IMPPAT Phytochemical information: 
Isoliquiritigenin
Isoliquiritigenin
Summary

SMILES: Oc1ccc(cc1)/C=C/C(=O)c1ccc(cc1O)O
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+
InChIKey: DXDRHHKMWQZJHT-FPYGCLRLSA-N
DeepSMILES: Occcccc6))/C=C/C=O)cccccc6O)))O
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)c1ccccc1
Scaffold Graph/Node level: OC(CCC1CCCCC1)C1CCCCC1
Scaffold Graph level: CC(CCC1CCCCC1)C1CCCCC1
Functional groups: cO; c/C=C/C(c)=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Linear 1,3-diarylpropanoids
ClassyFire Subclass: Chalcones and dihydrochalcones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Flavonoids
NP Classifier Class: Chalcones
Synonymous chemical names:
isoliquiritigenin, isoliquirtigenin, 424-trihydroxychalcone, liquiritigenin iso, 4,2',4'-trihydroxy-chalcone, isoliquiritigenin (2-,4 ',4-trihydroxychalcone), Isoliquiritigenin
External chemical identifiers:
CID:CID_638278; ChEMBL:CHEMBL129795; ChEBI:CHEBI:310312; ZINC:ZINC000003869608; FDASRS:B9CTI9GB8F; SureChEMBL:SCHEMBL161168; MolPort-001-741-660
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isoliquiritigenin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 256.26
Log P RDKit 2.7
Topological polar surface area (Å2) RDKit 77.76
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 19
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 0
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 2
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 2
Isoliquiritigenin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.582503
Isoliquiritigenin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.61
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Isoliquiritigenin
Phytochemical - Human target proteins supported by experimental evidence associations
Human target proteins supported by experimental evidence
IMPPAT target identifierGene identifierHGNC symbolEntrez Gene identifierSource
TAR_EXP_001544ENSG00000080503SMARCA26595BindingDB, NPASS
TAR_EXP_001207ENSG00000154229PRKCA5578ChEMBL
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001173ENSG00000196199MPHOSPH854737NPASS
TAR_EXP_001171ENSG00000132170PPARG5468ChEMBL, NPASS
TAR_EXP_001141ENSG00000109099PMP225376NPASS
TAR_EXP_001209ENSG00000166501PRKCB5579ChEMBL
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_001013ENSG00000185624P4HB5034BindingDB, ChEMBL
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000891ENSG00000137745MMP134322BindingDB, ChEMBL
TAR_EXP_000888ENSG00000100985MMP94318BindingDB, ChEMBL, NPASS
TAR_EXP_000886ENSG00000137673MMP74316BindingDB, ChEMBL
TAR_EXP_000885ENSG00000149968MMP34314ChEMBL
TAR_EXP_000884ENSG00000087245MMP24313ChEMBL
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001212ENSG00000163932PRKCD5580ChEMBL
TAR_EXP_001215ENSG00000027075PRKCH5583ChEMBL
TAR_EXP_001214ENSG00000126583PRKCG5582ChEMBL
TAR_EXP_001665ENSG00000111424VDR7421ChEMBL, NPASS
TAR_EXP_001663ENSG00000162607USP17398ChEMBL, NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001554ENSG00000291971SRC6714ChEMBL, NPASS
TAR_EXP_001551ENSG00000145335SNCA6622NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001213ENSG00000171132PRKCE5581ChEMBL
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB
TAR_EXP_001298ENSG00000095303PTGS15742NPASS
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS
TAR_EXP_001227ENSG00000067606PRKCZ5590ChEMBL
TAR_EXP_001226ENSG00000065675PRKCQ5588ChEMBL
TAR_EXP_001223ENSG00000184304PRKD15587ChEMBL
TAR_EXP_001216ENSG00000163558PRKCI5584ChEMBL
TAR_EXP_000883ENSG00000196611MMP14312ChEMBL
TAR_EXP_001306ENSG00000196396PTPN15770BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000845ENSG00000166949SMAD34088NPASS
TAR_EXP_000433ENSG00000168496FEN12237NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL, NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_000348ENSG00000146648EGFR1956ChEMBL, NPASS
TAR_EXP_000324ENSG00000184845DRD11812NPASS
TAR_EXP_000285ENSG00000137869CYP19A11588BindingDB, ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576ChEMBL, NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557ChEMBL, NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543ChEMBL, NPASS
TAR_EXP_000155ENSG00000162711NLRP3114548BindingDB, ChEMBL, NPASS
TAR_EXP_000146ENSG00000175344CHRNA71139BindingDB, ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000097ENSG00000108468CBX110951NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS
TAR_EXP_000438ENSG00000077782FGFR12260ChEMBL, NPASS
TAR_EXP_000440ENSG00000066468FGFR22263ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915ChEMBL, NPASS
TAR_EXP_000818ENSG00000187258NPSR1387129NPASS
TAR_EXP_000811ENSG00000157404KIT3815ChEMBL, NPASS
TAR_EXP_000810ENSG00000128052KDR3791ChEMBL, NPASS
TAR_EXP_000798ENSG00000055118KCNH23757ChEMBL, NPASS
TAR_EXP_000786ENSG00000177606JUN3725ChEMBL
TAR_EXP_000752ENSG00000142192APP351BindingDB, ChEMBL, NPASS
TAR_EXP_000747ENSG00000138413IDH13417ChEMBL, NPASS
TAR_EXP_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000709ENSG00000108786HSD17B13292BindingDB, ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000567ENSG00000177628GBA12629ChEMBL, NPASS
TAR_EXP_000505ENSG00000198793MTOR2475NPASS
TAR_EXP_000496ENSG00000115825PRKD323683ChEMBL
TAR_EXP_000711ENSG00000086696HSD17B23294BindingDB, ChEMBL, NPASS
TAR_EXP_000008ENSG00000153094BCL2L1110018BindingDB
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL