IMPPAT Phytochemical information: 
Fruticosamine
Fruticosamine
Summary

SMILES: COC(=O)N1c2ccccc2[C@]23[C@@]41CC[C@]15[C@H]([C@@H]4O)C(=O)[C@H]2CN([C@H]31)CCC5
InChI: InChI=1S/C22H24N2O4/c1-28-19(27)24-14-6-3-2-5-12(14)22-13-11-23-10-4-7-20(18(22)23)8-9-21(22,24)17(26)15(20)16(13)25/h2-3,5-6,13,15,17-18,26H,4,7-11H2,1H3/t13-,15+,17+,18+,20-,21-,22+/m1/s1
InChIKey: UOVOJZZNYJYZNZ-MODNEBOESA-N
DeepSMILES: COC=O)Ncccccc6[C@][C@]9CC[C@][C@H][C@@H]6O))C=O)[C@H]8CN[C@H]%117)CCC9
Scaffold Graph/Node/Bond level: O=C1C2CC34CCC25CCCN2CC1C3(c1ccccc1N4)C25
Scaffold Graph/Node level: OC1C2CC34CCC25CCCN2CC1C3(C1CCCCC1N4)C25
Scaffold Graph level: CC1C2CC34CCC25CCCC2CC1C3(C1CCCCC1C4)C25
Functional groups: cN(C(=O)OC)C; CO; CC(=O)C; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aspidofractine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
fruticosamine, Fruticosamine
External chemical identifiers:
CID:CID_23279773; ChEMBL:CHEMBL96904; ZINC:ZINC000026666427
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Fruticosamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.44
Log P RDKit 1.7
Topological polar surface area (Å2) RDKit 70.08
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 22
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.32
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.64
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 5
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 8
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 5
Number of saturated heterocycles RDKit 2
Number of saturated rings RDKit 7
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
Fruticosamine
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 0.741912
Fruticosamine
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 -7.88
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes