Isoliquiritigenin

Identification

Name
Isoliquiritigenin
Accession Number
DB03285
Description

Isoliquiritigenin is a precursor to several flavonones in many plants.

Type
Small Molecule
Groups
Experimental
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Structure
Thumb
Weight
Average: 256.2534
Monoisotopic: 256.073558872
Chemical Formula
C15H12O4
Synonyms
  • (E)-1-(2,4-Dihydroxy-phenyl)-3-(4-hydroxy-phenyl)-propenone
  • (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propene-1-one
  • 2',4,4'-Trihydroxychalcone
  • 4,2',4'-Trihydroxychalcone
  • trans-2',4,4'-trihydroxychalcone
External IDs
  • GU 17
  • GU-17

Pharmacology

Indication
Not Available
Contraindications & Blackbox Warnings
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Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
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Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2'-hydroxychalcones. These are organic compounds containing chalcone skeleton that carries a hydroxyl group at the 2'-position.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Linear 1,3-diarylpropanoids
Sub Class
Chalcones and dihydrochalcones
Direct Parent
2'-Hydroxychalcones
Alternative Parents
Cinnamylphenols / Hydroxycinnamic acids and derivatives / Styrenes / Resorcinols / Benzoyl derivatives / Aryl ketones / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Enones
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Substituents
1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2'-hydroxychalcone / Acryloyl-group / Alpha,beta-unsaturated ketone / Aromatic homomonocyclic compound / Aryl ketone / Benzenoid / Benzoyl / Cinnamylphenol
show 12 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
chalcones (CHEBI:310312) / chalcones, Chalcones and dihydrochalcones (C08650) / Chalcones and dihydrochalcones (LMPK12120096)

Chemical Identifiers

UNII
B9CTI9GB8F
CAS number
961-29-5
InChI Key
DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChI
InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
IUPAC Name
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
SMILES
OC1=CC=C(\C=C\C(=O)C2=C(O)C=C(O)C=C2)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0037316
KEGG Compound
C08650
PubChem Compound
638278
PubChem Substance
46506198
ChemSpider
553829
BindingDB
50042944
ChEBI
310312
ChEMBL
CHEMBL129795
ZINC
ZINC000003869608
PDBe Ligand
HCC
Wikipedia
Isoliquiritigenin
PDB Entries
1fp1 / 4rlu / 5yx4 / 6ajv / 6ajx

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0551 mg/mLALOGPS
logP3.04ALOGPS
logP3.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity72.82 m3·mol-1ChemAxon
Polarizability26.66 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.6975
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.6032
P-glycoprotein inhibitor INon-inhibitor0.9216
P-glycoprotein inhibitor IINon-inhibitor0.9611
Renal organic cation transporterNon-inhibitor0.8802
CYP450 2C9 substrateNon-substrate0.732
CYP450 2D6 substrateNon-substrate0.9164
CYP450 3A4 substrateNon-substrate0.6823
CYP450 1A2 substrateInhibitor0.935
CYP450 2C9 inhibitorInhibitor0.8949
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorInhibitor0.7959
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8559
Ames testNon AMES toxic0.918
CarcinogenicityNon-carcinogens0.8639
BiodegradationNot ready biodegradable0.734
Rat acute toxicity2.0091 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9388
hERG inhibition (predictor II)Non-inhibitor0.9434
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTOF , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-014r-0900000000-e7c4095e90f57884e80c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0910000000-15db3efa5c81e3e8fc3e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-1930000000-6d143294fc9a6a343052

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

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