IMPPAT Phytochemical information: 
Retusamine
Retusamine
Summary

SMILES: CCC12C(=O)OC3CC[N+]4(C3(O)C(=CC4)COC(=O)C(C2C)(OC1=O)C)C
InChI: InChI=1S/C19H26NO7/c1-5-18-11(2)17(3,27-16(18)23)14(21)25-10-12-6-8-20(4)9-7-13(19(12,20)24)26-15(18)22/h6,11,13,24H,5,7-10H2,1-4H3/q+1
InChIKey: ZNDNHSZHGPQSBN-UHFFFAOYSA-N
DeepSMILES: CCCC=O)OCCC[N+]C5O)C=CC5))COC=O)CC%14C))OC%15=O)))C)))))))C
Scaffold Graph/Node/Bond level: O=C1OCC2=CC[NH+]3CCC(OC(=O)C4CC1OC4=O)C23
Scaffold Graph/Node level: OC1OCC2CCN3CCC(OC(O)C4CC1OC4O)C23
Scaffold Graph level: CC1CCC2CCC3CCC(CC(C)C4CC1CC4C)C23
Functional groups: COC(=O)C; CC1=CC[N+](C)(C)C1(O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Tricarboxylic acids and derivatives
Synonymous chemical names:
retusamine
External chemical identifiers:
CID:CID_165551
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Retusamine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.42
Log P RDKit 0.28
Topological polar surface area (Å2) RDKit 99.13
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 5
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.74
Number of rotatable bonds RDKit 1
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 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4
Retusamine
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 Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.229345
Retusamine
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 -8.29
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 4
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes