IMPPAT Phytochemical information: 
Seneciphylline
Seneciphylline
Summary

SMILES: C/C=C\1/CC(=C)[C@@](C)(O)C(=O)OCC2=CCN3[C@H]2[C@H](OC1=O)CC3
InChI: InChI=1S/C18H23NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,14-15,22H,2,6-10H2,1,3H3/b12-4-/t14-,15-,18-/m1/s1
InChIKey: FCEVNJIUIMLVML-QPSVUOIXSA-N
DeepSMILES: C/C=C/CC=C)[C@@]C)O)C=O)OCC=CCN[C@H]5[C@H]OC/%15=O)))CC5
Scaffold Graph/Node/Bond level: C=C1CC(=C)C(=O)OC2CCN3CC=C(COC(=O)C1)C23
Scaffold Graph/Node level: CC1CC(O)OCC2CCN3CCC(OC(O)C(C)C1)C23
Scaffold Graph level: CC1CCC2CCC3CCC(CC(C)C(C)CC(C)C1)C23
Functional groups: C/C=C(/C)C(=O)OC; C=C(C)C; CO; COC(=O)C; CC=C(C)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Ornithine alkaloids
NP Classifier Class: Pyrrolizidine alkaloids
Synonymous chemical names:
seneciophylline, Seneciphylline, jacodine, seneciphylline
External chemical identifiers:
CID:CID_5281750; ChEMBL:CHEMBL523911; ChEBI:CHEBI:9108; ZINC:ZINC000095627757; FDASRS:0ZYZ9L5454; SureChEMBL:SCHEMBL177867; MolPort-004-955-368
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Seneciphylline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 333.38
Log P RDKit 1.11
Topological polar surface area (Å2) RDKit 76.07
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 24
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 3
Stereochemical complexity RDKit 0.17
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.56
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Seneciphylline
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 Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.41
Seneciphylline
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.84
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 No