IMPPAT Phytochemical information: 
Calpaurine
Calpaurine
Summary

SMILES: OC1CC2C3CN4CCC(CC4C(C3)CN2C(=O)C1O)OC(=O)c1ccc[nH]1
InChI: InChI=1S/C20H27N3O5/c24-17-8-16-11-6-12(10-23(16)19(26)18(17)25)15-7-13(3-5-22(15)9-11)28-20(27)14-2-1-4-21-14/h1-2,4,11-13,15-18,21,24-25H,3,5-10H2
InChIKey: JCBFTVVDJBFDDD-UHFFFAOYSA-N
DeepSMILES: OCCCCCNCCCCC6CC%10)CN%12C=O)C%16O))))))))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: CO; CN(C)C; CC(=O)N(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:
calpaurine
External chemical identifiers:
CID:CID_190617
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Calpaurine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 389.45
Log P RDKit -0.02
Topological polar surface area (Å2) RDKit 106.1
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 3
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
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
Calpaurine
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 0.61
Calpaurine
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 -8.37
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes