IMPPAT Phytochemical information: 
Neosarpagine
Neosarpagine
Summary

SMILES: OC[C@H]1[C@@H]2Cc3c([C@H]4N2CC([C@@H]1C4)C=C)[nH]c1c3cc(O)cc1
InChI: InChI=1S/C19H22N2O2/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/h2-5,10,12,15,17-18,20,22-23H,1,6-9H2/t10?,12-,15+,17-,18-/m0/s1
InChIKey: ZWEVQYKAXIUCLP-AMDDAFOPSA-N
DeepSMILES: OC[C@H][C@@H]Ccc[C@H]N6CC[C@@H]%10C6))C=C))))))[nH]cc5ccO)cc6
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCN1C(C3)C2
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CC2CC3CCN2C1C3
Scaffold Graph level: C1CCC2C(C1)CC1C3CC4CCC3C(C4)CC21
Functional groups: CO; CN(C)C; C=CC; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Macroline alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
neosarpagine, Neosarpagine
External chemical identifiers:
CID:CID_102075607
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Neosarpagine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 310.4
Log P RDKit 2.59
Topological polar surface area (Å2) RDKit 59.49
Number of hydrogen bond acceptors RDKit 3
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 5
Stereochemical complexity RDKit 0.26
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.47
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 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 3
Number of saturated rings RDKit 3
Number of Smallest Set of Smallest Rings (SSSR) RDKit 6
Neosarpagine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.747315
Neosarpagine
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 -6.54
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