IMPPAT Phytochemical information: 
16(S)-Hydroxy-16,22-dihydroapparicine
16(S)-Hydroxy-16,22-dihydroapparicine
Summary

SMILES: C/C=C/1\CN2CCC1C(C)(O)c1c(C2)c2c([nH]1)cccc2
InChI: InChI=1S/C18H22N2O/c1-3-12-10-20-9-8-15(12)18(2,21)17-14(11-20)13-6-4-5-7-16(13)19-17/h3-7,15,19,21H,8-11H2,1-2H3/b12-3+
InChIKey: PZYMRTAVKVZYMI-KGVSQERTSA-N
DeepSMILES: C/C=C\CNCCC\6CC)O)ccC8)cc[nH]5)cccc6
Scaffold Graph/Node/Bond level: C=C1CN2CCC1Cc1[nH]c3ccccc3c1C2
Scaffold Graph/Node level: CC1CN2CCC1CC1NC3CCCCC3C1C2
Scaffold Graph level: CC1CC2CCC1CC1CC3CCCCC3C1C2
Functional groups: C/C=C(\C)C; CN(C)C; CO; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Vallesaman alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
16(s)-hydroxy-16,22-dihydroapparicine
External chemical identifiers:
CID:CID_5374311
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
16(S)-Hydroxy-16,22-dihydroapparicine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 282.39
Log P RDKit 3.16
Topological polar surface area (Å2) RDKit 39.26
Number of hydrogen bond acceptors RDKit 2
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 18
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 3
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.11
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.44
Number of rotatable bonds RDKit 0
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 3
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
Total number of rings RDKit 5
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 5
16(S)-Hydroxy-16,22-dihydroapparicine
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 0.73
16(S)-Hydroxy-16,22-dihydroapparicine
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 -6.80
Number of PAINS structural alerts SwissADME 0
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