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Record Information
Version2.0
Created at2022-09-12 14:05:44 UTC
Updated at2022-09-12 14:05:44 UTC
NP-MRD IDNP0329577
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-[4-hydroxy-2-methoxy-5-(3-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Description864232-34-8 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. 3-[4-hydroxy-2-methoxy-5-(3-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one is found in Glycyrrhiza inflata. 864232-34-8 Is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC21H22O4
Average Mass338.4030 Da
Monoisotopic Mass338.15181 Da
IUPAC Name3-[4-hydroxy-2-methoxy-5-(3-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
Traditional Name3-[4-hydroxy-2-methoxy-5-(3-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
CAS Registry NumberNot Available
SMILES
COC1=CC(O)=C(C=C1C=CC(=O)C1=CC=C(O)C=C1)C(C)C(C)=C
InChI Identifier
InChI=1S/C21H22O4/c1-13(2)14(3)18-11-16(21(25-4)12-20(18)24)7-10-19(23)15-5-8-17(22)9-6-15/h5-12,14,22,24H,1H2,2-4H3
InChI KeySWPKMTGYQGHLJS-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Glycyrrhiza inflataLOTUS 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
  • Cinnamylphenol
  • Hydroxycinnamic acid or derivatives
  • Cinnamic acid or derivatives
  • Methoxyphenol
  • Phenylpropane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Benzoyl
  • Aryl ketone
  • Styrene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Acryloyl-group
  • Alpha,beta-unsaturated ketone
  • Enone
  • Ketone
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP4.56ALOGPS
logP4.75ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)7.83ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.76 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity100.42 m³·mol⁻¹ChemAxon
Polarizability37.36 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 Compound75149161
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]