IMPPAT Phytochemical information: 
[(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] 3,4,5-trimethoxybenzoate
[(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] 3,4,5-trimethoxybenzoate
Summary

SMILES: CC[C@H]1[C@@H]2C[C@@H]3N([C@@H]1O)[C@@H]1[C@H]2[C@@H](OC(=O)c2cc(OC)c(c(c2)OC)OC)[C@]2([C@H]3N(C)c3c2cccc3)C1
InChI: InChI=1S/C30H36N2O6/c1-6-16-17-13-20-26-30(18-9-7-8-10-19(18)31(26)2)14-21(32(20)28(16)33)24(17)27(30)38-29(34)15-11-22(35-3)25(37-5)23(12-15)36-4/h7-12,16-17,20-21,24,26-28,33H,6,13-14H2,1-5H3/t16-,17-,20-,21-,24-,26-,27+,28+,30+/m0/s1
InChIKey: JCRQPLRRHXVYJF-IBICUDAGSA-N
DeepSMILES: CC[C@H][C@@H]C[C@@H]N[C@@H]6O))[C@@H][C@H]6[C@@H]OC=O)cccOC))ccc6)OC)))OC))))))))[C@][C@H]7NC)cc5cccc6))))))))C5
Scaffold Graph/Node/Bond level: O=C(OC1C2C3CCN4C2CC12c1ccccc1NC2C4C3)c1ccccc1
Scaffold Graph/Node level: OC(OC1C2C3CCN4C2CC12C1CCCCC1NC2C4C3)C1CCCCC1
Scaffold Graph level: CC(CC1C2C3CCC4C2CC12C1CCCCC1CC2C4C3)C1CCCCC1
Functional groups: C[C@@H](O)N(C)C; cC(=O)OC; cOC; cN(C)C
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:
ajmalimine (21-trimethoxybenzoyl ajmaline), ajmalimine
External chemical identifiers:
CID:CID_131881743
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
[(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] 3,4,5-trimethoxybenzoate
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 520.63
Log P RDKit 3.45
Topological polar surface area (Å2) RDKit 80.7
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 38
Number of heteroatoms RDKit 8
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 9
Stereochemical complexity RDKit 0.3
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 13
Number of sp3 hybridized carbon atoms RDKit 17
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 7
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 5
Number of aliphatic rings RDKit 6
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 8
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 8
[(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] 3,4,5-trimethoxybenzoate
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 RDKit Passed
Number of Ghose rule violations RDKit 3
Ghose rule RDKit Failed
Veber rule RDKit Good
Egan rule RDKit Good
GSK 4/400 rule RDKit Bad
Pfizer 3/75 rule RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.58
[(1R,9R,10S,12R,13S,14R,16S,17S,18R)-13-ethyl-14-hydroxy-8-methyl-8,15-diazahexacyclo[14.2.1.01,9.02,7.010,15.012,17]nonadeca-2,4,6-trien-18-yl] 3,4,5-trimethoxybenzoate
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.66
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 Yes
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes