NP-MRD: Showing NP-Card for Chalcone (NP0001314)

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Record Information

Version

1.0

Created at

2006-05-22 15:12:30 UTC

Updated at

2024-04-19 09:28:04 UTC

NP-MRD ID

NP0001314

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Chalcone

Description

Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones. They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst. This reaction has been found to work in without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education. In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 degree centigrade).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900052D          

 16 17  0  0  0  0            999 V2000
   14.1635  -11.0138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5926  -11.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1635  -13.4888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8781  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1635  -12.6638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8781  -12.2512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5926  -10.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3070  -11.4262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8781  -13.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4491  -13.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3070   -9.7763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0214  -11.0138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8781  -14.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4491  -14.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0214  -10.1888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1635  -15.1388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0  0  0  0
  2  4  1  0  0  0  0
  2  7  2  0  0  0  0
  2  8  1  0  0  0  0
  3  5  1  0  0  0  0
  3  9  2  0  0  0  0
  3 10  1  0  0  0  0
  4  6  1  0  0  0  0
  5  6  2  0  0  0  0
  7 11  1  0  0  0  0
  8 12  2  0  0  0  0
  9 13  1  0  0  0  0
 10 14  2  0  0  0  0
 11 15  2  0  0  0  0
 12 15  1  0  0  0  0
 13 16  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001314

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+

> <INCHI_KEY>
DQFBYFPFKXHELB-VAWYXSNFSA-N

> <FORMULA>
C15H12O

> <MOLECULAR_WEIGHT>
208.2552

> <EXACT_MASS>
208.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
23.7249476012255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1,3-diphenylprop-2-en-1-one

> <ALOGPS_LOGP>
3.63

> <JCHEM_LOGP>
3.8903253089999996

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.908574825151867

> <JCHEM_PKA_STRONGEST_BASIC>
-7.303976722038771

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.87700000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trans-chalcone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      26.439 -20.559   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      29.106 -20.559   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.439 -25.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      27.772 -21.329   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      26.439 -23.639   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.772 -22.869   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.106 -19.019   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.440 -21.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.772 -25.949   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.105 -25.949   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.440 -18.249   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      31.773 -20.559   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.772 -27.489   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.105 -27.489   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.773 -19.019   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.439 -28.259   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    4    7    8                                                  
CONECT    3    5    9   10                                                  
CONECT    4    1    2    6                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    2   11                                                       
CONECT    8    2   12                                                       
CONECT    9    3   13                                                       
CONECT   10    3   14                                                       
CONECT   11    7   15                                                       
CONECT   12    8   15                                                       
CONECT   13    9   16                                                       
CONECT   14   10   16                                                       
CONECT   15   11   12                                                       
CONECT   16   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0003066
HETATM    1  O1  UNL     1      -1.096   2.383  -0.386  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.172   1.154  -0.166  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.040   0.385  -0.069  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.206   0.966  -0.211  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.473   0.263  -0.129  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.590  -1.085   0.106  1.00  0.00           C  
HETATM    7  C6  UNL     1       3.815  -1.754   0.184  1.00  0.00           C  
HETATM    8  C7  UNL     1       4.941  -0.978   0.009  1.00  0.00           C  
HETATM    9  C8  UNL     1       4.846   0.377  -0.227  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.628   1.011  -0.299  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.468   0.543  -0.014  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.606  -0.797   0.228  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.872  -1.379   0.373  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.958  -0.550   0.262  1.00  0.00           C  
HETATM   15  C14 UNL     1      -4.827   0.789   0.020  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.590   1.329  -0.116  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.001  -0.665   0.118  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.207   2.026  -0.399  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.713  -1.685   0.242  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.863  -2.822   0.372  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.905  -1.486   0.067  1.00  0.00           H  
HETATM   22  H6  UNL     1       5.728   0.989  -0.365  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.577   2.095  -0.490  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.781  -1.488   0.323  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.951  -2.436   0.562  1.00  0.00           H  
HETATM   26  H10 UNL     1      -5.954  -1.001   0.375  1.00  0.00           H  
HETATM   27  H11 UNL     1      -5.742   1.405  -0.058  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.512   2.413  -0.311  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4    4   17
CONECT    4    5   18
CONECT    5    6    6   10
CONECT    6    7   19
CONECT    7    8    8   20
CONECT    8    9   21
CONECT    9   10   10   22
CONECT   10   23
CONECT   11   12   12   16
CONECT   12   13   24
CONECT   13   14   14   25
CONECT   14   15   26
CONECT   15   16   16   27
CONECT   16   28
END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2E)-1,3-Diphenyl-2-propen-1-one	ChEBI
(e)-1,3-Diphenyl-2-propen-1-one	ChEBI
(e)-Benzylideneacetophenone	ChEBI
(e)-Chalcone	ChEBI
1,3-Diphenyl-2-propen-1-one	ChEBI
Benzylideneacetophenone	ChEBI
Phenyl (e)--2-phenylethenyl ketone	ChEBI
Phenyl trans-styryl ketone	ChEBI
trans-Benzalacetophenone	ChEBI
trans-Benzylideneacetophenone	ChEBI
1, 3-Diphenyl-1-propen-3-one	HMDB
1,3-Diphenyl-2-propenone	HMDB
1,3-Diphenylpropenone	HMDB
1-Benzoyl-1-phenylethene	HMDB
1-Benzoyl-2-phenylethene	HMDB
1-Benzoyl-2-phenylethylene	HMDB
1-Phenyl-2-benzoylethylene	HMDB
2-Benzalacetophenone	HMDB
2-Benzylideneacetophenone	HMDB
3-Phenyl-acrylophenone	HMDB
3-Phenylacrylophenone	HMDB
a-Benzylideneacetophenone	HMDB
alpha-Benzylideneacetophenone	HMDB
b-Benzoylstyrene	HMDB
b-Phenylacrylophenone	HMDB
Benzalacetophenone	HMDB
Benzylidenecetophenone	HMDB
beta-Benzoylstyrene	HMDB
beta-Phenylacrylophenone	HMDB
Chalcone (acd/name 4.0)	HMDB
Chalkone	HMDB
Cinnamophenone	HMDB
Phenyl 2-phenylvinyl ketone	HMDB
Phenyl styryl ketone	HMDB
Styryl phenyl ketone	HMDB
1,3 Diphenyl 2 propen 1 one	HMDB
Chalcone	MeSH

