IMPPAT Phytochemical information: 
Raucaffrinoline
Raucaffrinoline
Summary

SMILES: OC[C@@H]1[C@@H]2C[C@@H]3N([C@H]1C)[C@@H]1C2C(OC(=O)C)[C@]2(C3=Nc3c2cccc3)C1
InChI: InChI=1S/C21H24N2O3/c1-10-13(9-24)12-7-16-19-21(14-5-3-4-6-15(14)22-19)8-17(23(10)16)18(12)20(21)26-11(2)25/h3-6,10,12-13,16-18,20,24H,7-9H2,1-2H3/t10-,12-,13-,16-,17-,18?,20?,21+/m0/s1
InChIKey: XIMPCXFLDSKALH-GJBHJOTDSA-N
DeepSMILES: OC[C@@H][C@@H]C[C@@H]N[C@H]6C))[C@@H]C6COC=O)C)))[C@]C7=Ncc5cccc6))))))))C5
Scaffold Graph/Node/Bond level: c1ccc2c(c1)N=C1C3CC4CCN3C3CC12CC43
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4CCN3C3CC21CC43
Scaffold Graph level: C1CCC2C(C1)CC1C3CC4CCC3C3CC21CC43
Functional groups: CO; CN(C)C; COC(C)=O; cN=C(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ajmaline-sarpagine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
raucaffrinoline, Raucaffrinoline
External chemical identifiers:
CID:CID_56927714; ChEBI:CHEBI:63167
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Raucaffrinoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 2.05
Topological polar surface area (Å2) RDKit 62.13
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 8
Stereochemical complexity RDKit 0.38
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 13
Shape complexity RDKit 0.62
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
Raucaffrinoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 0
Ghose rule RDKit Passed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Good
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.83
Raucaffrinoline
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 Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.27
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