NP-MRD: Showing NP-Card for 4'-Methoxychalcone (NP0047411)

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Record Information

Version

2.0

Created at

2022-03-17 20:39:46 UTC

Updated at

2022-03-17 20:39:46 UTC

NP-MRD ID

NP0047411

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4'-Methoxychalcone

Description

4'-Methoxychalcone belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones that are structurally distinguished by the lack of oxygen functionalities at the C2'- and C6'-positions. Thus, 4'-methoxychalcone is considered to be a flavonoid lipid molecule. 4'-Methoxychalcone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 4'-Methoxychalcone has been detected, but not quantified in, citrus and lemons. This could make 4'-methoxychalcone a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306342D          

 18 19  0  0  0  0            999 V2000
    0.0000    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    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
   -2.8579    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
   -3.5724    2.0625    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
   -2.1434    4.5375    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
   -1.4289    4.9500    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    1.2375    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
   -2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    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
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  7  2  0  0  0  0
 13  5  2  0  0  0  0
 13  6  1  0  0  0  0
 13  7  1  0  0  0  0
 14  8  2  0  0  0  0
 14  9  1  0  0  0  0
 15 10  2  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 16  2  0  0  0  0
 18  1  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047411

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O2/c1-18-15-10-8-14(9-11-15)16(17)12-7-13-5-3-2-4-6-13/h2-12H,1H3/b12-7+

> <INCHI_KEY>
KJHHAPASNNVTSN-KPKJPENVSA-N

> <FORMULA>
C16H14O2

> <MOLECULAR_WEIGHT>
238.2812

> <EXACT_MASS>
238.099379692

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.86628381697294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.53

> <JCHEM_LOGP>
3.7326540433333335

> <ALOGPS_LOGS>
-4.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.089095574691807

> <JCHEM_PKA_STRONGEST_BASIC>
-4.837271947532323

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
73.3402

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.53e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

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       0.000  10.780   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   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      -5.335   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      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   6.930   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      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.668   6.930   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000   9.240   0.000  0.00  0.00           O+0
CONECT    1   18                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3   13                                                       
CONECT    6    4   13                                                       
CONECT    7   12   13                                                       
CONECT    8   10   14                                                       
CONECT    9   11   14                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    7   16                                                       
CONECT   13    5    6    7                                                  
CONECT   14    8    9   16                                                  
CONECT   15   10   11   18                                                  
CONECT   16   12   14   17                                                  
CONECT   17   16                                                            
CONECT   18    1   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
4,4'-Dimethoxy-benzophenone	HMDB
4,4'-Dimethoxybenzophenone	HMDB
Bis(4-methoxyphenyl)-methanone	HMDB
Bis(4-methoxyphenyl)methanone	HMDB
Bis(p-methoxy)benzophenone	HMDB
p,P'-dimethoxybenzophenone	HMDB
4'-Methoxychalcone, (e)-isomer	HMDB
4'-Methoxychalcone, (Z)-isomer	HMDB
4'-Methoxychalcone	MeSH

Chemical Formula

C₁₆H₁₄O₂

Average Mass

238.2812 Da

Monoisotopic Mass

238.09938 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

22966-19-4

SMILES

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

InChI Identifier

InChI=1S/C16H14O2/c1-18-15-10-8-14(9-11-15)16(17)12-7-13-5-3-2-4-6-13/h2-12H,1H3/b12-7+

InChI Key

KJHHAPASNNVTSN-KPKJPENVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Citrus limon	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as retrochalcones. These are a form of normal chalcones 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

Retrochalcones

Alternative Parents

Substituents

Retrochalcone
Anisole
Benzoyl
Phenol ether
Styrene
Phenoxy compound
Aryl ketone
Methoxybenzene
Alkyl aryl ether
Monocyclic benzene moiety
Benzenoid
Acryloyl-group
Alpha,beta-unsaturated ketone
Enone
Ketone
Ether
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Chalcones and dihydrochalcones (LMPK12120188 )

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	3.53	ALOGPS
logP	3.73	ChemAxon
logS	-4.7	ALOGPS
pKa (Strongest Acidic)	17.09	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73.34 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032585

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010522

KNApSAcK ID

C00006917

Chemspider ID

557050

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

641818

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4'-Methoxychalcone (NP0047411)

MOL for NP0047411 (4'-Methoxychalcone)

3D MOL for NP0047411 (4'-Methoxychalcone)

3D SDF for NP0047411 (4'-Methoxychalcone)

3D-SDF for NP0047411 (4'-Methoxychalcone)

PDB for NP0047411 (4'-Methoxychalcone)

3D PDB for NP0047411 (4'-Methoxychalcone)

SMILES for NP0047411 (4'-Methoxychalcone)

INCHI for NP0047411 (4'-Methoxychalcone)

Structure for NP0047411 (4'-Methoxychalcone)

3D Structure for NP0047411 (4'-Methoxychalcone)