NP-MRD: Showing NP-Card for 2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone (NP0055356)

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Record Information

Version

2.0

Created at

2022-04-28 01:26:03 UTC

Updated at

2022-04-28 01:26:03 UTC

NP-MRD ID

NP0055356

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone

Description

Myrigalone E belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, myrigalone e is considered to be a flavonoid lipid molecule. Myrigalone E is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Myrigalone E has been detected, but not quantified in, herbs and spices. 2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone is found in Morella serrata and Myrica gale . This could make myrigalone e a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.4544    0.7565    1.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1207   -0.0024    0.4947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8021   -0.2043    0.0953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7708    0.3426    0.8241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4591    0.1602    0.4543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4080    0.7016    1.1752 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7185    1.4624    2.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1010   -0.5860   -0.6757 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2895   -0.7539   -1.0244 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5904   -1.4303   -2.0331 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4316   -0.1963   -0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7179   -0.6361   -0.9553 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9195   -0.1089   -0.2694 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5605   -0.7741    0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6831   -0.2083    1.3417 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1801    1.0161    0.9302 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5196    1.6737   -0.1019 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4075    1.1033   -0.6804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1307   -1.1321   -1.4032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9859   -1.8925   -2.5372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4732   -0.9354   -1.0097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5927   -1.5296   -1.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0745    1.7961    1.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5620    0.7420    1.7206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0390    0.3280    2.5670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9631    0.9306    1.7072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3131    0.8017    3.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1740    1.8646    2.8273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4222    2.2798    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4159    0.8978   -0.1709 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4418   -0.6236    0.7263 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7502   -1.7439   -0.9090 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7564   -0.3681   -2.0297 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1816   -1.7137    1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2191   -0.6978    2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0560    1.4727    1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9114    2.6386   -0.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9255    1.6651   -1.4900 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528   -2.1365   -2.9624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0214   -2.4237   -1.2887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2105   -1.8046   -2.8044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3558   -0.7315   -1.9609 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 21  3  1  0
 18 13  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 20 39  1  0
 22 40  1  0
 22 41  1  0
 22 42  1  0
M  END


  Mrv0541 05061305292D          

 22 23  0  0  0  0            999 V2000
   -0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
 10  9  1  0  0  0  0
 12  1  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  2  0  0  0  0
 15 12  1  0  0  0  0
 16 11  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18 12  2  0  0  0  0
 18 17  1  0  0  0  0
 19 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21 15  1  0  0  0  0
 22  3  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0055356

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O4/c1-12-15(21-2)11-16(22-3)17(18(12)20)14(19)10-9-13-7-5-4-6-8-13/h4-8,11,20H,9-10H2,1-3H3

> <INCHI_KEY>
ACLIVQJKNNTVHO-UHFFFAOYSA-N

> <FORMULA>
C18H20O4

> <MOLECULAR_WEIGHT>
300.349

> <EXACT_MASS>
300.136159128

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.89417693098896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylpropan-1-one

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
4.354315355666666

> <ALOGPS_LOGS>
-3.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.903672319731914

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.498055535656231

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6925102648093704

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
85.73219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylpropan-1-one

> <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      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  15.400   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335  15.400   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  15.400   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  13.090   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  13.860   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   21                                                            
CONECT    3   22                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5   13                                                       
CONECT    8    6   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   14                                                       
CONECT   11   15   16                                                       
CONECT   12    1   15   18                                                  
CONECT   13    7    8    9                                                  
CONECT   14   10   17   19                                                  
CONECT   15   11   12   21                                                  
CONECT   16   11   17   22                                                  
CONECT   17   14   16   18                                                  
CONECT   18   12   17   20                                                  
CONECT   19   14                                                            
CONECT   20   18                                                            
CONECT   21    2   15                                                       
CONECT   22    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
1-(2-Hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenyl-1-propanone	HMDB
2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone	HMDB

Chemical Formula

C₁₈H₂₀O₄

Average Mass

300.3490 Da

Monoisotopic Mass

300.13616 Da

IUPAC Name

1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylpropan-1-one

Traditional Name

1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-phenylpropan-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1C

InChI Identifier

InChI=1S/C18H20O4/c1-12-15(21-2)11-16(22-3)17(18(12)20)14(19)10-9-13-7-5-4-6-8-13/h4-8,11,20H,9-10H2,1-3H3

InChI Key

ACLIVQJKNNTVHO-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
Morella serrata	LOTUS Database	35616633
Myrica gale	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

2'-Hydroxy-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
Phenylketone
Anisole
Benzoyl
Phenoxy compound
O-cresol
Phenol ether
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
Toluene
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120488 )

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	3.66	ALOGPS
logP	4.35	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	10.5	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	85.73 m³·mol⁻¹	ChemAxon
Polarizability	32.89 Å³	ChemAxon
Number of Rings	2	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

HMDB0030755

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002687

KNApSAcK ID

C00007995

Chemspider ID

10229959

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15747330

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone (NP0055356)

MOL for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

3D MOL for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

3D SDF for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

3D-SDF for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

PDB for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

3D PDB for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

SMILES for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

INCHI for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

Structure for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)

3D Structure for NP0055356 (2'-Hydroxy-4',6'-dimethoxy-3'-methyldihydrochalcone)