IMPPAT Phytochemical information: 
Scopoletin
Scopoletin
Summary

SMILES: COc1cc2ccc(=O)oc2cc1O
InChI: InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
InChIKey: RODXRVNMMDRFIK-UHFFFAOYSA-N
DeepSMILES: COcccccc=O)oc6cc%10O
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: c=O; cOC; 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:
7-hydroxy-6-methoxy coumarin(scopoletin), 6-methoxy-7-hydroxycoumarin, Scopoletol, Scopoletin, scopoletol, scopoletin, β-methyl-aesculetin (scopoletin), scopoletin(6-methoxy-7-hydroxycoumarin), 6-methylxy-7-hydroxycoumarin, aesculin (β-methylaesculetin)
External chemical identifiers:
CID:CID_5280460; ChEMBL:CHEMBL71851; ChEBI:CHEBI:17488; ZINC:ZINC000000057733; FDASRS:KLF1HS0SXJ; SureChEMBL:SCHEMBL147702; MolPort-000-707-493
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Scopoletin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 192.17
Log P RDKit 1.51
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 10
Number of heavy atoms RDKit 14
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 1
Shape complexity RDKit 0.1
Number of rotatable bonds RDKit 1
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
Scopoletin
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 0.695448
Scopoletin
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 -6.39
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Scopoletin
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_000852ENSG00000069535MAOB4129ChEMBL, NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000804ENSG00000185015CA13377677ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000851ENSG00000189221MAOA4128ChEMBL, NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_001165ENSG00000241119UGT1A954600ChEMBL
TAR_EXP_000881ENSG00000087085ACHE43BindingDB, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053ChEMBL, NPASS
TAR_EXP_001092ENSG00000164307ERAP151752ChEMBL, NPASS
TAR_EXP_001125ENSG00000127445PIN15300NPASS
TAR_EXP_001160ENSG00000242515UGT1A1054575ChEMBL, NPASS
TAR_EXP_001161ENSG00000242366UGT1A854576ChEMBL, NPASS
TAR_EXP_000687ENSG00000100644HIF1A3091NPASS
TAR_EXP_001167ENSG00000244474UGT1A454657ChEMBL, NPASS
TAR_EXP_001168ENSG00000241635UGT1A154658ChEMBL, NPASS
TAR_EXP_001169ENSG00000288702UGT1A354659ChEMBL, NPASS
TAR_EXP_001206ENSG00000042088TDP155775NPASS
TAR_EXP_001299ENSG00000073756PTGS25743BindingDB, ChEMBL, NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000519ENSG00000171298GAA2548NPASS
TAR_EXP_000614ENSG00000087460GNAS2778NPASS
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_001660ENSG00000197888UGT2B177367ChEMBL
TAR_EXP_001659ENSG00000277132UGT2B157366ChEMBL, NPASS
TAR_EXP_001553ENSG00000140263SORD6652BindingDB, NPASS
TAR_EXP_001488ENSG00000164308ERAP264167ChEMBL, NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001362ENSG00000173039RELA5970ChEMBL, NPASS
TAR_EXP_001360ENSG00000004700RECQL5965NPASS
TAR_EXP_000263ENSG00000140505CYP1A21544NPASS
TAR_EXP_000096ENSG00000173610UGT2A110941ChEMBL
TAR_EXP_000095ENSG00000224143EHMT210919NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_000456ENSG00000085662AKR1B1231ChEMBL, NPASS
TAR_EXP_000500ENSG00000275565ALOX5240BindingDB, ChEMBL, NPASS
TAR_EXP_000567ENSG00000177628GBA12629NPASS
TAR_EXP_000572ENSG00000108773KAT2A2648ChEMBL, NPASS
TAR_EXP_000576ENSG00000127554GFER2671ChEMBL, NPASS
TAR_EXP_000593ENSG00000102393GLA2717NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000556ENSG00000111640GAPDH2597BindingDB, NPASS