IMPPAT Phytochemical information: 
Fraxetin
Fraxetin
Summary

SMILES: COc1cc2ccc(=O)oc2c(c1O)O
InChI: InChI=1S/C10H8O5/c1-14-6-4-5-2-3-7(11)15-10(5)9(13)8(6)12/h2-4,12-13H,1H3
InChIKey: HAVWRBANWNTOJX-UHFFFAOYSA-N
DeepSMILES: COcccccc=O)oc6cc%10O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccccc2o1
Scaffold Graph/Node level: OC1CCC2CCCCC2O1
Scaffold Graph level: CC1CCC2CCCCC2C1
Functional groups: cOC; c=O; coc; cO
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:
Fraxetin, fraxetin
External chemical identifiers:
CID:CID_5273569; ChEMBL:CHEMBL54909; ChEBI:CHEBI:5169; ZINC:ZINC000000113309; FDASRS:CD3GD44O3K; SureChEMBL:SCHEMBL43472; MolPort-001-683-945
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fraxetin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 208.17
Log P RDKit 1.21
Topological polar surface area (Å2) RDKit 79.9
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 10
Number of heavy atoms RDKit 15
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 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
Fraxetin
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 0.54354
Fraxetin
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 -6.74
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No
Fraxetin
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_000608ENSG00000115419GLS2744NPASS
TAR_EXP_000411ENSG00000165092ALDH1A1216NPASS
TAR_EXP_001206ENSG00000042088TDP155775ChEMBL, NPASS
TAR_EXP_000433ENSG00000168496FEN12237ChEMBL, NPASS
TAR_EXP_000017ENSG00000169371SNUPN10073NPASS
TAR_EXP_000503ENSG00000161905ALOX15246ChEMBL, NPASS
TAR_EXP_000604ENSG00000112164GLP1R2740NPASS
TAR_EXP_000864ENSG00000143384MCL14170BindingDB, ChEMBL, NPASS
TAR_EXP_000616ENSG00000111700SLCO1B328234ChEMBL, NPASS
TAR_EXP_001059ENSG00000122008POLK51426ChEMBL, NPASS
TAR_EXP_001689ENSG00000168748CA7766BindingDB, ChEMBL, NPASS
TAR_EXP_001031ENSG00000112312GMNN51053NPASS
TAR_EXP_000880ENSG00000118058KMT2A4297NPASS
TAR_EXP_001690ENSG00000107159CA9768BindingDB, ChEMBL, NPASS
TAR_EXP_001691ENSG00000074410CA12771BindingDB, ChEMBL, NPASS
TAR_EXP_001753ENSG00000137752CASP1834NPASS
TAR_EXP_001764ENSG00000165806CASP7840NPASS
TAR_EXP_001923ENSG00000066135KDM4A9682ChEMBL, NPASS
TAR_EXP_000119ENSG00000101751POLI11201NPASS
TAR_EXP_000814ENSG00000108424KPNB13837NPASS
TAR_EXP_000819ENSG00000235268KDM4E390245NPASS
TAR_EXP_000853ENSG00000276155MAPT4137NPASS
TAR_EXP_001684ENSG00000104267CA2760BindingDB, ChEMBL, NPASS
TAR_EXP_001344ENSG00000132341RAN5901NPASS
TAR_EXP_001298ENSG00000095303PTGS15742NPASS
TAR_EXP_001468ENSG00000204842ATXN26311NPASS
TAR_EXP_001230ENSG00000100030MAPK15594NPASS
TAR_EXP_000676ENSG00000072506HSD17B103028ChEMBL, NPASS
TAR_EXP_000061ENSG00000134538SLCO1B110599ChEMBL, NPASS
TAR_EXP_000701ENSG00000164120HPGD3248NPASS
TAR_EXP_001547ENSG00000275349SMN16606NPASS
TAR_EXP_000273ENSG00000138109CYP2C91559NPASS
TAR_EXP_000706ENSG00000291796APEX1328NPASS
TAR_EXP_000271ENSG00000165841CYP2C191557NPASS
TAR_EXP_001683ENSG00000133742CA1759BindingDB, ChEMBL, NPASS
TAR_EXP_000804ENSG00000185015CA13377677ChEMBL, NPASS