IMPPAT Phytochemical information: 
Neoipecoside
Neoipecoside
Summary

SMILES: C=C[C@H]1[C@@H](OC=C([C@H]1C[C@H]1N(CCc2c1c(O)c(cc2)O)C(=O)C)C(=O)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
InChI: InChI=1S/C27H35NO12/c1-4-14-15(9-17-20-13(5-6-18(31)21(20)32)7-8-28(17)12(2)30)16(25(36)37-3)11-38-26(14)40-27-24(35)23(34)22(33)19(10-29)39-27/h4-6,11,14-15,17,19,22-24,26-27,29,31-35H,1,7-10H2,2-3H3/t14-,15+,17-,19-,22-,23+,24-,26+,27+/m1/s1
InChIKey: XNYSLIQSJYSIDP-BCAAKZKISA-N
DeepSMILES: C=C[C@H][C@@H]OC=C[C@H]6C[C@H]NCCcc6cO)ccc6))O)))))))C=O)C))))))C=O)OC))))))O[C@@H]O[C@H]CO))[C@H][C@@H][C@H]6O))O))O
Scaffold Graph/Node/Bond level: C1=CC(CC2NCCc3ccccc32)CC(OC2CCCCO2)O1
Scaffold Graph/Node level: C1CCC(OC2CC(CC3NCCC4CCCCC43)CCO2)OC1
Scaffold Graph level: C1CCC(CC2CCCC(CC3CCCC4CCCCC43)C2)CC1
Functional groups: C=CC; COC(=O)C1=CO[C@@H](O[C@@H](C)OC)CC1; CC(=O)N(C)C; cO; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Prenol lipids
ClassyFire Subclass: Terpene glycosides
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Terpenoid tetrahydroisoquinoline alkaloids
Synonymous chemical names:
Neoipecoside, neoipecoside
External chemical identifiers:
CID:CID_21629955; ZINC:ZINC000145711038
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neoipecoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 565.57
Log P RDKit -0.42
Topological polar surface area (Å2) RDKit 195.68
Number of hydrogen bond acceptors RDKit 12
Number of hydrogen bond donors RDKit 6
Number of carbon atoms RDKit 27
Number of heavy atoms RDKit 40
Number of heteroatoms RDKit 13
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.33
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 15
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 4
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 4
Neoipecoside
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 4
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.14219
Neoipecoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
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 -10.00
Number of PAINS structural alerts SwissADME 2
Number of Brenk structural alerts SwissADME 2
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