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Record Information
Version2.0
Created at2022-09-04 21:34:54 UTC
Updated at2022-09-04 21:34:54 UTC
NP-MRD IDNP0202376
Secondary Accession NumbersNone
Natural Product Identification
Common Name6-{2,6-dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal
Description6-{2,6-Dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position. 6-{2,6-dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal is found in Angelica keiskei. 6-{2,6-Dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H22O5
Average Mass366.4130 Da
Monoisotopic Mass366.14672 Da
IUPAC Name6-{2,6-dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal
Traditional Name6-{2,6-dihydroxy-3-[3-(4-hydroxyphenyl)prop-2-enoyl]phenyl}-4-methylhex-4-enal
CAS Registry NumberNot Available
SMILES
CC(CCC=O)=CCC1=C(O)C=CC(C(=O)C=CC2=CC=C(O)C=C2)=C1O
InChI Identifier
InChI=1S/C22H22O5/c1-15(3-2-14-23)4-10-18-21(26)13-11-19(22(18)27)20(25)12-7-16-5-8-17(24)9-6-16/h4-9,11-14,24,26-27H,2-3,10H2,1H3
InChI KeySXDGLCCGJJGJRY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Angelica keiskeiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-prenylated chalcones. These are chalcones featuring a C5-isoprenoid unit at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassChalcones and dihydrochalcones
Direct Parent3-prenylated chalcones
Alternative Parents
Substituents
  • 3-prenylated chalcone
  • 2'-hydroxychalcone
  • Cinnamylphenol
  • Cinnamic acid or derivatives
  • Hydroxycinnamic acid or derivatives
  • Benzoyl
  • Resorcinol
  • Styrene
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Enone
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Vinylogous acid
  • Alpha-hydrogen aldehyde
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Carbonyl group
  • Aldehyde
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
logP4.05ALOGPS
logP4.77ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)6.93ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity107 m³·mol⁻¹ChemAxon
Polarizability40.33 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound85446880
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]