IMPPAT Phytochemical information: 
[(1R,9R,10S,12R,13S,14R,16S,17R,18R)-13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] acetate
[(1R,9R,10S,12R,13S,14R,16S,17R,18R)-13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] acetate
Summary

SMILES: CC[C@@H]1[C@@H](O)N2[C@@H]3[C@H]4[C@H]1C[C@H]2[C@H]1[C@@]([C@@H]4OC(=O)C)(C3)c2c(N1)cccc2
InChI: InChI=1S/C21H26N2O3/c1-3-11-12-8-15-18-21(13-6-4-5-7-14(13)22-18)9-16(23(15)20(11)25)17(12)19(21)26-10(2)24/h4-7,11-12,15-20,22,25H,3,8-9H2,1-2H3/t11-,12-,15-,16-,17+,18-,19+,20+,21+/m0/s1
InChIKey: VAOXSMUPPRUEKF-FJAUVILBSA-N
DeepSMILES: CC[C@@H][C@@H]O)N[C@@H][C@H][C@H]6C[C@H]6[C@H][C@@][C@@H]7OC=O)C))))C8)ccN5)cccc6
Scaffold Graph/Node/Bond level: c1ccc2c(c1)NC1C3CC4CCN3C3CC21CC43
Scaffold Graph/Node level: C1CCC2C(C1)NC1C3CC4CCN3C3CC21CC43
Scaffold Graph level: C1CCC2C(C1)CC1C3CC4CCC3C3CC21CC43
Functional groups: C[C@@H](O)N(C)C; CC(=O)OC; cNC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Ajmaline-sarpagine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type
Synonymous chemical names:
17-o-acetylnorajmaline
External chemical identifiers:
CID:CID_102420134; ZINC:ZINC000004102220
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1R,9R,10S,12R,13S,14R,16S,17R,18R)-13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] acetate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 354.45
Log P RDKit 2.1
Topological polar surface area (Å2) RDKit 61.8
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.43
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 7
Number of sp3 hybridized carbon atoms RDKit 14
Shape complexity RDKit 0.67
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 7
Number of saturated carbocycles RDKit 1
Number of saturated heterocycles RDKit 4
Number of saturated rings RDKit 5
Number of Smallest Set of Smallest Rings (SSSR) RDKit 7
[(1R,9R,10S,12R,13S,14R,16S,17R,18R)-13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] acetate
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 0.8
[(1R,9R,10S,12R,13S,14R,16S,17R,18R)-13-ethyl-14-hydroxy-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] acetate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -9.21
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes