NP-MRD: Showing NP-Card for 2',3'-Dihydroxy-4',6'-dimethoxychalcone (NP0074915)

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Record Information

Version

2.0

Created at

2022-04-28 20:13:16 UTC

Updated at

2022-04-28 20:13:17 UTC

NP-MRD ID

NP0074915

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',3'-Dihydroxy-4',6'-dimethoxychalcone

Description

(2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, (2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one is considered to be a flavonoid lipid molecule (2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2',3'-Dihydroxy-4',6'-dimethoxychalcone is found in Anomianthus dulcis , Piper hispidum and Uvaria dulcis . It is generated by Dehydroxylase enzyme via a -4p-dehydroxylation-of-substituted-benzene reaction.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
   -5.7335   -1.0299   -0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1892    0.2627   -0.4943 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8516    0.5450   -0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9048   -0.4229   -0.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5483   -0.1132   -0.0855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -1.1561    0.0353 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0623   -2.4894    0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0968    1.1653   -0.0690 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2463    1.6284    0.0661 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3326    2.9645    0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    1.0938    0.2220 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0988   -0.0598    0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5418   -0.3374    0.4783 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9984   -1.6438    0.5626 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3240   -1.9181    0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2592   -0.9127    0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8455    0.3888    0.7115 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4754    0.6508    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1096    2.1421   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7228    3.4709   -0.1972 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4465    1.8645   -0.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4324    2.8324   -0.4778 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0395   -1.6640   -1.1441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7053   -1.0715   -1.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7800   -1.4357    0.5025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2261   -1.4580   -0.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2835   -2.8279   -1.0096 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1869   -3.0899    0.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9236   -2.7494    0.6595 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3627    1.9087    0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4843   -0.9252    0.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2342   -2.4202    0.4992 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6348   -2.9681    0.7764 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3186   -1.1837    0.9140 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5487    1.2070    0.7670 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1931    1.6996    0.4962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3146    4.2635   -0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1917    3.7888   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 12  2  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
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8 19  2  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
 18 13  1  0
  5  8  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 15 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
 20 37  1  0
 22 38  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
M  END

  Mrv1652308221907242D          

 24 25  0  0  0  0            999 V2000
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    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    0.0000    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
    5.7158    0.8250    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
    5.0013    2.0625    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
    7.1447    4.9500    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
    5.7158    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  9  8  2  0  0  0  0
 11  6  2  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14 10  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 17 15  2  0  0  0  0
 17 16  1  0  0  0  0
 18 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21  1  1  0  0  0  0
 21 13  1  0  0  0  0
 22  2  1  0  0  0  0
 22 14  1  0  0  0  0
 23  8  1  0  0  0  0
 24  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0074915

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C1=C(O)C(O)=C(OC)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O5/c1-21-13-10-14(22-2)16(19)17(20)15(13)12(18)9-8-11-6-4-3-5-7-11/h3-10,19-20H,1-2H3/b9-8+

> <INCHI_KEY>
IAYOHSHBLLHXFB-CMDGGOBGSA-N

> <FORMULA>
C17H16O5

> <MOLECULAR_WEIGHT>
300.31

> <EXACT_MASS>
300.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
31.372977364912334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.60

> <JCHEM_LOGP>
3.617852134333333

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.834305348962236

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.414496235376914

> <JCHEM_PKA_STRONGEST_BASIC>
-4.601677535349349

> <JCHEM_POLAR_SURFACE_AREA>
75.99000000000001

> <JCHEM_REFRACTIVITY>
83.7652

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.73e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-AUG-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-AUG-19         0                                  
HETATM    1  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      14.671   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      16.004   6.160   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   23  H   UNK     0       8.002   4.620   0.000  0.00  0.00           H+0
HETATM   24  H   UNK     0      12.003   3.850   0.000  0.00  0.00           H+0
CONECT    1   21                                                            
CONECT    2   22                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   11                                                       
CONECT    8    9   11   23                                                  
CONECT    9    8   12   24                                                  
CONECT   10   13   14                                                       
CONECT   11    6    7    8                                                  
CONECT   12    9   15   18                                                  
CONECT   13   10   15   21                                                  
CONECT   14   10   16   22                                                  
CONECT   15   12   13   17                                                  
CONECT   16   14   17   19                                                  
CONECT   17   15   16   20                                                  
CONECT   18   12                                                            
CONECT   19   16                                                            
CONECT   20   17                                                            
CONECT   21    1   13                                                       
CONECT   22    2   14                                                       
CONECT   23    8                                                            
CONECT   24    9                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₇H₁₆O₅

Average Mass

300.3100 Da

Monoisotopic Mass

300.09977 Da

IUPAC Name

(2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

Traditional Name

(2E)-1-(2,3-dihydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC=CC=C1)C(=O)C1=C(O)C(O)=C(OC)C=C1OC

InChI Identifier

InChI=1S/C17H16O5/c1-21-13-10-14(22-2)16(19)17(20)15(13)12(18)9-8-11-6-4-3-5-7-11/h3-10,19-20H,1-2H3/b9-8+

InChI Key

IAYOHSHBLLHXFB-CMDGGOBGSA-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
Anomianthus dulcis	Plant	KNApSAcK
Piper hispidum	LOTUS Database	35616633
Uvaria dulcis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone 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'-Hydroxychalcones

Alternative Parents

Substituents

2'-hydroxychalcone
Cinnamylphenol
Methoxyphenol
Dimethoxybenzene
M-dimethoxybenzene
4-alkoxyphenol
Benzoyl
Catechol
Phenol ether
Styrene
Phenoxy compound
Aryl ketone
Anisole
Methoxybenzene
Phenol
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Vinylogous acid
Enone
Ketone
Ether
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120338 )

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	3.6	ALOGPS
logP	3.62	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.41	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	31.37 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

HMDB0132911

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

22913738

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14159747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',3'-Dihydroxy-4',6'-dimethoxychalcone (NP0074915)

MOL for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

3D MOL for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

3D SDF for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

3D-SDF for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

PDB for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

3D PDB for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

SMILES for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

INCHI for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

Structure for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)

3D Structure for NP0074915 (2',3'-Dihydroxy-4',6'-dimethoxychalcone)