IMPPAT Phytochemical information: 
Raupine
Raupine
Summary

SMILES: OC[C@H]1[C@@H]2Cc3c4cc(O)ccc4[nH]c3[C@H]3[N+]2=C/C(=C/C)/[C@H]1C3
InChI: InChI=1S/C19H20N2O2/c1-2-10-8-21-17-7-14-13-5-11(23)3-4-16(13)20-19(14)18(21)6-12(10)15(17)9-22/h2-5,8,12,15,17-18,20,22H,6-7,9H2,1H3/p+1/b10-2-/t12-,15-,17+,18+/m1/s1
InChIKey: ADFKWOUMZCHRTD-QDHOPYFXSA-O
DeepSMILES: OC[C@H][C@@H]CccccO)ccc6[nH]c9[C@H][N+]%13=C/C=C/C))/[C@H]%17C6
Scaffold Graph/Node/Bond level: C=C1C=[N+]2C3Cc4c([nH]c5ccccc45)C2CC1C3
Scaffold Graph/Node level: CC1CN2C3CC1CC2C1NC2CCCCC2C1C3
Scaffold Graph level: CC1CC2C3CC1CC2C1CC2CCCCC2C1C3
Functional groups: CO; cO; c[nH]c; C/C=C(\C)C=[N+](C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
Synonymous chemical names:
Raupine, raupine
External chemical identifiers:
CID:CID_6436183
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Raupine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.39
Log P RDKit 2.51
Topological polar surface area (Å2) RDKit 59.26
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 3
Number of carbon atoms RDKit 19
Number of heavy atoms RDKit 23
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.21
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.42
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 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 6
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 6
Raupine
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 0.71
Raupine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -7.18
Number of PAINS structural alerts SwissADME 1
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