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

16(S)-Hydroxy-16,22-dihydroapparicine
Summary

SMILES: C/C=C/1CN2CCC1C(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=CCNCCC6CC)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:5374311
Chemical structure download


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 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 0.7286


16(S)-Hydroxy-16,22-dihydroapparicine
ADMET 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 -6.8
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 1.0
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