IMPPAT Phytochemical information: 
Esculetin
Esculetin
Summary

SMILES: O=c1ccc2c(o1)cc(c(c2)O)O
InChI: InChI=1S/C9H6O4/c10-6-3-5-1-2-9(12)13-8(5)4-7(6)11/h1-4,10-11H
InChIKey: ILEDWLMCKZNDJK-UHFFFAOYSA-N
DeepSMILES: O=ccccco6)cccc6)O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: c=O; cO; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Hydroxycoumarins
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
6,7-dihydroxy-coumarin, 6,7-dihydroxycoumarin (aesculetin), 67-dihydroxycoumarin, Esculetin, 6,7-dihydroxycoumarin, esculetin, aesculetin
External chemical identifiers:
CID:CID_5281416; ChEMBL:CHEMBL244743; ChEBI:CHEBI:490095; ZINC:ZINC000000057908; FDASRS:SM2XD6V944; SureChEMBL:SCHEMBL24641; MolPort-000-709-311
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Esculetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 178.14
Log P RDKit 1.2
Topological polar surface area (Å2) RDKit 70.67
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 9
Number of heavy atoms RDKit 13
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 9
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 1
Number of aromatic heterocycles RDKit 1
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
Esculetin
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 1
Ghose filter RDKit Failed
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 0.469412
Esculetin
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.52
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Esculetin
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_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_000519ENSG00000171298GAA2548ChEMBL, NPASS
TAR_EXP_000833ENSG00000160789LMNA4000NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_000860ENSG00000152601MBNL14154NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_000876ENSG00000276701MIF4282BindingDB, ChEMBL
TAR_EXP_000895ENSG00000178802MPI4351BindingDB, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001092ENSG00000164307ERAP151752ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001678ENSG00000158125XDH7498BindingDB, ChEMBL, NPASS
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001553ENSG00000140263SORD6652BindingDB, ChEMBL, NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_001488ENSG00000164308ERAP264167ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_001298ENSG00000095303PTGS15742ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000747ENSG00000138413IDH13417NPASS
TAR_EXP_000491ENSG00000186318BACE123621BindingDB, ChEMBL, NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000280ENSG00000160868CYP3A41576NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544NPASS
TAR_EXP_000503ENSG00000161905ALOX15246NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682NPASS
TAR_EXP_000766ENSG00000131203IDO13620NPASS
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000076ENSG00000117139KDM5B10765ChEMBL
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_000715ENSG00000044574HSPA53309NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091ChEMBL, NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS