NP-MRD: Showing NP-Card for 4,4'-Dihydroxy-2',6'-dimethoxychalcone (NP0054659)

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Record Information

Version

2.0

Created at

2022-04-28 00:56:50 UTC

Updated at

2022-04-28 00:56:50 UTC

NP-MRD ID

NP0054659

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,4'-Dihydroxy-2',6'-dimethoxychalcone

Description

4,4'-Dihydroxy-2',6'-dimethoxychalcone belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Thus, 4,4'-dihydroxy-2',6'-dimethoxychalcone is considered to be a flavonoid lipid molecule. 4,4'-Dihydroxy-2',6'-dimethoxychalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4,4'-Dihydroxy-2',6'-dimethoxychalcone has been detected, but not quantified in, alcoholic beverages. 4,4'-Dihydroxy-2',6'-dimethoxychalcone is found in Alpinia blepharocalyx, Humulus lupulus and Vitex tripinnata. This could make 4,4'-dihydroxy-2',6'-dimethoxychalcone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -2.2625   -2.7104   -2.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -2.1201   -1.1334 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552   -0.8353   -0.7630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0528   -0.1305   -1.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284    1.1485   -1.3112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2220    1.9236   -2.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0409    1.7239   -0.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519    1.0130    0.7769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8575    1.5908    1.9939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2748    2.9061    2.3048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731   -0.2621    0.4274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0514   -1.0090    1.3443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5849   -1.7355    2.2272 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148   -0.9765    1.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0896   -0.2587    0.4434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5425   -0.1831    0.3610 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4082   -0.8557    1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7740   -0.7848    1.1102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3490   -0.0021    0.1593 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7390    0.0800    0.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5339    0.7010   -0.7039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1616    0.6152   -0.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9293   -2.0736   -3.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8060   -3.7211   -2.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3726   -2.8353   -2.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3686   -0.5545   -2.6126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5487    1.5894   -3.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3288    2.7235    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008    3.6514    1.5611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    2.9232    2.2126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9502    3.1658    3.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9689   -1.5605    2.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4620    0.3128   -0.2581 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9802   -1.4842    1.9512 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3732   -1.3489    1.8024 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2649    0.7919    0.5920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0042    1.3241   -1.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5715    1.1791   -1.3004 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
  5  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  2  0
 11  3  1  0
 22 16  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 14 32  1  0
 15 33  1  0
 17 34  1  0
 18 35  1  0
 20 36  1  0
 21 37  1  0
 22 38  1  0
M  END

  Mrv0541 05061310402D          

 22 23  0  0  0  0            999 V2000
    2.8579    0.0000    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
    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
    2.8579    2.4750    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
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    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
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    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
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  2  0  0  0  0
 11  3  2  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  2  0  0  0  0
 12  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 10  2  0  0  0  0
 17 14  1  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21  1  1  0  0  0  0
 21 15  1  0  0  0  0
 22  2  1  0  0  0  0
 22 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054659

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC(OC)=C1C(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-21-15-9-13(19)10-16(22-2)17(15)14(20)8-5-11-3-6-12(18)7-4-11/h3-10,18-19H,1-2H3/b8-5+

> <INCHI_KEY>
SJULMVKFURWCFM-VMPITWQZSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.3059

> <EXACT_MASS>
300.099773622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
31.177978498533975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxy-2,6-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

> <ALOGPS_LOGP>
3.43

> <JCHEM_LOGP>
2.967852134333333

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.072456305562264

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.956542971744601

> <JCHEM_PKA_STRONGEST_BASIC>
-4.59544427100153

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
83.7652

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.84e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(4-hydroxy-2,6-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-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       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  10.780   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.003  -0.770   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
HETATM   21  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    6   11                                                       
CONECT    4    7   11                                                       
CONECT    5    8   11                                                       
CONECT    6    3   12                                                       
CONECT    7    4   12                                                       
CONECT    8    5   14                                                       
CONECT    9   13   15                                                       
CONECT   10   13   16                                                       
CONECT   11    3    4    5                                                  
CONECT   12    6    7   18                                                  
CONECT   13    9   10   19                                                  
CONECT   14    8   17   20                                                  
CONECT   15    9   17   21                                                  
CONECT   16   10   17   22                                                  
CONECT   17   14   15   16                                                  
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21    1   15                                                       
CONECT   22    2   16                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3059 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

(2E)-1-(4-hydroxy-2,6-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

Traditional Name

(2E)-1-(4-hydroxy-2,6-dimethoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC(OC)=C1C(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C17H16O5/c1-21-15-9-13(19)10-16(22-2)17(15)14(20)8-5-11-3-6-12(18)7-4-11/h3-10,18-19H,1-2H3/b8-5+

InChI Key

SJULMVKFURWCFM-VMPITWQZSA-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
Alpinia blepharocalyx	LOTUS Database	35616633
Humulus lupulus	Plant	KNApSAcK
Vitex tripinnata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Cinnamylphenols

Direct Parent

Cinnamylphenols

Alternative Parents

Substituents

Cinnamylphenol
Hydroxycinnamic acid or derivatives
Methoxyphenol
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Anisole
Benzoyl
Methoxybenzene
Phenol ether
Aryl ketone
Styrene
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120319 )

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	3.43	ALOGPS
logP	2.97	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	83.77 m³·mol⁻¹	ChemAxon
Polarizability	31.18 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

HMDB0038812

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018238

KNApSAcK ID

C00006956

Chemspider ID

9198142

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11022960

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4,4'-Dihydroxy-2',6'-dimethoxychalcone (NP0054659)

MOL for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

3D MOL for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

3D SDF for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

3D-SDF for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

PDB for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

3D PDB for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

SMILES for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

INCHI for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

Structure for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)

3D Structure for NP0054659 (4,4'-Dihydroxy-2',6'-dimethoxychalcone)