IMPPAT Phytochemical information: 
Toddalosin
Toddalosin
Summary

SMILES: COc1cc(OC)c(c2c1ccc(=O)o2)[C@@H]([C@@H]1[C@H](C=C(CC1(C)C)C)c1c(OC)cc(c2c1oc(=O)cc2)OC)O
InChI: InChI=1S/C32H34O9/c1-16-12-19(26-22(38-6)13-20(36-4)17-8-10-24(33)40-30(17)26)28(32(2,3)15-16)29(35)27-23(39-7)14-21(37-5)18-9-11-25(34)41-31(18)27/h8-14,19,28-29,35H,15H2,1-7H3/t19-,28+,29+/m1/s1
InChIKey: VCSIERORKAMAIV-FWEOMDSASA-N
DeepSMILES: COcccOC))ccc6ccc=O)o6))))))[C@@H][C@@H][C@H]C=CCC6C)C)))C)))ccOC))cccc6oc=O)cc6))))))OC))))))))O
Scaffold Graph/Node/Bond level: O=c1ccc2cccc(CC3CCC=CC3c3cccc4ccc(=O)oc34)c2o1
Scaffold Graph/Node level: OC1CCC2CCCC(CC3CCCCC3C3CCCC4CCC(O)OC43)C2O1
Scaffold Graph level: CC1CCC2CCCC(CC3CCCCC3C3CCCC4CCC(C)CC43)C2C1
Functional groups: cOC; coc; c=O; CO; CC(C)=CC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Phenylpropanoids and polyketides
ClassyFire Class: Coumarins and derivatives
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Coumarins
NP Classifier Class: Simple coumarins
Synonymous chemical names:
toddalosin
External chemical identifiers:
CID:CID_15071281; ZINC:ZINC000096023598
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Toddalosin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 562.62
Log P RDKit 5.74
Topological polar surface area (Å2) RDKit 117.57
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 32
Number of heavy atoms RDKit 41
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.09
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 20
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.38
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 0
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 5
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 5
Toddalosin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.222087
Toddalosin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Poorly soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -6.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 2
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes