IMPPAT Phytochemical information: 
13-Trans-cinnamoyloxylupanine
13-Trans-cinnamoyloxylupanine
Summary

SMILES: O=C(OC1CCN2[C@H](C1)C1CC(C2)[C@H]2N(C1)C(=O)CCC2)/C=C/c1ccccc1
InChI: InChI=1S/C24H30N2O3/c27-23-8-4-7-21-18-13-19(16-26(21)23)22-14-20(11-12-25(22)15-18)29-24(28)10-9-17-5-2-1-3-6-17/h1-3,5-6,9-10,18-22H,4,7-8,11-16H2/b10-9+/t18?,19?,20?,21-,22+/m0/s1
InChIKey: PUFYZCKVLOYPHL-MJPSBLOZSA-N
DeepSMILES: O=COCCCN[C@H]C6)CCCC6)[C@H]NC6)C=O)CCC6)))))))))))))))/C=C/cccccc6
Scaffold Graph/Node/Bond level: O=C(C=Cc1ccccc1)OC1CCN2CC3CC(CN4C(=O)CCCC34)C2C1
Scaffold Graph/Node level: OC(CCC1CCCCC1)OC1CCN2CC3CC(CN4C(O)CCCC34)C2C1
Scaffold Graph level: CC(CCC1CCCCC1)CC1CCC2CC3CC(CC4C(C)CCCC34)C2C1
Functional groups: c/C=C/C(=O)OC; CN(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-trans-cinnamoyloxylupanine
External chemical identifiers:
CID:CID_91748137
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
13-Trans-cinnamoyloxylupanine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.52
Log P RDKit 3.11
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
13-Trans-cinnamoyloxylupanine
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 0.583925
13-Trans-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 -6.39
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No