NP-MRD: Showing NP-Card for methoxychalcone (NP0289265)

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Record Information

Version

2.0

Created at

2022-09-09 19:22:06 UTC

Updated at

2022-09-09 19:22:06 UTC

NP-MRD ID

NP0289265

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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. methoxychalcone is found in Ficus lyrata. methoxychalcone was first documented in 2021 (PMID: 34641514). Based on a literature review a small amount of articles have been published on 4-Methoxychalcone (PMID: 35961598) (PMID: 35955537) (PMID: 35717804) (PMID: 34780470).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -5.6502   -1.5081   -1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4396   -0.1722   -1.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1525    0.1963   -0.8071 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8585    1.4792   -0.3966 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5945    1.8548   -0.0277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5452    0.9363   -0.0558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2326    1.3744    0.3403 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8300    0.5873    0.3509 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1348    1.0787    0.7598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420    2.2776    1.1080 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171    0.2380    0.7811 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5504    0.7435    1.1788 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6608   -0.0340    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5924   -1.3690    0.8250 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3888   -1.8759    0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2427   -1.0822    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8165   -0.3395   -0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0980   -0.6916   -0.8257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2764   -2.2393   -0.8125 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0763   -1.7438   -2.5110 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7259   -1.7211   -1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7057    2.1812   -0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4085    2.8915    0.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404    2.4144    0.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6936   -0.4386    0.0435 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5735    1.7978    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6256    0.3862    1.5198 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5146   -1.9276    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3190   -2.9003    0.1403 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3249   -1.5597    0.0833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0548   -1.1082   -0.5076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3345   -1.7165   -1.1541 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
  6 17  1  0
 17 18  2  0
 18  3  1  0
 16 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  7 24  1  0
  8 25  1  0
 12 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 18 32  1  0
M  END


  Mrv1652309092221222D          

 18 19  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
    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
    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
    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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 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
 11 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
  3 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0289265

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
XUFXKBJMCRJATM-FMIVXFBMSA-N

> <FORMULA>
C16H14O2

> <MOLECULAR_WEIGHT>
238.286

> <EXACT_MASS>
238.099379691

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.86569210390116

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
3.7326540433333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.080510672778797

> <JCHEM_PKA_STRONGEST_BASIC>
-4.822152377641354

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
73.34020000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         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  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335 -12.320   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   18  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   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    6   18                                                       
CONECT   18   17    3                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₂

Average Mass

238.2860 Da

Monoisotopic Mass

238.09938 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

XUFXKBJMCRJATM-FMIVXFBMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Ficus lyrata	LOTUS Database	35616633

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

Not Available

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	3.73	ChemAxon
pKa (Strongest Acidic)	17.08	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00006930

Chemspider ID

557051

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chalconoid

METLIN ID

Not Available

PubChem Compound

641819

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dej-Adisai S, Rais IR, Wattanapiromsakul C, Pitakbut T: Alpha-Glucosidase Inhibitory Assay-Screened Isolation and Molecular Docking Model from Bauhinia pulla Active Compounds. Molecules. 2021 Oct 1;26(19). pii: molecules26195970. doi: 10.3390/molecules26195970. [PubMed:34641514 ]
Raju R, Gunawardena D, Reddell P, Munch G: Cryptocaryoic acids A - C: New phenyl alkyl acids isolated from the leaves of Australian rainforest plant Cryptocarya mackinnoniana. Fitoterapia. 2022 Oct;162:105266. doi: 10.1016/j.fitote.2022.105266. Epub 2022 Aug 10. [PubMed:35961598 ]
Zheng K, Liu M, Meng Z, Xiao Z, Zhong F, Wang W, Qin C: Copper Foam as Active Catalysts for the Borylation of alpha, beta-Unsaturated Compounds. Int J Mol Sci. 2022 Jul 29;23(15):8403. doi: 10.3390/ijms23158403. [PubMed:35955537 ]
Del Rosario H, Saavedra E, Brouard I, Gonzalez-Santana D, Garcia C, Spinola-Lasso E, Tabraue C, Quintana J, Estevez F: Structure-activity relationships reveal a 2-furoyloxychalcone as a potent cytotoxic and apoptosis inducer for human U-937 and HL-60 leukaemia cells. Bioorg Chem. 2022 Oct;127:105926. doi: 10.1016/j.bioorg.2022.105926. Epub 2022 Jun 11. [PubMed:35717804 ]
Escrivani DO, Charlton RL, Caruso MB, Burle-Caldas GA, Borsodi MPG, Zingali RB, Arruda-Costa N, Palmeira-Mello MV, de Jesus JB, Souza AMT, Abrahim-Vieira B, Freitag-Pohl S, Pohl E, Denny PW, Rossi-Bergmann B, Steel PG: Chalcones identify cTXNPx as a potential antileishmanial drug target. PLoS Negl Trop Dis. 2021 Nov 15;15(11):e0009951. doi: 10.1371/journal.pntd.0009951. eCollection 2021 Nov. [PubMed:34780470 ]
LOTUS database [Link]

Showing NP-Card for methoxychalcone (NP0289265)

MOL for NP0289265 (methoxychalcone)

3D MOL for NP0289265 (methoxychalcone)

3D SDF for NP0289265 (methoxychalcone)

3D-SDF for NP0289265 (methoxychalcone)

PDB for NP0289265 (methoxychalcone)

3D PDB for NP0289265 (methoxychalcone)

SMILES for NP0289265 (methoxychalcone)

INCHI for NP0289265 (methoxychalcone)

Structure for NP0289265 (methoxychalcone)

3D Structure for NP0289265 (methoxychalcone)