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Record Information
Version1.0
Created at2006-05-22 15:12:30 UTC
Updated at2021-08-19 23:59:01 UTC
NP-MRD IDNP0001314
Secondary Accession NumbersNone
Natural Product Identification
Common NameChalcone
DescriptionChalcone 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
Thumb
Synonyms
ValueSource
(2E)-1,3-Diphenyl-2-propen-1-oneChEBI
(e)-1,3-Diphenyl-2-propen-1-oneChEBI
(e)-BenzylideneacetophenoneChEBI
(e)-ChalconeChEBI
1,3-Diphenyl-2-propen-1-oneChEBI
BenzylideneacetophenoneChEBI
Phenyl (e)--2-phenylethenyl ketoneChEBI
Phenyl trans-styryl ketoneChEBI
trans-BenzalacetophenoneChEBI
trans-BenzylideneacetophenoneChEBI
1, 3-Diphenyl-1-propen-3-oneHMDB
1,3-Diphenyl-2-propenoneHMDB
1,3-DiphenylpropenoneHMDB
1-Benzoyl-1-phenyletheneHMDB
1-Benzoyl-2-phenyletheneHMDB
1-Benzoyl-2-phenylethyleneHMDB
1-Phenyl-2-benzoylethyleneHMDB
2-BenzalacetophenoneHMDB
2-BenzylideneacetophenoneHMDB
3-Phenyl-acrylophenoneHMDB
3-PhenylacrylophenoneHMDB
a-BenzylideneacetophenoneHMDB
alpha-BenzylideneacetophenoneHMDB
b-BenzoylstyreneHMDB
b-PhenylacrylophenoneHMDB
BenzalacetophenoneHMDB
BenzylidenecetophenoneHMDB
beta-BenzoylstyreneHMDB
beta-PhenylacrylophenoneHMDB
Chalcone (acd/name 4.0)HMDB
ChalkoneHMDB
CinnamophenoneHMDB
Phenyl 2-phenylvinyl ketoneHMDB
Phenyl styryl ketoneHMDB
Styryl phenyl ketoneHMDB
1,3 Diphenyl 2 propen 1 oneHMDB
ChalconeMeSH
Chemical FormulaC15H12O
Average Mass208.2552 Da
Monoisotopic Mass208.08882 Da
IUPAC Name(2E)-1,3-diphenylprop-2-en-1-one
Traditional Nametrans-chalcone
CAS Registry Number94-41-7
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 KeyDQFBYFPFKXHELB-VAWYXSNFSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Glycine maxKNApSAcK Database
Piper colonenseKNApSAcK Database
Piper hispidumKNApSAcK Database
Piper sancti-felizKNApSAcK Database
Piper umbricolaKNApSAcK Database
Sophora flavescensKNApSAcK Database
Sophora japonicaKNApSAcK Database
Taxus chinensisKNApSAcK Database
Tilia tomentosaLOTUS Database
Xanthorrhoea latifoliaLOTUS Database
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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct ParentRetrochalcones
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point57.5 °CNot Available
Boiling Point346.50 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility92.93 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.018Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0062 g/LALOGPS
logP3.63ALOGPS
logP3.89ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)16.91ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity66.88 m³·mol⁻¹ChemAxon
Polarizability23.72 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0003066
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023102
KNApSAcK IDC00053160
Chemspider ID553346
KEGG Compound IDC15589
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChalcone
METLIN ID3342
PubChem Compound637760
PDB IDNot Available
ChEBI ID48965
Good Scents IDrw1414721
References
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]