IMPPAT Phytochemical information: 
Sitsirikine
Sitsirikine
Summary

SMILES: C=C[C@H]1CN2CCc3c([C@@H]2C[C@@H]1[C@@H](C(=O)OC)CO)[nH]c1c3cccc1
InChI: InChI=1S/C21H26N2O3/c1-3-13-11-23-9-8-15-14-6-4-5-7-18(14)22-20(15)19(23)10-16(13)17(12-24)21(25)26-2/h3-7,13,16-17,19,22,24H,1,8-12H2,2H3/t13-,16-,17-,19-/m0/s1
InChIKey: JGKCGXVOATXMRM-UHEFJODHSA-N
DeepSMILES: C=C[C@H]CNCCcc[C@@H]6C[C@@H]%10[C@@H]C=O)OC)))CO))))))[nH]cc5cccc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CCCCN1CC3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CCCCC12
Scaffold Graph level: C1CCC2C(C1)CC1C3CCCCC3CCC21
Functional groups: C=CC; CN(C)C; COC(C)=O; CO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
sitsirikine
External chemical identifiers:
CID:CID_3050539; ZINC:ZINC000014710237; MolPort-039-338-621
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Sitsirikine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.45
Log P RDKit 2.67
Topological polar surface area (Å2) RDKit 65.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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
Sitsirikine
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 0.65
Sitsirikine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.72
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes