IMPPAT Phytochemical information: 
Ravifoline
Ravifoline
Summary

SMILES: C[C@@H]1CC[C@@]2(NC1)O[C@@H]1[C@H]([C@@H]2C)[C@@]2([C@@H](C1)[C@@H]1CC=C3[C@]([C@H]1CC2)(C)CC[C@@H](C3)O[C@@H]1OC[C@H]([C@@H]([C@H]1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)C
InChI: InChI=1S/C44H71NO14/c1-19-9-14-44(45-17-19)20(2)30-28(59-44)16-27-25-8-7-23-15-24(10-12-42(23,5)26(25)11-13-43(27,30)6)56-41-38(58-40-37(52)35(50)32(47)22(4)55-40)33(48)29(18-53-41)57-39-36(51)34(49)31(46)21(3)54-39/h7,19-22,24-41,45-52H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33+,34-,35-,36-,37-,38-,39+,40+,41+,42+,43+,44-/m1/s1
InChIKey: FMTSLKKSGAUWJE-GJZSKCTMSA-N
DeepSMILES: C[C@@H]CC[C@@]NC6))O[C@@H][C@H][C@@H]5C))[C@@][C@@H]C5)[C@@H]CC=C[C@][C@H]6CC%10)))C)CC[C@@H]C6)O[C@@H]OC[C@H][C@@H][C@H]6O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O)))))))O))O[C@@H]O[C@@H]C)[C@@H][C@H][C@H]6O))O))O))))))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=C2CC(OC3OCC(OC4CCCCO4)CC3OC3CCCCO3)CCC2C2CCC3C4CC5(CCCCN5)OC4CC3C2C1
Scaffold Graph/Node level: C1CCC2(CC3C(CC4C3CCC3C5CCC(OC6OCC(OC7CCCCO7)CC6OC6CCCCO6)CC5CCC34)O2)NC1
Scaffold Graph level: C1CCC(CC2CCC(CC3CCC4C(CCC5C4CCC4C6CC7(CCCCC7)CC6CC45)C3)C(CC3CCCCC3)C2)CC1
Functional groups: CC=C(C)C; CN[C@@](C)(C)OC; CO; CO[C@H](C)OC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Lipids and lipid-like molecules
ClassyFire Class: Steroids and steroid derivatives
ClassyFire Subclass: Steroidal glycosides
NP Classifier Biosynthetic pathway: Alkaloids|Terpenoids
NP Classifier Superclass: Pseudoalkaloids
NP Classifier Class: Steroidal alkaloids
Synonymous chemical names:
ravifoline
External chemical identifiers:
CID:101670644
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ravifoline
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 838.05
Log P RDKit 1.45
Topological polar surface area (Å2) RDKit 218.25
Number of hydrogen bond acceptors RDKit 15
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 44
Number of heavy atoms RDKit 59
Number of heteroatoms RDKit 15
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 25
Stereochemical complexity RDKit 0.57
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 42
Shape complexity RDKit 0.95
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 4
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 9
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 9
Number of saturated carbocycles RDKit 3
Number of saturated heterocycles RDKit 5
Number of saturated rings RDKit 8
Number of Smallest Set of Smallest Rings (SSSR) RDKit 9
Ravifoline
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 3
Lipinski’s rule of 5 filter RDKit Failed
Number of Ghose filter violations RDKit 3
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.1778