NP-MRD: Showing NP-Card for 2',6'-Dihydroxy-4'-methoxychalcone (NP0054641)

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Record Information

Version

2.0

Created at

2022-04-28 00:55:50 UTC

Updated at

2022-04-28 00:55:50 UTC

NP-MRD ID

NP0054641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2',6'-Dihydroxy-4'-methoxychalcone

Description

Pinostrobin chalcone 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, pinostrobin chalcone is considered to be a flavonoid lipid molecule. Pinostrobin chalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Pinostrobin chalcone has been detected, but not quantified in, pulses. 2',6'-Dihydroxy-4'-methoxychalcone is found in Alpinia mutica, Alpinia pricei, Boesenbergia pandurata , Boesenbergia rotunda, Boesenbergia rotunda (L.) Mansf.Kulturpfl. , Cajanus cajan , Helichrysum cymosum, Helichrysum spp., Lindera umbellata , Onychium siliculosum, Pinus clausa, Piper aduncum , Piper hispidum , Pityrogramma chrysophylla , Pityrogramma ebenea, Pityrogramma tartarea, Populus cathayana, Populus laurifolia, Populus maximowiczii, Populus spp. and Woodsia scopulina. This could make pinostrobin chalcone a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -5.8878    0.9430    1.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5480   -0.2208    0.5530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1978   -0.4502    0.2936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2106    0.4018    0.7174 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8580    0.1644    0.4530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9573    1.0985    0.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4719   -0.9367   -0.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0847   -1.2056   -0.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2321   -2.2601   -1.1931 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668   -0.3751   -0.1343 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2997   -0.7325   -0.4601 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4371    0.0803   -0.0734 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149   -0.3689   -0.4584 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8722    0.3034   -0.1580 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8282    1.4853    0.5569 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5872    1.9255    0.9332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4058    1.2436    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4409   -1.8290   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2066   -2.9531   -1.3909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7912   -1.5542   -0.4069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2568    0.9335    2.2202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5905    1.8293    0.7204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9426    0.9353    1.6160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4850    1.2747    1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2361    1.9189    1.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9940    0.5368    0.4208 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4381   -1.6635   -1.0326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7687   -1.3009   -1.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8488   -0.0528   -0.4600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7477    2.0024    0.7853 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5037    2.8367    1.4888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4507    1.6354    0.9507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4623   -3.4152   -1.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5674   -2.2303   -0.7439 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  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
  7 18  1  0
 18 19  1  0
 18 20  2  0
 20  3  1  0
 17 12  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
  6 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 14 29  1  0
 15 30  1  0
 16 31  1  0
 17 32  1  0
 19 33  1  0
 20 34  1  0
M  END

  Mrv0541 05061307182D          

 20 21  0  0  0  0            999 V2000
    2.1434    9.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    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
   -0.7145    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
   -1.4289    5.7750    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
    1.4289    7.4250    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
   -1.4289    4.9500    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
   -0.7145    7.0125    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
    0.0000    8.2500    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
   -1.4289    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
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  6  4  2  0  0  0  0
  8  7  2  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 11  7  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 16 13  1  0  0  0  0
 16 14  2  0  0  0  0
 16 15  1  0  0  0  0
 17 13  2  0  0  0  0
 18 14  1  0  0  0  0
 19 15  1  0  0  0  0
 20  1  1  0  0  0  0
 20 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054641

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O4/c1-20-12-9-14(18)16(15(19)10-12)13(17)8-7-11-5-3-2-4-6-11/h2-10,18-19H,1H3/b8-7+

> <INCHI_KEY>
CUGDOWNTXKLQMD-BQYQJAHWSA-N

> <FORMULA>
C16H14O4

> <MOLECULAR_WEIGHT>
270.28

> <EXACT_MASS>
270.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
28.556914902277914

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.64

> <JCHEM_LOGP>
4.425523399999999

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.263321926381863

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.958058804872606

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857665581494396

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
77.30199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylprop-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       4.001  17.710   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   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      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  13.860   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  16.170   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  15.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  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       0.000  13.860   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -2.667  13.860   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.334  11.550   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334  16.170   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.001  16.170   0.000  0.00  0.00           O+0
CONECT    1   20                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   11                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   12   14                                                       
CONECT   10   12   15                                                       
CONECT   11    5    6    7                                                  
CONECT   12    9   10   20                                                  
CONECT   13    8   16   17                                                  
CONECT   14    9   16   18                                                  
CONECT   15   10   16   19                                                  
CONECT   16   13   14   15                                                  
CONECT   17   13                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20    1   12                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
2',6'-Dihydroxy-4'-methoxychalcone	HMDB

Chemical Formula

C₁₆H₁₄O₄

Average Mass

270.2800 Da

Monoisotopic Mass

270.08921 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H14O4/c1-20-12-9-14(18)16(15(19)10-12)13(17)8-7-11-5-3-2-4-6-11/h2-10,18-19H,1H3/b8-7+

InChI Key

CUGDOWNTXKLQMD-BQYQJAHWSA-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 mutica	LOTUS Database	35616633
Alpinia pricei	LOTUS Database	35616633
Boesenbergia pandurata	Plant	KNApSAcK
Boesenbergia rotunda	LOTUS Database	35616633
Boesenbergia rotunda (L.) Mansf.Kulturpfl.	Plant	KNApSAcK
Cajanus cajan	Plant	KNApSAcK
Helichrysum cymosum	LOTUS Database	35616633
Helichrysum spp.	Plant	KNApSAcK
Lindera umbellata	Plant	KNApSAcK
Onychium siliculosum	Plant	KNApSAcK
Pinus clausa	LOTUS Database	35616633
Piper aduncum	Plant	KNApSAcK
Piper hispidum	Plant	KNApSAcK
Pityrogramma chrysophylla	Plant	KNApSAcK
Pityrogramma ebenea	LOTUS Database	35616633
Pityrogramma tartarea	Plant	KNApSAcK
Populus cathayana	LOTUS Database	35616633
Populus laurifolia	LOTUS Database	35616633
Populus maximowiczii	LOTUS Database	35616633
Populus spp.	Plant	KNApSAcK
Woodsia scopulina	LOTUS Database	35616633

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120244 )

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	3.64	ALOGPS
logP	4.43	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.96	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.3 m³·mol⁻¹	ChemAxon
Polarizability	28.56 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

HMDB0033702

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011816

KNApSAcK ID

C00006934

Chemspider ID

4475770

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5316793

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 2',6'-Dihydroxy-4'-methoxychalcone (NP0054641)

MOL for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

3D MOL for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

3D SDF for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

3D-SDF for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

PDB for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

3D PDB for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

SMILES for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

INCHI for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

Structure for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)

3D Structure for NP0054641 (2',6'-Dihydroxy-4'-methoxychalcone)