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Record Information
Version2.0
Created at2022-05-30 16:51:40 UTC
Updated at2022-05-30 16:51:40 UTC
NP-MRD IDNP0137410
Secondary Accession NumbersNone
Natural Product Identification
Common NameLicoflavanone
Description(S)-4',5,7-Trihydroxy-3'-prenylflavanone, also known as (2S)-abyssinone II or 3'-prenylnaringenin, belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position. Thus, (S)-4',5,7-trihydroxy-3'-prenylflavanone is considered to be a flavonoid lipid molecule (S)-4',5,7-Trihydroxy-3'-prenylflavanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (S)-4',5,7-Trihydroxy-3'-prenylflavanone has been detected, but not quantified in, herbs and spices and tea. Licoflavanone is found in Broussonetia papyrifera and Glycyrrhiza glabra. This could make (S)-4',5,7-trihydroxy-3'-prenylflavanone a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
(2S)-Abyssinone IIHMDB
(2S)-3'-(3,3-Dimethylallyl)-4',5,7-trihydroxyflavononeHMDB
3'-PrenylnaringeninHMDB
LicoflavanoneHMDB
Yinyanghuo DHMDB
Chemical FormulaC20H20O5
Average Mass340.3698 Da
Monoisotopic Mass340.13107 Da
IUPAC Name5,7-dihydroxy-2-[4-hydroxy-3-(3-methylbut-2-en-1-yl)phenyl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namelicoflavanone
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=CC(=CC=C1O)C1CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C20H20O5/c1-11(2)3-4-12-7-13(5-6-15(12)22)18-10-17(24)20-16(23)8-14(21)9-19(20)25-18/h3,5-9,18,21-23H,4,10H2,1-2H3
InChI KeyCGKWSLSAYABZTL-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Broussonetia papyriferaLOTUS Database
Glycyrrhiza glabraLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavanones. These are flavanones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct Parent3'-prenylated flavanones
Alternative Parents
Substituents
  • 3'-prenylated flavanone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Hydroxyflavonoid
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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
logP3.32ALOGPS
logP4.56ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.9ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity95.53 m³·mol⁻¹ChemAxon
Polarizability36.69 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029866
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001095
KNApSAcK IDC00008451
Chemspider ID22943308
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14218027
PDB IDNot Available
ChEBI ID565777
Good Scents IDNot Available
References
General ReferencesNot Available