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Record Information
Version2.0
Created at2022-04-27 23:59:07 UTC
Updated at2022-04-27 23:59:07 UTC
NP-MRD IDNP0053268
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one
DescriptionUralenol belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position. Thus, uralenol is considered to be a flavonoid lipid molecule. Uralenol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Uralenol has been detected, but not quantified in, herbs and spices. 2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-one is found in Broussonetia papyrifera , Glycyrrhiza glabra and Glycyrrhiza uralensis . This could make uralenol a potential biomarker for the consumption of these foods.
Structure
Thumb
Synonyms
ValueSource
2-[3,4-Dihydroxy-5-(3-methyl-2-butenyl)phenyl]-3,5,7-trihydroxy-4H-1-benzopyran-4-oneHMDB
3',4',5,7-Tetrahydroxy-5'-prenylflavonolHMDB
3,5,7,3',4'-Pentahydroxy-5'-isoprenylflavoneHMDB
Chemical FormulaC20H18O7
Average Mass370.3527 Da
Monoisotopic Mass370.10525 Da
IUPAC Name2-[3,4-dihydroxy-5-(3-methylbut-2-en-1-yl)phenyl]-3,5,7-trihydroxy-4H-chromen-4-one
Traditional Nameuralenol
CAS Registry NumberNot Available
SMILES
CC(C)=CCC1=CC(=CC(O)=C1O)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C20H18O7/c1-9(2)3-4-10-5-11(6-14(23)17(10)24)20-19(26)18(25)16-13(22)7-12(21)8-15(16)27-20/h3,5-8,21-24,26H,4H2,1-2H3
InChI KeyWOMWVGHYSNATOB-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Broussonetia papyriferaPlant
Glycyrrhiza glabraPlant
Glycyrrhiza uralensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3'-prenylated flavones
Alternative Parents
Substituents
  • 3'-prenylated flavone
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen 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
logP2.81ALOGPS
logP3.88ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)6.44ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity101.1 m³·mol⁻¹ChemAxon
Polarizability38.12 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039732
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019371
KNApSAcK IDC00005031
Chemspider ID4474523
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5315126
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available