IMPPAT Phytochemical information: 
Menispermacide
Menispermacide
Summary

SMILES: O=C1O[C@H](C[C@]2([C@@H]1C[C@H]1OC(=O)[C@@]34[C@@]1([C@H]2CC[C@H]4O3)C)C)c1cocc1
InChI: InChI=1S/C20H22O6/c1-18-8-12(10-5-6-23-9-10)24-16(21)11(18)7-15-19(2)13(18)3-4-14-20(19,26-14)17(22)25-15/h5-6,9,11-15H,3-4,7-8H2,1-2H3/t11-,12-,13+,14-,15-,18+,19-,20+/m1/s1
InChIKey: KVBXJYXBQNJSPF-SJOQVHCZSA-N
DeepSMILES: O=CO[C@H]C[C@][C@@H]6C[C@H]OC=O)[C@][C@@]5[C@H]9CC[C@H]6O7)))))C))))))))C)))ccocc5
Scaffold Graph/Node/Bond level: O=C1OC(c2ccoc2)CC2C1CC1OC(=O)C34OC3CCC2C14
Scaffold Graph/Node level: OC1OC(C2CCOC2)CC2C1CC1OC(O)C34OC3CCC2C14
Scaffold Graph level: CC1CC(C2CCCC2)CC2C1CC1CC(C)C34CC3CCC2C14
Functional groups: COC(=O)C; C[C@H]1O[C@@]12CCOC2=O; coc
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Naphthopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Diterpenoids
NP Classifier Class: Colensane and Clerodane diterpenoids
Synonymous chemical names:
Menispermacide, menispermacide
External chemical identifiers:
CID:CID_101632302
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Menispermacide
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 358.39
Log P RDKit 2.77
Topological polar surface area (Å2) RDKit 78.27
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.4
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.7
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 2
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 2
Number of saturated heterocycles RDKit 3
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Menispermacide
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.567369
Menispermacide
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.85
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 No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No