IMPPAT Phytochemical information: 
Rumberine
Rumberine
Summary

SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@@H]1N(C2)CC[C@]21C(=O)Nc1c2cc(O)cc1)C
InChI: InChI=1S/C21H24N2O5/c1-11-14-9-23-6-5-21(16-7-12(24)3-4-17(16)22-20(21)26)18(23)8-13(14)15(10-28-11)19(25)27-2/h3-4,7,10-11,13-14,18,24H,5-6,8-9H2,1-2H3,(H,22,26)/t11-,13-,14-,18-,21-/m0/s1
InChIKey: WDOSCDMZYXDQLB-NPJJOBTJSA-N
DeepSMILES: COC=O)C=CO[C@H][C@H][C@@H]6C[C@@H]NC6)CC[C@@]5C=O)Ncc5ccO)cc6))))))))))))))))C
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C12CCN1CC3COC=CC3CC12
Scaffold Graph/Node level: OC1NC2CCCCC2C12CCN1CC3COCCC3CC12
Scaffold Graph level: CC1CC2CCCCC2C12CCC1CC3CCCCC3CC12
Functional groups: COC(=O)C(=COC)C; CN(C)C; cNC(=O)C; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indolizidines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
rumberine, Rumberine
External chemical identifiers:
CID:CID_102094751; ZINC:ZINC000238768965
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Rumberine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 384.43
Log P RDKit 1.77
Topological polar surface area (Å2) RDKit 88.1
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.52
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 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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Rumberine
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 0.566787
Rumberine
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 -7.74
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 No
P-glycoprotein substrate SwissADME Yes