NP-MRD: Showing NP-Card for 4'-Hydroxy-2'-methoxychalcone (NP0054630)

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Record Information

Version

2.0

Created at

2022-04-28 00:55:23 UTC

Updated at

2022-04-28 00:55:23 UTC

NP-MRD ID

NP0054630

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-Hydroxy-2'-methoxychalcone

Description

4'-Hydroxy-2'-methoxychalcone 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'-hydroxy-2'-methoxychalcone is considered to be a flavonoid lipid molecule. 4'-Hydroxy-2'-methoxychalcone is found in Acacia neovernicosa, Amorpha fruticosa, Dalbergia cochinchinensis and Oxytropis falcata. 4'-Hydroxy-2'-methoxychalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
   -4.2610   -2.6721   -0.1295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0708   -1.9496   -0.1038 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9564   -0.6024    0.0925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0292    0.2220    0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8908    1.5768    0.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0065    2.3935    0.6913 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6489    2.1428    0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358    1.3177    0.2837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6455   -0.0374    0.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5273   -0.9055   -0.1245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8519   -2.1769   -0.2945 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8673   -0.6950   -0.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6542    0.3375   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1045    0.2466   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8767    1.4079   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2450    1.4123   -0.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9397    0.2489   -0.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2128   -0.9068   -0.5291 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8142   -0.8990   -0.4294 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7699   -2.7402    0.8518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9348   -2.2886   -0.9341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0005   -3.7243   -0.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0474   -0.1757    0.3045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3335    2.5463    1.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5200    3.1990    0.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6157    1.8551    0.3004 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4400   -1.6717   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2697    1.3075    0.0847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    2.3441    0.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8024    2.3249   -0.0802 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0387    0.2449   -0.4830 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7360   -1.8452   -0.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2964   -1.8373   -0.5353 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 12 10  1  0
 10 11  2  0
 10  9  1  0
  9  3  2  0
  3  2  1  0
  2  1  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
 19 14  1  0
  8  9  1  0
 12 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
M  END


  Mrv1652310051715262D          

 21 22  0  0  0  0            999 V2000
    6.4302    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    0.0000    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
    7.1447    4.9500    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
    5.7158    2.4750    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
    5.0013    1.2375    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
    5.7158    3.3000    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
    8.5737    4.9500    0.0000 O   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
    7.1447    2.4750    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    2.8875    0.0000 H   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
  9  8  2  0  0  0  0
 10  7  2  0  0  0  0
 12  5  2  0  0  0  0
 12  6  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16 11  1  0  0  0  0
 16 14  2  0  0  0  0
 17 13  1  0  0  0  0
 18 15  2  0  0  0  0
 19  1  1  0  0  0  0
 19 16  1  0  0  0  0
 20  7  1  0  0  0  0
 21 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0054630

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O3/c1-19-16-11-13(17)8-9-14(16)15(18)10-7-12-5-3-2-4-6-12/h2-11,17H,1H3/b10-7+

> <INCHI_KEY>
VLEOOBKBMSIDKF-JXMROGBWSA-N

> <FORMULA>
C16H14O3

> <MOLECULAR_WEIGHT>
254.285

> <EXACT_MASS>
254.094294311

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
27.59116591919734

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.91

> <JCHEM_LOGP>
3.4290887216666666

> <ALOGPS_LOGS>
-4.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.053492531089113

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.926763311224197

> <JCHEM_PKA_STRONGEST_BASIC>
-4.88544251040455

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
75.3211

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-OCT-17         0                                  
HETATM    1  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      14.670   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.003   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669   6.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      16.004   9.240   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336   6.930   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337   4.620   0.000  0.00  0.00           O+0
HETATM   20  H   UNK     0       8.002   4.620   0.000  0.00  0.00           H+0
HETATM   21  H   UNK     0      12.003   5.390   0.000  0.00  0.00           H+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   12                                                       
CONECT    6    4   12                                                       
CONECT    7   10   12   20                                                  
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10    7   15   21                                                  
CONECT   11   13   16                                                       
CONECT   12    5    6    7                                                  
CONECT   13    8   11   17                                                  
CONECT   14    9   15   16                                                  
CONECT   15   10   14   18                                                  
CONECT   16   11   14   19                                                  
CONECT   17   13                                                            
CONECT   18   15                                                            
CONECT   19    1   16                                                       
CONECT   20    7                                                            
CONECT   21   10                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-Methoxyisoliquiritigenin	ChEMBL

Chemical Formula

C₁₆H₁₄O₃

Average Mass

254.2850 Da

Monoisotopic Mass

254.09429 Da

IUPAC Name

(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one

Traditional Name

(2E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C16H14O3/c1-19-16-11-13(17)8-9-14(16)15(18)10-7-12-5-3-2-4-6-12/h2-11,17H,1H3/b10-7+

InChI Key

VLEOOBKBMSIDKF-JXMROGBWSA-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
Acacia neovernicosa	Plant	KNApSAcK
Amorpha fruticosa	LOTUS Database	35616633
Dalbergia cochinchinensis	Plant	KNApSAcK
Oxytropis falcata	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
Cinnamic acid or derivatives
Methoxyphenol
Anisole
Benzoyl
Phenoxy compound
Phenol ether
Styrene
Aryl ketone
Methoxybenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Enone
Alpha,beta-unsaturated ketone
Acryloyl-group
Ketone
Ether
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120017 )

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	3.91	ALOGPS
logP	3.43	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	7.93	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	75.32 m³·mol⁻¹	ChemAxon
Polarizability	27.59 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

HMDB0151881

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

13842401

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4'-Hydroxy-2'-methoxychalcone (NP0054630)

MOL for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

3D MOL for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

3D SDF for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

3D-SDF for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

PDB for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

3D PDB for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

SMILES for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

INCHI for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

Structure for NP0054630 (4'-Hydroxy-2'-methoxychalcone)

3D Structure for NP0054630 (4'-Hydroxy-2'-methoxychalcone)