Chemical Formula

C₁₅H₁₂O

Average Mass

208.2552 Da

Monoisotopic Mass

208.08882 Da

IUPAC Name

(2E)-1,3-diphenylprop-2-en-1-one

Traditional Name

trans-chalcone

CAS Registry Number

94-41-7

SMILES

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

InChI Identifier

InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H/b12-11+

InChI Key

DQFBYFPFKXHELB-VAWYXSNFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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	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, 176 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, 201 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
1D NMR	¹³C NMR Spectrum (1D, 226 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
Glycine max	KNApSAcK Database	22123792
Piper colonense	KNApSAcK Database	22123792
Piper hispidum	KNApSAcK Database	22123792
Piper sancti-feliz	KNApSAcK Database	22123792
Piper umbricola	KNApSAcK Database	22123792
Sophora flavescens	KNApSAcK Database	22123792
Sophora japonica	KNApSAcK Database	22123792
Taxus chinensis	KNApSAcK Database	22123792
Tilia tomentosa	LOTUS Database	35616633
Xanthorrhoea latifolia	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
Aryl ketone
Styrene
Benzoyl
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

chalcone (CHEBI:48965 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	57.5 °C	Not Available
Boiling Point	346.50 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	92.93 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.018	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0062 g/L	ALOGPS
logP	3.63	ALOGPS
logP	3.89	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	16.91	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	66.88 m³·mol⁻¹	ChemAxon
Polarizability	23.72 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

HMDB0003066

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Chalcone

METLIN ID

3342

PubChem Compound

637760

PDB ID

Not Available

ChEBI ID

48965

Good Scents ID

rw1414721

References

General References

Hawkins DR, Chasseaud LF, Weston KT: Aspects of the metabolism of the peripheral vasodilator mecinarone (14C-6809 MD) in rat, dog and man. Eur J Drug Metab Pharmacokinet. 1980;5(3):145-52. [PubMed:7202432 ]
Najafian M, Ebrahim-Habibi A, Hezareh N, Yaghmaei P, Parivar K, Larijani B: Trans-chalcone: a novel small molecule inhibitor of mammalian alpha-amylase. Mol Biol Rep. 2011 Mar;38(3):1617-20. doi: 10.1007/s11033-010-0271-3. Epub 2010 Sep 21. [PubMed:20857221 ]
Diaz-Tielas C, Grana E, Sotelo T, Reigosa MJ, Sanchez-Moreiras AM: The natural compound trans-chalcone induces programmed cell death in Arabidopsis thaliana roots. Plant Cell Environ. 2012 Aug;35(8):1500-17. doi: 10.1111/j.1365-3040.2012.02506.x. Epub 2012 Apr 22. [PubMed:22428920 ]
Bitencourt TA, Komoto TT, Massaroto BG, Miranda CE, Beleboni RO, Marins M, Fachin AL: Trans-chalcone and quercetin down-regulate fatty acid synthase gene expression and reduce ergosterol content in the human pathogenic dermatophyte Trichophyton rubrum. BMC Complement Altern Med. 2013 Sep 17;13:229. doi: 10.1186/1472-6882-13-229. [PubMed:24044691 ]
Xue X, Deng Y, Wang J, Zhou M, Liao L, Wang C, Peng C, Li Y: Hydroxysafflor yellow A, a natural compound from Carthamus tinctorius L with good effect of alleviating atherosclerosis. Phytomedicine. 2021 Aug 4;91:153694. doi: 10.1016/j.phymed.2021.153694. [PubMed:34403879 ]
Mathew B, Herrera-Acevedo C, Dev S, Rangarajan TM, Kuruniyan MS, Poonkuzhi NP, Scotti L, Scotti MT: Development of 2D, 3D-QSAR and Pharmacophore Modeling of Chalcones for the Inhibition of Monoamine Oxidase B. Comb Chem High Throughput Screen. 2021 Aug 16. pii: CCHTS-EPUB-117384. doi: 10.2174/1386207324666210816125738. [PubMed:34397324 ]
Bonvicini F, Belluti F, Bisi A, Gobbi S, Manet I, Gentilomi GA: Improved eradication efficacy of a combination of newly identified antimicrobial agents in C. albicans and S. aureus mixed-species biofilm. Res Microbiol. 2021 Aug 10:103873. doi: 10.1016/j.resmic.2021.103873. [PubMed:34389439 ]

Showing NP-Card for Chalcone (NP0001314)

MOL for NP0001314 (Chalcone)

3D MOL for NP0001314 (Chalcone)

3D SDF for NP0001314 (Chalcone)

3D-SDF for NP0001314 (Chalcone)

PDB for NP0001314 (Chalcone)

3D PDB for NP0001314 (Chalcone)

SMILES for NP0001314 (Chalcone)

INCHI for NP0001314 (Chalcone)

Structure for NP0001314 (Chalcone)

3D Structure for NP0001314 (Chalcone)