Identification

Generic Name
Isoliquiritigenin
DrugBank Accession Number
DB03285
Background

Isoliquiritigenin is a precursor to several flavonones in many plants.

Type
Small Molecule
Experimental
Structure
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

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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

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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 byClassyfire
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奔驰enoids/1-hydroxy-2-unsubstituted benzenoids/Vinylogous acids/Enones
show 3 more
Substituents
1-hydroxy-2-unsubstituted benzenoid/1-hydroxy-4-unsubstituted奔驰enoid/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)
Affected organisms
Not Available

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

一般引用
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 TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

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
Property Value Source
Water Solubility 0.0551 mg/mL ALOGPS
logP 3.04 ALOGPS
logP 3.63 Chemaxon
logS -3.7 ALOGPS
pKa (Strongest Acidic) 7.11 Chemaxon
pKa (Strongest Basic) -6.4 Chemaxon
Physiological Charge -1 Chemaxon
Hydrogen Acceptor Count 4 Chemaxon
Hydrogen Donor Count 3 Chemaxon
Polar Surface Area 77.76 Å2 Chemaxon
Rotatable Bond Count 3 Chemaxon
Refractivity 72.82 m3·mol-1 Chemaxon
Polarizability 26.66 Å3 Chemaxon
Number of Rings 2 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule No Chemaxon
MDDR-like规则 No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 0.9894
Blood Brain Barrier + 0.6975
Caco-2 permeable + 0.8867
P-glycoprotein substrate Non-substrate 0.6032
P-glycoprotein inhibitor I Non-inhibitor 0.9216
P-glycoprotein inhibitor II Non-inhibitor 0.9611
Renal organic cation transporter Non-inhibitor 0.8802
CYP450 2C9 substrate Non-substrate 0.732
CYP450 2D6 substrate Non-substrate 0.9164
CYP450 3A4 substrate Non-substrate 0.6823
CYP450 1A2 substrate Inhibitor 0.935
CYP450 2C9 inhibitor Inhibitor 0.8949
CYP450 2D6 inhibitor Non-inhibitor 0.9231
CYP450 2C19 inhibitor Inhibitor 0.8994
CYP450 3A4 inhibitor Inhibitor 0.7959
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8559
Ames test Non AMES toxic 0.918
Carcinogenicity Non-carcinogens 0.8639
Biodegradation Not ready biodegradable 0.734
Rat acute toxicity 2.0091 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9388
hERG inhibition (predictor II) Non-inhibitor 0.9434
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
MS/MS Spectrum - ESI-TOF 20V, Negative LC-MS/MS Not Available
MS/MS Spectrum - ESI-TOF 10V, Negative LC-MS/MS Not Available
MS/MS Spectrum - ESI-TOF 20V, Negative LC-MS/MS Not Available
MS/MS Spectrum - ESI-TOF 10V, Negative LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-qTOF , Positive LC-MS/MS Not Available
LC-MS/MS Spectrum - LC-ESI-TOF , negative LC-MS/MS splash10-014r-0900000000-e7c4095e90f57884e80c
MS/MS Spectrum - , positive LC-MS/MS splash10-000i-0910000000-15db3efa5c81e3e8fc3e
MS/MS Spectrum - , positive LC-MS/MS splash10-000i-1930000000-6d143294fc9a6a343052

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52