IMPPAT Phytochemical information: 
Calpurnine
Calpurnine
Summary

SMILES: O=C1CCC[C@H]2N1C[C@@H]1C[C@H]2CN2[C@H]1C[C@H](CC2)OC(=O)c1ccc[nH]1
InChI: InChI=1S/C20H27N3O3/c24-19-5-1-4-17-13-9-14(12-23(17)19)18-10-15(6-8-22(18)11-13)26-20(25)16-3-2-7-21-16/h2-3,7,13-15,17-18,21H,1,4-6,8-12H2/t13-,14-,15-,17+,18-/m0/s1
InChIKey: YFRYJFMFQOBOSY-YDRHNJASSA-N
DeepSMILES: O=CCCC[C@H]N6C[C@@H]C[C@H]6CN[C@H]6C[C@H]CC6))OC=O)cccc[nH]5
Scaffold Graph/Node/Bond level: O=C(OC1CCN2CC3CC(CN4C(=O)CCCC34)C2C1)c1ccc[nH]1
Scaffold Graph/Node level: OC(OC1CCN2CC3CC(CN4C(O)CCCC34)C2C1)C1CCCN1
Scaffold Graph level: CC(CC1CCC2CC3CC(CC4C(C)CCCC34)C2C1)C1CCCC1
Functional groups: CC(=O)N(C)C; CN(C)C; cC(=O)OC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Lupin alkaloids
ClassyFire Subclass: Sparteine, lupanine, and related alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Lysine alkaloids
NP Classifier Class: Quinolizidine alkaloids
Synonymous chemical names:
oroboidine, calpurnine
External chemical identifiers:
CID:CID_165547; ZINC:ZINC000006091647
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Calpurnine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 357.45
Log P RDKit 2.04
Topological polar surface area (Å2) RDKit 65.64
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.25
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 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 1
Total number of rings RDKit 5
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 4
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Calpurnine
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.822844
Calpurnine
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.09
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
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