IMPPAT Phytochemical information: 
13-Tigloyloxylupanine
13-Tigloyloxylupanine
Summary

SMILES: C/C=C(/C(=O)OC1N2CCCC[C@H]2C2CC1[C@H]1CCCC(=O)N1C2)\C
InChI: InChI=1S/C20H30N2O3/c1-3-13(2)20(24)25-19-15-11-14(16-7-4-5-10-21(16)19)12-22-17(15)8-6-9-18(22)23/h3,14-17,19H,4-12H2,1-2H3/b13-3+/t14?,15?,16-,17+,19?/m0/s1
InChIKey: ZCUSRGNNIWPAKJ-JTIRAAQGSA-N
DeepSMILES: C/C=C/C=O)OCNCCCC[C@H]6CCC%10[C@H]CCCC=O)N6C%10)))))))))))))))))))\C
Scaffold Graph/Node/Bond level: O=C1CCCC2C3CC(CN12)C1CCCCN1C3
Scaffold Graph/Node level: OC1CCCC2C3CC(CN12)C1CCCCN1C3
Scaffold Graph level: CC1CCCC2C3CC4CCCCC4C(C3)CC12
Functional groups: C/C=C(\C)C(=O)OC(C)N(C)C; CC(=O)N(C)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:
13-tigloyloxylupanine
External chemical identifiers:
CID:CID_6427214
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
13-Tigloyloxylupanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 346.47
Log P RDKit 2.71
Topological polar surface area (Å2) RDKit 49.85
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 25
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
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 4
Number of sp3 hybridized carbon atoms RDKit 16
Shape complexity RDKit 0.8
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 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 4
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 4
13-Tigloyloxylupanine
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 0.56976
13-Tigloyloxylupanine
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 -6.40
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
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