Isoliquiritigenin

Identification

Generic Name
Isoliquiritigenin
DrugBank Accession Number
DB03285
Background

Isoliquiritigenin is a precursor to several flavonones in many plants.

Type
Small Molecule
Groups
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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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/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
show 3 more
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)
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

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-MSsplash10-000i-1970000000-6164f65f5d6241a006f8
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-0a4i-0000009000-afd1640b539ec58a4616
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0000009000-afd1640b539ec58a4616
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSsplash10-014r-0900000000-e7c4095e90f57884e80c
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSsplash10-0a4i-0090000000-788e4464b6a542aa7c22
LC-MS/MS Spectrum - LC-ESI-qTOF , PositiveLC-MS/MSsplash10-000i-0910000000-15db3efa5c81e3e8fc3e
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0980000000-01fe4c779c74d26a2eab
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0190000000-1164503978088e3ed3dd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-0940000000-aeb0f204bbb02fa3e5ed
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052r-0960000000-390abe9a2058702d0020
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-9800000000-d31976b8b06652e5a429
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0910000000-12cda2735e43ad8e10e8
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-177.6250444
predicted
DarkChem Lite v0.1.0
[M-H]-167.988451
predicted
DarkChem Standard v0.1.0
[M-H]-177.2562444
predicted
DarkChem Lite v0.1.0
[M-H]-177.8343444
predicted
DarkChem Lite v0.1.0
[M-H]-164.51949
predicted
DeepCCS 1.0 (2019)
[M+H]+182.4076444
predicted
DarkChem Lite v0.1.0
[M+H]+178.4766236
predicted
DarkChem Standard v0.1.0
[M+H]+179.4342444
predicted
DarkChem Lite v0.1.0
[M+H]+179.8747444
predicted
DarkChem Lite v0.1.0
[M+H]+166.87749
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.4320444
predicted
DarkChem Lite v0.1.0
[M+Na]+177.3314635
predicted
DarkChem Standard v0.1.0
[M+Na]+178.5082444
predicted
DarkChem Lite v0.1.0
[M+Na]+177.9449444
predicted
DarkChem Lite v0.1.0
[M+Na]+172.97063
predicted
DeepCCS 1.0 (2019)

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