IMPPAT Phytochemical information: 
Daphnoretin
Daphnoretin
Summary

SMILES: COc1cc2cc(Oc3ccc4c(c3)oc(=O)cc4)c(=O)oc2cc1O
InChI: InChI=1S/C19H12O7/c1-23-16-6-11-7-17(19(22)26-15(11)9-13(16)20)24-12-4-2-10-3-5-18(21)25-14(10)8-12/h2-9,20H,1H3
InChIKey: JRHMMVBOTXEHGJ-UHFFFAOYSA-N
DeepSMILES: COcccccOcccccc6)oc=O)cc6))))))))))c=O)oc6cc%10O
Scaffold Graph/Node/Bond level: O=c1ccc2ccc(Oc3cc4ccccc4oc3=O)cc2o1
Scaffold Graph/Node level: OC1CCC2CCC(OC3CC4CCCCC4OC3O)CC2O1
Scaffold Graph level: CC1CCC2CCC(CC3CC4CCCCC4CC3C)CC2C1
Functional groups: cOC; cOc; coc; c=O; 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:
Daphnoretin, daphnoretin, c19h12o7
External chemical identifiers:
CID:CID_5281406; ChEMBL:CHEMBL508494; ChEBI:CHEBI:4324; ZINC:ZINC000000689683; FDASRS:1A7Q3KY3LH; SureChEMBL:SCHEMBL13784417; MolPort-002-532-429
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Daphnoretin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.3
Log P RDKit 3.41
Topological polar surface area (Å2) RDKit 99.11
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 7
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 18
Number of sp3 hybridized carbon atoms RDKit 1
Shape complexity RDKit 0.05
Number of rotatable bonds RDKit 3
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
Daphnoretin
Drug-likeness properties
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 0.564088
Daphnoretin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.14
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 Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No