IMPPAT Phytochemical information: 
Ajmalicidine
Ajmalicidine
Summary

SMILES: COC(=O)n1c2ccccc2c2c1[C@@H]1C[C@@H]3C[C@@H](O)O[C@H]([C@H]3CN1CC2)C
InChI: InChI=1S/C21H26N2O4/c1-12-16-11-22-8-7-15-14-5-3-4-6-17(14)23(21(25)26-2)20(15)18(22)9-13(16)10-19(24)27-12/h3-6,12-13,16,18-19,24H,7-11H2,1-2H3/t12-,13+,16+,18-,19-/m0/s1
InChIKey: HVGMWXRXQCDMCS-ASVZHYIHSA-N
DeepSMILES: COC=O)ncccccc6cc9[C@@H]C[C@@H]C[C@@H]O)O[C@H][C@H]6CN%10CC%14)))))C
Scaffold Graph/Node/Bond level: c1ccc2c3c([nH]c2c1)C1CC2CCOCC2CN1CC3
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3COCCC3CC12
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: cn(C(=O)OC)c; C[C@@H](O)OC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Pyridoindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Yohimbine-like alkaloids
Synonymous chemical names:
amalicidine(1-carbomethoxy-17alpha-hydroxy-16-decarbomethoxy-16,17-dihydroajmalicine), ajmalicidine
External chemical identifiers:
CID:CID_101927009; ZINC:ZINC000238747793
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Ajmalicidine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 370.45
Log P RDKit 2.92
Topological polar surface area (Å2) RDKit 63.93
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 1
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 27
Number of heteroatoms RDKit 6
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.24
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 12
Shape complexity RDKit 0.57
Number of rotatable bonds RDKit 2
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 2
Number of saturated rings RDKit 2
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Ajmalicidine
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 0.772514
Ajmalicidine
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 -6.59
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 No