IMPPAT Phytochemical information: 
Roxburghine
Roxburghine
Summary

SMILES: COC(=O)C1=CN2CCc3c(C2(C2C1CC1N(C2)CCc2c1[nH]c1c2cccc1)C)[nH]c1c3cccc1
InChI: InChI=1S/C31H32N4O2/c1-31-24-17-34-13-11-20-18-7-3-5-9-25(18)32-28(20)27(34)15-22(24)23(30(36)37-2)16-35(31)14-12-21-19-8-4-6-10-26(19)33-29(21)31/h3-10,16,22,24,27,32-33H,11-15,17H2,1-2H3
InChIKey: SHKMVIVFLHPOSB-UHFFFAOYSA-N
DeepSMILES: COC=O)C=CNCCccC6CC%10CCNC6)CCcc6[nH]cc5cccc6))))))))))))))))C))[nH]cc5cccc6
Scaffold Graph/Node/Bond level: C1=CN2CCc3c([nH]c4ccccc34)C2C2CN3CCc4c([nH]c5ccccc45)C3CC12
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3C(CCN4CCC5C6CCCCC6NC5C34)CC12
Scaffold Graph level: C1CCC2C(C1)CC1C3CC4CCC5CCC6C7CCCCC7CC6C5C4CC3CCC21
Functional groups: CN(C)C; COC(=O)C(C)=CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Corynanthean-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
roxburghin, roxburghine d
External chemical identifiers:
CID:324225
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Roxburghine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 0
Log P RDKit 0
Topological polar surface area (Å2) RDKit
Number of hydrogen bond acceptors RDKit
Number of hydrogen bond donors RDKit
Number of carbon atoms RDKit
Number of heavy atoms RDKit
Number of heteroatoms RDKit
Number of nitrogen atoms RDKit
Number of sulfur atoms RDKit
Number of chiral carbon atoms RDKit
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit
Number of sp2 hybridized carbon atoms RDKit
Number of sp3 hybridized carbon atoms RDKit
Shape complexity RDKit
Number of rotatable bonds RDKit
Number of aliphatic carbocycles RDKit
Number of aliphatic heterocycles RDKit
Number of aliphatic rings RDKit
Number of aromatic carbocycles RDKit
Number of aromatic heterocycles RDKit
Number of aromatic rings RDKit
Total number of rings RDKit
Number of saturated carbocycles RDKit
Number of saturated heterocycles RDKit
Number of saturated rings RDKit
Number of Smallest Set of Smallest Rings (SSSR) RDKit
Roxburghine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.3661
Roxburghine
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.2
Number of PAINS structural alerts SwissADME 1.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes