IMPPAT Phytochemical information: 
trans-13-Cinnamoyloxylupanine
trans-13-Cinnamoyloxylupanine
Summary

SMILES: O=C(OC1N2CCCC[C@H]2C2CC1[C@H]1CCCC(=O)N1C2)/C=C/c1ccccc1
InChI: InChI=1S/C24H30N2O3/c27-22-11-6-10-21-19-15-18(16-26(21)22)20-9-4-5-14-25(20)24(19)29-23(28)13-12-17-7-2-1-3-8-17/h1-3,7-8,12-13,18-21,24H,4-6,9-11,14-16H2/b13-12+/t18?,19?,20-,21+,24?/m0/s1
InChIKey: MFZPBYKYOUMGKA-RUKNOJSZSA-N
DeepSMILES: O=COCNCCCC[C@H]6CCC%10[C@H]CCCC=O)N6C%10))))))))))))))))))/C=C/cccccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1C2CC(CN3C(=O)CCCC23)C2CCCCN21
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1C2CC(CN3C(O)CCCC23)C2CCCCN21
Scaffold Graph level: CC(CCC1CCCCC1)CC1C2CCCCC2C2CC3C(C)CCCC3C1C2
Functional groups: 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:
trans-13-cinnamoyloxylupanine
External chemical identifiers:
CID:CID_6427219
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
trans-13-Cinnamoyloxylupanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.52
Log P RDKit 3.45
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 24
Number of heavy atoms RDKit 29
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 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.58
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
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
trans-13-Cinnamoyloxylupanine
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 0.58
trans-13-Cinnamoyloxylupanine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.07
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 Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No