NP-MRD: Showing NP-Card for 3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one (NP0296259)

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Record Information

Version

2.0

Created at

2022-09-10 05:43:58 UTC

Updated at

2022-09-10 05:43:58 UTC

NP-MRD ID

NP0296259

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one

Description

3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group. 3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231518442D          

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M  END

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M  END


  Mrv1533004231518442D          

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    4.0668    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2102    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 10  1  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 13 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 35 39  1  0  0  0  0
 39 40  2  0  0  0  0
 32 40  1  0  0  0  0
 27 41  2  0  0  0  0
 21 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296259

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CC1=CC=C(O)C=C1)C(C)C(C1=CC=C(O)C=C1)C1=C(O)C=C(O)C(C(=O)CCC2=CC=C3OCOC3=C2)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C34H34O8/c1-19(15-21-3-9-24(35)10-4-21)20(2)31(23-7-11-25(36)12-8-23)33-28(39)17-27(38)32(34(33)40)26(37)13-5-22-6-14-29-30(16-22)42-18-41-29/h3-4,6-12,14,16-17,19-20,31,35-36,38-40H,5,13,15,18H2,1-2H3

> <INCHI_KEY>
FAGZEPREVXXJOQ-UHFFFAOYSA-N

> <FORMULA>
C34H34O8

> <MOLECULAR_WEIGHT>
570.638

> <EXACT_MASS>
570.225368055

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
61.13756359810631

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

> <ALOGPS_LOGP>
5.20

> <JCHEM_LOGP>
8.635569962333332

> <ALOGPS_LOGS>
-5.50

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.90015057891314

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.647981708927859

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3819008211153685

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
158.73609999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      16.927   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.927   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.261   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      19.594   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.594   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      20.928   4.383   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      22.262   3.613   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.595   4.383   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      22.262   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.928   1.303   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      15.593   1.303   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      15.593  -0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.260   2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.260   3.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.926   4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.926   5.923   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.260   6.693   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      14.260   8.233   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      15.593   5.923   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.593   4.383   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      12.926   1.303   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.926  -0.237   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      14.260  -1.007   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.592  -1.007   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.259  -0.237   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.925  -1.007   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.259   1.303   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.925   2.073   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       7.591   1.303   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.925   3.613   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      11.592   2.073   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      11.592   3.613   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9    4                                                       
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   21                                                  
CONECT   14   13   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   14                                                       
CONECT   21   13   22   41                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   41                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   40                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   35   40                                                  
CONECT   40   39   32                                                       
CONECT   41   27   21   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₄H₃₄O₈

Average Mass

570.6380 Da

Monoisotopic Mass

570.22537 Da

IUPAC Name

3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

Traditional Name

3-(2H-1,3-benzodioxol-5-yl)-1-{2,4,6-trihydroxy-3-[1-(4-hydroxyphenyl)-3-[(4-hydroxyphenyl)methyl]-2-methylbutyl]phenyl}propan-1-one

CAS Registry Number

Not Available

SMILES

CC(CC1=CC=C(O)C=C1)C(C)C(C1=CC=C(O)C=C1)C1=C(O)C=C(O)C(C(=O)CCC2=CC=C3OCOC3=C2)=C1O

InChI Identifier

InChI=1S/C34H34O8/c1-19(15-21-3-9-24(35)10-4-21)20(2)31(23-7-11-25(36)12-8-23)33-28(39)17-27(38)32(34(33)40)26(37)13-5-22-6-14-29-30(16-22)42-18-41-29/h3-4,6-12,14,16-17,19-20,31,35-36,38-40H,5,13,15,18H2,1-2H3

InChI Key

FAGZEPREVXXJOQ-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 curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Curcuminoids

Alternative Parents

Substituents

Desmethoxycurcumin
Dibenzylbutane lignan skeleton
Norlignan skeleton
2'-hydroxy-dihydrochalcone
Alkyl-phenylketone
Diphenylmethane
Acylphloroglucinol derivative
Butyrophenone
Benzenetriol
Benzodioxole
Phenylketone
Phenylpropane
Phloroglucinol derivative
Aryl alkyl ketone
Aryl ketone
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Oxacycle
Polyol
Acetal
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	5.2	ALOGPS
logP	8.64	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	7.65	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	158.74 m³·mol⁻¹	ChemAxon
Polarizability	61.14 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one (NP0296259)

MOL for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

3D MOL for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

3D SDF for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

3D-SDF for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

PDB for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

3D PDB for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

SMILES for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

INCHI for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

Structure for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)

3D Structure for NP0296259 (3-(2h-1,3-benzodioxol-5-yl)-1-{3-[1,4-bis(4-hydroxyphenyl)-2,3-dimethylbutyl]-2,4,6-trihydroxyphenyl}propan-1-one)