Record Information
Version1.0
Creation date2010-04-08 22:07:53 UTC
Update date2019-11-26 03:01:56 UTC
Primary IDFDB008016
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameIrigenin
DescriptionIrigenin, also known as 5,7,3'-trihydroxy-6,4',5'-trimethoxyisoflavone, is a member of the class of compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. 3'-hydroxy,4'-methoxyisoflavonoids are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone. Thus, irigenin is considered to be a flavonoid lipid molecule. Irigenin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Irigenin can be synthesized from isoflavone. Irigenin can also be synthesized into iridin. Irigenin can be found in lima bean, which makes irigenin a potential biomarker for the consumption of this food product. Irigenin is an O-methylated isoflavone, a type of flavonoid. It can be isolated from the rhizomes of the leopard lily (Belamcanda chinensis), and Iris kemaonensis .
CAS Number548-76-5
Structure
Thumb
Synonyms
SynonymSource
5,7,3'-Trihydroxy-6,4',5'-trimethoxyisoflavoneChEBI
5,7,3'-Trimethoxy-6,4',5'-trimethoxyisoflavonebiospider
Irigeninbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.066 g/LALOGPS
logP2.74ALOGPS
logP2.6ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area114.68 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity91.07 m³·mol⁻¹ChemAxon
Polarizability35.6 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H16O8
IUPAC name5,7-dihydroxy-3-(3-hydroxy-4,5-dimethoxyphenyl)-6-methoxy-4H-chromen-4-one
InChI IdentifierInChI=1S/C18H16O8/c1-23-13-5-8(4-10(19)17(13)24-2)9-7-26-12-6-11(20)18(25-3)16(22)14(12)15(9)21/h4-7,19-20,22H,1-3H3
InChI KeyTUGWPJJTQNLKCL-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC(=CC(O)=C1OC)C1=COC2=CC(O)=C(OC)C(O)=C2C1=O
Average Molecular Weight360.3148
Monoisotopic Molecular Weight360.084517488
Classification
Description Belongs to the class of organic compounds known as 3'-hydroxy,4'-methoxyisoflavonoids. These are isoflavonoids carrying a methoxy group attached to the C4' atom, as well as a hydroxyl group at the C3'-position of the isoflavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent3'-hydroxy,4'-methoxyisoflavonoids
Alternative Parents
Substituents
  • 3p-methoxyisoflavone
  • 4p-o-methylisoflavone
  • 3'-hydroxy,4'-methoxyisoflavonoid
  • Isoflavone
  • Hydroxyisoflavonoid
  • Chromone
  • Methoxyphenol
  • Benzopyran
  • O-dimethoxybenzene
  • Dimethoxybenzene
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point185 oC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-0a49bcddb3944ca057a2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0009000000-ff78583aaebb27962885Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-1898000000-2affe7519ddc8a66fd4fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-abd823ba04e3a8d6df08Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0019000000-ca05046fe34ab08b198dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08mu-1193000000-7a5462f2fa78c135f32aSpectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC17957
Pubchem Compound ID5464170
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDIRIGENIN
BIGG IDNot Available
KNApSAcK IDC00009485
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cAMP-phosphodiesterase inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
cholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
hepatoprotective62868 Any compound that is able to prevent damage to the liver.DUKE
RNA-genicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).