IMPPAT Phytochemical information: 
Coumestrol

Coumestrol
Summary

SMILES: Oc1ccc2c(c1)oc(=O)c1c2oc2c1ccc(c2)O
InChI: InChI=1S/C15H8O5/c16-7-1-3-9-11(5-7)19-14-10-4-2-8(17)6-12(10)20-15(18)13(9)14/h1-6,16-17H
InChIKey: ZZIALNLLNHEQPJ-UHFFFAOYSA-N
DeepSMILES: Occcccc6)oc=O)cc6occ5cccc6)O
Scaffold Graph/Node/Bond level: O=c1oc2ccccc2c2oc3ccccc3c12
Scaffold Graph/Node level: OC1OC2CCCCC2C2OC3CCCCC3C12
Scaffold Graph level: CC1CC2CCCCC2C2CC3CCCCC3C12
Functional groups: cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Isoflavonoids
ClassyFire Subclass: Coumestans
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Isoflavonoids
NP Classifier Class: Coumestan
Synonymous chemical names:
cumestrol, Cumestrol, coumesterol, coumestrol, Coumestrol
External chemical identifiers:
CID:CID_5281707; ChEMBL:CHEMBL30707; ChEBI:CHEBI:3908; ZINC:ZINC000000001219; FDASRS:V7NW98OB34; SureChEMBL:SCHEMBL22012; MolPort-003-846-031
Chemical structure download


Coumestrol
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 268.22
Log P RDKit 3.1
Topological polar surface area (Å2) RDKit 83.81
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 5
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 0
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 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 4
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 4


Coumestrol
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 0.478597


Coumestrol
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.98
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No


Coumestrol
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_000853ENSG00000276155MAPT4137ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000968ENSG00000109320NFKB14790NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000966ENSG00000116044NFE2L24780ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001059ENSG00000122008POLK51426NPASS
TAR_EXP_001066ENSG00000132196HSD17B751478ChEMBL, NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001139ENSG00000166851PLK15347NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000773ENSG00000169083AR367NPASS
TAR_EXP_000720ENSG00000106211HSPB13315NPASS
TAR_EXP_001150ENSG00000070501POLB5423ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_000650ENSG00000161800RACGAP129127ChEMBL, NPASS
TAR_EXP_000619ENSG00000254598CSNK2A3283106ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234NPASS
TAR_EXP_000608ENSG00000115419GLS2744ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000350ENSG00000106546AHR196NPASS
TAR_EXP_001151ENSG00000170734POLH5429NPASS
TAR_EXP_001676ENSG00000165392WRN7486NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000397ENSG00000140009ESR22100ChEMBL, NPASS
TAR_EXP_001170ENSG00000112033PPARD5467NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000132ENSG00000137491SLCO2B111309NPASS
TAR_EXP_000231ENSG00000101266CSNK2A11457BindingDB, ChEMBL, NPASS
TAR_EXP_000232ENSG00000070770CSNK2A21459ChEMBL, NPASS
TAR_EXP_000234ENSG00000230700CSNK2B1460ChEMBL, NPASS
TAR_EXP_001851ENSG00000282607MGAM8972ChEMBL
TAR_EXP_001836ENSG00000144852NR1I28856ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_001665ENSG00000111424VDR7421NPASS
TAR_EXP_001360ENSG00000004700RECQL5965ChEMBL, NPASS
TAR_EXP_001728ENSG00000176208ATAD579915NPASS
TAR_EXP_001461ENSG00000186350RXRA6256NPASS
TAR_EXP_001485ENSG00000197299BLM641NPASS
TAR_EXP_000395ENSG00000091831ESR12099ChEMBL, NPASS
TAR_EXP_001609ENSG00000151090THRB7068NPASS
TAR_EXP_001663ENSG00000162607USP17398NPASS
TAR_EXP_001549ENSG00000166311SMPD16609NPASS
TAR_EXP_001652ENSG00000116030SUMO17341ChEMBL, NPASS