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Record Information
Version1.0
Created at2022-05-31 17:54:51 UTC
Updated at2022-05-31 17:54:51 UTC
NP-MRD IDNP0138314
Secondary Accession NumbersNone
Natural Product Identification
Common Name2',6'-Dihydroxy 4'-methoxydihydrochalcone
Description1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone, also known as 2',6'-dihydroxy-4'-methoxydihydrochalcone, belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position. Thus, 1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone is considered to be a flavonoid lipid molecule. It was first documented in 1994 (PMID: 8158163). 1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenyl-1-propanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 17397884) (PMID: 21680165) (PMID: 22516933).
Structure
Thumb
Synonyms
ValueSource
1-(2,6-Dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-oneHMDB
2',6'-Dihydroxy-4'-methoxy-b-phenylpropiophenoneHMDB
2',6'-Dihydroxy-4'-methoxydihydrochalconeHMDB
2',6'-Dihydroxy-4'-methoxydihydrochaloneHMDB
2',6'-Dihydroxy-4'-methoxydihydro-chalconeHMDB
Chemical FormulaC16H16O4
Average Mass272.2958 Da
Monoisotopic Mass272.10486 Da
IUPAC Name1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one
Traditional Name1-(2,6-dihydroxy-4-methoxyphenyl)-3-phenylpropan-1-one
CAS Registry Number35241-55-5
SMILES
COC1=CC(O)=C(C(=O)CCC2=CC=CC=C2)C(O)=C1
InChI Identifier
InChI=1S/C16H16O4/c1-20-12-9-14(18)16(15(19)10-12)13(17)8-7-11-5-3-2-4-6-11/h2-6,9-10,18-19H,7-8H2,1H3
InChI KeyMDMCODCJMHTFIZ-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2'-hydroxy-dihydrochalcones. These are organic compounds containing dihydrochalcone skeleton that carries a hydroxyl group at the 2'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent2'-Hydroxy-dihydrochalcones
Alternative Parents
Substituents
  • 2'-hydroxy-dihydrochalcone
  • Cinnamylphenol
  • Alkyl-phenylketone
  • Butyrophenone
  • Methoxyphenol
  • Phenylketone
  • Anisole
  • Benzoyl
  • Phenoxy compound
  • Phenol ether
  • Resorcinol
  • Aryl ketone
  • Aryl alkyl ketone
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.28ALOGPS
logP4.34ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.88ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity76.21 m³·mol⁻¹ChemAxon
Polarizability28.91 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0034435
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012836
KNApSAcK IDC00007929
Chemspider ID148386
KEGG Compound IDC09644
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound169676
PDB IDNot Available
ChEBI ID28523
Good Scents IDNot Available
References
General References
  1. Portet B, Fabre N, Roumy V, Gornitzka H, Bourdy G, Chevalley S, Sauvain M, Valentin A, Moulis C: Activity-guided isolation of antiplasmodial dihydrochalcones and flavanones from Piper hostmannianum var. berbicense. Phytochemistry. 2007 May;68(9):1312-20. doi: 10.1016/j.phytochem.2007.02.006. Epub 2007 Mar 29. [PubMed:17397884 ]
  2. Mapunya MB, Hussein AA, Rodriguez B, Lall N: Tyrosinase activity of Greyia flanaganii (Bolus) constituents. Phytomedicine. 2011 Aug 15;18(11):1006-12. doi: 10.1016/j.phymed.2011.03.013. Epub 2011 Jun 15. [PubMed:21680165 ]
  3. Cabanillas BJ, Le Lamer AC, Castillo D, Arevalo J, Estevez Y, Rojas R, Valadeau C, Bourdy G, Sauvain M, Fabre N: Dihydrochalcones and benzoic acid derivatives from Piper dennisii. Planta Med. 2012 Jun;78(9):914-8. doi: 10.1055/s-0031-1298459. Epub 2012 Apr 19. [PubMed:22516933 ]
  4. Orjala J, Wright AD, Behrends H, Folkers G, Sticher O, Ruegger H, Rali T: Cytotoxic and antibacterial dihydrochalcones from Piper aduncum. J Nat Prod. 1994 Jan;57(1):18-26. doi: 10.1021/np50103a003. [PubMed:8158163 ]