IMPPAT Phytochemical information: 
Henningsamine
Henningsamine
Summary

SMILES: CC(=O)O[C@@H]1OCC=C2[C@H]3[C@@H]1[C@@H]1N(C(=O)C)c4c(C51[C@H](C3)N(C2)CC5)cccc4
InChI: InChI=1S/C23H26N2O4/c1-13(26)25-18-6-4-3-5-17(18)23-8-9-24-12-15-7-10-28-22(29-14(2)27)20(21(23)25)16(15)11-19(23)24/h3-7,16,19-22H,8-12H2,1-2H3/t16-,19-,20+,21-,22-,23?/m0/s1
InChIKey: ZRBMSORDEMTJNR-PDCDEOOLSA-N
DeepSMILES: CC=O)O[C@@H]OCC=C[C@H][C@@H]7[C@@H]NC=O)C))ccC5[C@H]C9)NC%11)CC5)))))cccc6
Scaffold Graph/Node/Bond level: C1=C2CN3CCC45c6ccccc6NC4C(COC1)C2CC35
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3COCCC4CN5CCC21C5CC43
Scaffold Graph level: C1CCC2C3CC4C(CCC45C4CCCCC4CC25)CC3C1
Functional groups: CO[C@@H](OC(C)=O)C; CC=C(C)C; cN(C(C)=O)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Strychnos alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type|Strychnos type
Synonymous chemical names:
henningsamine
External chemical identifiers:
CID:CID_101286227
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Henningsamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 394.47
Log P RDKit 2.23
Topological polar surface area (Å2) RDKit 59.08
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 29
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 5
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 6
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Henningsamine
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 0.54
Henningsamine
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 -7.77
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