IMPPAT Phytochemical information: 
Daphnin
Daphnin
Summary

SMILES: OC[C@H]1O[C@@H](Oc2ccc3c(c2O)oc(=O)cc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C15H16O9/c16-5-8-10(18)12(20)13(21)15(23-8)22-7-3-1-6-2-4-9(17)24-14(6)11(7)19/h1-4,8,10,12-13,15-16,18-21H,5H2/t8-,10-,12+,13-,15-/m1/s1
InChIKey: HOIXTKAYCMNVMY-PVOAASPHSA-N
DeepSMILES: OC[C@H]O[C@@H]Occcccc6O))oc=O)cc6))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: O=c1ccc2ccc(OC3CCCCO3)cc2o1
Scaffold Graph/Node level: OC1CCC2CCC(OC3CCCCO3)CC2O1
Scaffold Graph level: CC1CCC2CCC(CC3CCCCC3)CC2C1
Functional groups: CO; cO[C@@H](C)OC; cO; coc; c=O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
ClassyFire Subclass: Coumarin glycosides
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
daphnoside, Daphnin, daphnin
External chemical identifiers:
CID:CID_439499; ChEMBL:CHEMBL1879316; ChEBI:CHEBI:17989; ZINC:ZINC000004095653; FDASRS:K4REW3G17G; SureChEMBL:SCHEMBL127932
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Daphnin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 340.28
Log P RDKit -1.32
Topological polar surface area (Å2) RDKit 149.82
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 5
Number of carbon atoms RDKit 15
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.4
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Daphnin
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 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.428515
Daphnin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -8.81
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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