IMPPAT Phytochemical information: 
4-Desoxypicropodophyllotoxin

4-Desoxypicropodophyllotoxin
Summary

SMILES: COc1cc(OC)c(cc1[C@H]1[C@@H]2C(=O)OC[C@@H]2Cc2c1cc1OCOc1c2)OC
InChI: InChI=1S/C22H22O7/c1-24-15-8-17(26-3)16(25-2)7-14(15)21-13-6-19-18(28-10-29-19)5-11(13)4-12-9-27-22(23)20(12)21/h5-8,12,20-21H,4,9-10H2,1-3H3/t12-,20+,21-/m0/s1
InChIKey: TUGXVGMIXLPLHW-QDEDPJFRSA-N
DeepSMILES: COcccOC))ccc6[C@H][C@@H]C=O)OC[C@@H]5Ccc9ccOCOc5c9))))))))))))))))))OC
Scaffold Graph/Node/Bond level: O=C1OCC2Cc3cc4c(cc3C(c3ccccc3)C12)OCO4
Scaffold Graph/Node level: OC1OCC2CC3CC4OCOC4CC3C(C3CCCCC3)C21
Scaffold Graph level: CC1CCC2CC3CC4CCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; COC(=O)C; c1cOCO1
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lignans, neolignans and related compounds
ClassyFire Class: Lignan lactones
NP Classifier Biosynthetic pathway: Shikimates and Phenylpropanoids
NP Classifier Superclass: Lignans
NP Classifier Class: Arylnaphthalene and aryltetralin lignans
Synonymous chemical names:
desoxypicropodophyllin
External chemical identifiers:
CID:CID_56841131
Chemical structure download


4-Desoxypicropodophyllotoxin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 398.41
Log P RDKit 2.92
Topological polar surface area (Å2) RDKit 72.45
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.14
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.41
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5


4-Desoxypicropodophyllotoxin
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.73


4-Desoxypicropodophyllotoxin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately 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 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No