IMPPAT Phytochemical information: 
Formononetin
Formononetin
Summary

SMILES: COc1ccc(cc1)c1coc2c(c1=O)ccc(c2)O
InChI: InChI=1S/C16H12O4/c1-19-12-5-2-10(3-6-12)14-9-20-15-8-11(17)4-7-13(15)16(14)18/h2-9,17H,1H3
InChIKey: HKQYGTCOTHHOMP-UHFFFAOYSA-N
DeepSMILES: COcccccc6))ccoccc6=O))cccc6)O
Scaffold Graph/Node/Bond level: O=c1c(-c2ccccc2)coc2ccccc12
Scaffold Graph/Node level: OC1C(C2CCCCC2)COC2CCCCC21
Scaffold Graph level: CC1C2CCCCC2CCC1C1CCCCC1
Functional groups: cOC; coc; cO; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: O-methylated isoflavonoids
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Isoflavones
Synonymous chemical names:
formononetin, biochanin b, 7-hydroxy-4'-methoxyisoflavone, Formononetin
External chemical identifiers:
CID:CID_5280378; ChEMBL:CHEMBL242341; ChEBI:CHEBI:18088; ZINC:ZINC000018847036; FDASRS:295DQC67BJ; SureChEMBL:SCHEMBL62915; MolPort-000-450-946
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Formononetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 268.27
Log P RDKit 3.17
Topological polar surface area (Å2) RDKit 59.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
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 1
Shape complexity RDKit 0.06
Number of rotatable bonds RDKit 2
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 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 3
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 3
Formononetin
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.775103
Formononetin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.95
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No
Formononetin
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_000773ENSG00000169083AR367NPASS
TAR_EXP_000756ENSG00000109471IL23558ChEMBL, NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000276ENSG00000272532CYP2D61565NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_000264ENSG00000138061CYP1B11545BindingDB, ChEMBL, NPASS
TAR_EXP_000262ENSG00000140465CYP1A11543BindingDB, ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000004ENSG00000094631HDAC610013ChEMBL
TAR_EXP_001547ENSG00000275349SMN16606ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_001621ENSG00000141510TP537157NPASS
TAR_EXP_001557ENSG00000012048BRCA1672NPASS
TAR_EXP_001647ENSG00000077498TYR7299ChEMBL, NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_001306ENSG00000196396PTPN15770ChEMBL, NPASS
TAR_EXP_001300ENSG00000160801PTH1R5745NPASS
TAR_EXP_001273ENSG00000100804PSMB55693BindingDB, ChEMBL, NPASS
TAR_EXP_001171ENSG00000132170PPARG5468ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467ChEMBL, NPASS
TAR_EXP_001105ENSG00000082175PGR5241ChEMBL, NPASS
TAR_EXP_000969ENSG00000077150NFKB24791ChEMBL
TAR_EXP_000968ENSG00000109320NFKB14790ChEMBL, NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_000898ENSG00000103222ABCC14363ChEMBL
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_001166ENSG00000186951PPARA5465ChEMBL, NPASS
TAR_EXP_001512ENSG00000100170SLC5A16523ChEMBL, NPASS
TAR_EXP_001513ENSG00000140675SLC5A26524ChEMBL, NPASS