NP-MRD: Showing NP-Card for 2',6',beta-Trihydroxy-4'-methoxychalcone (NP0054695)

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Record Information

Version

2.0

Created at

2022-04-28 00:58:14 UTC

Updated at

2022-04-28 00:58:14 UTC

NP-MRD ID

NP0054695

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',6',beta-Trihydroxy-4'-methoxychalcone

Description

2',6',Beta-Trihydroxy-4'-methoxychalcone belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 2',6',beta-trihydroxy-4'-methoxychalcone is considered to be a flavonoid lipid molecule. 2',6',beta-Trihydroxy-4'-methoxychalcone is found in Populus nigra . 2',6',Beta-Trihydroxy-4'-methoxychalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
    6.3881    0.1694   -0.8210 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2538   -0.3985   -1.4494 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0144   -0.1322   -0.8853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8514    0.6462    0.2376 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.8955    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4614    1.6916    1.9235 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4732    0.3539    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735    0.6320    0.7793 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1102    1.3598    1.8208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0667    0.0997    0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2215    0.5351    1.0397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0865    1.2543    2.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5541    0.1102    0.6464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7353   -0.6804   -0.4709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974   -1.0688   -0.8230 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0984   -0.6873   -0.0845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9067    0.0964    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6598    0.5075    1.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6450   -0.4235   -0.9359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5085   -0.9711   -1.5349 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9040   -0.6792   -1.4880 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1700    1.2672   -0.6955 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5857   -0.2764    0.1607 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2422    0.0614   -1.5361 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7069    1.0779    0.7164 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2540    2.1001    2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526   -0.9937    0.1943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1500    0.4866   -0.8319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -0.9989   -1.0739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1194   -1.6923   -1.7076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0912   -1.0248   -0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7616    0.4064    1.6140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5281    1.1326    2.2936 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5958   -1.5455   -2.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9942   -1.2968   -2.3730 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  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  7 19  1  0
 19 20  1  0
 19 21  2  0
 21  3  1  0
 18 13  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  6 26  1  0
 10 27  1  0
 10 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 18 33  1  0
 20 34  1  0
 21 35  1  0
M  END

  Mrv1533004251506062D          

 21 22  0  0  0  0            999 V2000
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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   -2.8875    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
    4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    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
    3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    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
    2.8579   -6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    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   -7.8375    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
   -0.0000   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    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
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  3 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054695

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C(C(=O)CC(=O)C2=CC=CC=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O5/c1-21-11-7-13(18)16(14(19)8-11)15(20)9-12(17)10-5-3-2-4-6-10/h2-8,18-19H,9H2,1H3

> <INCHI_KEY>
GLBWMOHCXNPFLS-UHFFFAOYSA-N

> <FORMULA>
C16H14O5

> <MOLECULAR_WEIGHT>
286.283

> <EXACT_MASS>
286.084123551

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.82581432526492

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione

> <ALOGPS_LOGP>
2.95

> <JCHEM_LOGP>
3.712558920666666

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.900267950364537

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.67410718426592

> <JCHEM_PKA_STRONGEST_BASIC>
-4.663542694688911

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
77.04700000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.668  -5.390   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  O   UNK     0       8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   21                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13                                                       
CONECT   19    7   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    3                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2',6',b-Trihydroxy-4'-methoxychalcone	Generator
2',6',Β-trihydroxy-4'-methoxychalcone	Generator

Chemical Formula

C₁₆H₁₄O₅

Average Mass

286.2830 Da

Monoisotopic Mass

286.08412 Da

IUPAC Name

1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione

Traditional Name

1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C(C(=O)CC(=O)C2=CC=CC=C2)C(O)=C1

InChI Identifier

InChI=1S/C16H14O5/c1-21-11-7-13(18)16(14(19)8-11)15(20)9-12(17)10-5-3-2-4-6-10/h2-8,18-19H,9H2,1H3

InChI Key

GLBWMOHCXNPFLS-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
Populus nigra	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retro-dihydrochalcones. These are a form of normal dihydrochalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Linear 1,3-diarylpropanoids

Sub Class

Chalcones and dihydrochalcones

Direct Parent

Retro-dihydrochalcones

Alternative Parents

Substituents

2'-hydroxy-dihydrochalcone
Retro-dihydrochalcone
Cinnamylphenol
Alkyl-phenylketone
Butyrophenone
Methoxyphenol
Phenylketone
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Resorcinol
Aryl ketone
Aryl alkyl ketone
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
1,3-diketone
1,3-dicarbonyl compound
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120398 )

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	2.95	ALOGPS
logP	3.71	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	8.67	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	77.05 m³·mol⁻¹	ChemAxon
Polarizability	28.83 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

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

42607650

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',6',beta-Trihydroxy-4'-methoxychalcone (NP0054695)

MOL for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

3D MOL for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

3D SDF for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

3D-SDF for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

PDB for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

3D PDB for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

SMILES for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

INCHI for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

Structure for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)

3D Structure for NP0054695 (2',6',beta-Trihydroxy-4'-methoxychalcone)