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: COC(=O)C(=CN(C)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: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 492.62
Log P RDKit 5.03
Topological polar surface area (Å2) RDKit 64.36
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 31
Number of heavy atoms RDKit 37
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 4
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.13
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.39
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 4
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 2
Number of aromatic rings RDKit 4
Total number of rings RDKit 8
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 8
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 0.366078
Roxburghine
ADME 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 -6.20
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 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