodaidzein is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Dihydrodaidzein has been detected, but not quantified in, several different foods, such as chinese cinnamons, chervils, epazotes, rosemaries, and cloves. This could make dihydrodaidzein a potential biomarker for the consumption of these foods. Dihydrodaidzein was first documented in 2002 (PMID: 12270199). A hydroxyisoflavanone that is isoflavanone carrying two hydroxy substituents located at positions 4' and 7 (PMID: 21626023) (PMID: 23542626) (PMID: 24010344).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    0.0349    0.0222   -2.2532 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3821   -0.4302   -1.1574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691   -0.1933   -0.8087 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7134    0.2243   -1.7083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0272    0.4457   -1.3648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3920    0.2292   -0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7127    0.4366    0.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4348   -0.1903    0.8584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1414   -0.4037    0.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1515   -0.8269    1.3781 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0312   -1.5755    1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5726   -1.1712   -0.3036 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8270   -0.4114   -0.1274 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0213   -0.8861   -0.6119 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2102   -0.1707   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1703    1.0328    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732    1.7322    0.3683 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831    1.5380    0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    0.7958    0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    0.3945   -2.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7760    0.7701   -2.0480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0293    1.3201    0.7140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7063   -0.3654    1.9087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7321   -1.4296    1.8341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -2.6481    1.0163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8073   -2.1226   -0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0439   -1.8328   -1.1316 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -0.5484   -0.8327 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3913    2.6116    0.8436 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811    2.4897    1.2334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8835    1.1632    0.9083 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 13  2  0
 13 19  1  0
 19 18  2  0
 13 12  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  3  2  1  0
  2  1  2  0
 18 16  1  0
  2 12  1  0
  8  9  1  0
 17 29  1  0
 15 28  1  0
 14 27  1  0
 19 31  1  0
 18 30  1  0
 12 26  1  6
 11 24  1  0
 11 25  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  8 23  1  0
M  END

  Mrv0541 02231220282D          

 19 21  0  0  0  0            999 V2000
   17.8603   -3.4652    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8603   -5.9401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7725   -3.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2881   -6.3526    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1458   -3.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8603   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4315   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5748   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5748   -3.8777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4315   -5.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7171   -4.7026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3122   -5.1438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3122   -3.4367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0596   -4.7198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0596   -3.8606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7171   -6.3526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0026   -5.1151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0026   -5.9401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1 10  1  0  0  0  0
  2  7  2  0  0  0  0
  3 16  1  0  0  0  0
  4 19  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 11  2  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 17  1  0  0  0  0
 12 18  2  0  0  0  0
 13 15  2  0  0  0  0
 14 16  2  0  0  0  0
 15 16  1  0  0  0  0
 17 19  2  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0136929

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

> <INCHI_KEY>
JHYXBPPMXZIHKG-UHFFFAOYSA-N

> <FORMULA>
C15H12O4

> <MOLECULAR_WEIGHT>
256.2534

> <EXACT_MASS>
256.073558872

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
25.761430116176626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
2.3812234356666666

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.501081398648399

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.775319135909201

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9060041662312335

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
69.69560000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+/-)-dihydrodaidzein

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      33.339  -6.468   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      33.339 -11.088   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      38.775  -6.431   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      26.671 -11.858   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      32.005  -8.778   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      32.005  -7.238   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.339  -9.548   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.672  -9.548   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      34.673  -8.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      34.673  -7.238   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.672 -11.088   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      29.339  -8.778   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.049  -9.602   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.049  -6.415   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.445  -8.810   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.445  -7.206   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.339 -11.858   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.005  -9.548   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.005 -11.088   0.000  0.00  0.00           C+0
CONECT    1    6   10                                                       
CONECT    2    7                                                            
CONECT    3   16                                                            
CONECT    4   19                                                            
CONECT    5    6    7    8                                                  
CONECT    6    1    5                                                       
CONECT    7    2    5    9                                                  
CONECT    8    5   11   12                                                  
CONECT    9    7   10   13                                                  
CONECT   10    1    9   14                                                  
CONECT   11    8   17                                                       
CONECT   12    8   18                                                       
CONECT   13    9   15                                                       
CONECT   14   10   16                                                       
CONECT   15   13   16                                                       
CONECT   16    3   14   15                                                  
CONECT   17   11   19                                                       
CONECT   18   12   19                                                       
CONECT   19    4   17   18                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Value	Source
(+/-)-dihydrodaidzein	ChEBI
2,3-Dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
7,4'-Dihydroxyisoflavanone	ChEBI
4',7-Dihydroxy-isoflavanone	HMDB

Chemical Formula

C₁₅H₁₂O₄

Average Mass

256.2534 Da

Monoisotopic Mass

256.07356 Da

IUPAC Name

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

Traditional Name

(+/-)-dihydrodaidzein

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2

InChI Key

JHYXBPPMXZIHKG-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxyisoflavanone (CHEBI:75842 )
Isoflavonoids (LMPK12050447 )
an isoflavone (CPD-12609 )

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	2.77	ALOGPS
logP	2.38	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.78	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.76 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

HMDB0005760

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030168

KNApSAcK ID

Not Available

Chemspider ID

154076

KEGG Compound ID

Not Available

BioCyc ID

2-HYDROXY-23-DIHYDRODAIDZEIN

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

176907

PDB ID

Not Available

ChEBI ID

75842

Good Scents ID

Not Available

References

General References

Zhao H, Wang XL, Zhang HL, Li CD, Wang SY: Production of dihydrodaidzein and dihydrogenistein by a novel oxygen-tolerant bovine rumen bacterium in the presence of atmospheric oxygen. Appl Microbiol Biotechnol. 2011 Nov;92(4):803-13. doi: 10.1007/s00253-011-3278-3. Epub 2011 May 29. [PubMed:21626023 ]
Franke AA, Custer LJ, Wilkens LR, Le Marchand LL, Nomura AM, Goodman MT, Kolonel LN: Liquid chromatographic-photodiode array mass spectrometric analysis of dietary phytoestrogens from human urine and blood. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Sep 25;777(1-2):45-59. doi: 10.1016/s1570-0232(02)00216-7. [PubMed:12270199 ]
Schroder C, Matthies A, Engst W, Blaut M, Braune A: Identification and expression of genes involved in the conversion of daidzein and genistein by the equol-forming bacterium Slackia isoflavoniconvertens. Appl Environ Microbiol. 2013 Jun;79(11):3494-502. doi: 10.1128/AEM.03693-12. Epub 2013 Mar 29. [PubMed:23542626 ]
Sun Y, Li T, Ma C: [Separation of racemic flavonoids by high performance liquid chromatography using chiral mobile phase additive]. Se Pu. 2013 May;31(5):447-50. doi: 10.3724/sp.j.1123.2012.12054. [PubMed:24010344 ]

Showing NP-Card for Dihydrodaidzein (NP0136929)

MOL for NP0136929 (Dihydrodaidzein)

3D MOL for NP0136929 (Dihydrodaidzein)

3D SDF for NP0136929 (Dihydrodaidzein)

3D-SDF for NP0136929 (Dihydrodaidzein)

PDB for NP0136929 (Dihydrodaidzein)

3D PDB for NP0136929 (Dihydrodaidzein)

SMILES for NP0136929 (Dihydrodaidzein)

INCHI for NP0136929 (Dihydrodaidzein)

Structure for NP0136929 (Dihydrodaidzein)

3D Structure for NP0136929 (Dihydrodaidzein)