IMPPAT Phytochemical information: 
C15H18O7.C15H16O6
C15H18O7.C15H16O6
Summary

SMILES: CC(=C)[C@@H]1[C@@H]2OC(=O)[C@H]1[C@]1([C@]3([C@@H]2OC(=O)[C@]23[C@@H](C1)O2)C)O.O=C1O[C@H]2[C@H]([C@@H]1[C@]1(O)C[C@@H]3[C@]4([C@@]1([C@@H]2OC4=O)C)O3)C(O)(C)C
InChI: InChI=1S/C15H18O7.C15H16O6/c1-12(2,18)6-7-10(16)20-8(6)9-13(3)14(7,19)4-5-15(13,22-5)11(17)21-9;1-5(2)7-8-11(16)19-9(7)10-13(3)14(8,18)4-6-15(13,21-6)12(17)20-10/h5-9,18-19H,4H2,1-3H3;6-10,18H,1,4H2,2-3H3/t5-,6+,7+,8+,9-,13-,14-,15+;6-,7+,8+,9+,10-,13-,14-,15+/m11/s1
InChIKey: VJKUPQSHOVKBCO-NGKRNLQBSA-N
DeepSMILES: CC=C)[C@@H][C@@H]OC=O)[C@H]5[C@][C@][C@@H]7OC=O)[C@@]5[C@@H]C8)O3))))))C))O.O=CO[C@H][C@H][C@@H]5[C@]O)C[C@@H][C@][C@@]5[C@@H]9OC5=O))))C))O3))))))CO)C)C
Functional groups: C=C(C)C; COC(=O)C; C[C@H]1O[C@@]12CCOC2=O; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Furopyrans
NP Classifier Biosynthetic pathway: Terpenoids
NP Classifier Superclass: Sesquiterpenoids
NP Classifier Class: Picrotoxane sesquiterpenoids
Synonymous chemical names:
picrotoxin, picrotoxin (sesquiterpene glycoside)
External chemical identifiers:
CID:CID_5311359; SureChEMBL:SCHEMBL199981
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
C15H18O7.C15H16O6
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 602.59
Log P RDKit -0.93
Topological polar surface area (Å2) RDKit 190.95
Number of hydrogen bond acceptors RDKit 13
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 43
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 0
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 16
Stereochemical complexity RDKit 0.53
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 6
Number of sp3 hybridized carbon atoms RDKit 24
Shape complexity RDKit 0.8
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 6
Number of aliphatic rings RDKit 10
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 10
Number of saturated carbocycles RDKit 4
Number of saturated heterocycles RDKit 6
Number of saturated rings RDKit 10
Number of Smallest Set of Smallest Rings (SSSR) RDKit 10
C15H18O7.C15H16O6
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
Number of Ghose rule violations RDKit 4
Ghose rule RDKit Failed
Veber rule RDKit Bad
Egan rule RDKit Bad
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.15
C15H18O7.C15H16O6
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.17
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.19
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 3
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes