IMPPAT Phytochemical information: 
19-Hydroxytabersonine
19-Hydroxytabersonine
Summary

SMILES: COC(=O)C1=C2Nc3c([C@@]42[C@@H]2[C@](C1)(C=CCN2CC4)C(O)C)cccc3
InChI: InChI=1S/C21H24N2O3/c1-13(24)20-8-5-10-23-11-9-21(19(20)23)15-6-3-4-7-16(15)22-17(21)14(12-20)18(25)26-2/h3-8,13,19,22,24H,9-12H2,1-2H3/t13?,19-,20-,21-/m0/s1
InChIKey: XDGRXQNYJMQLPU-VFZBCNBRSA-N
DeepSMILES: COC=O)C=CNcc[C@]5[C@@H][C@]C9)C=CCN6CC9))))))CO)C)))))cccc6
Scaffold Graph/Node/Bond level: C1=CC2CC=C3Nc4ccccc4C34CCN(C1)C24
Scaffold Graph/Node level: C1CCC2C(C1)NC1CCC3CCCN4CCC12C34
Scaffold Graph level: C1CCC2C(C1)CC1CCC3CCCC4CCC12C34
Functional groups: cNC(=C(C(=O)OC)C)C; CC=CC; CN(C)C; CO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Plumeran-type alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Aspidosperma type
Synonymous chemical names:
20-hydroxytabersonine, 19-hydroxytabersonine
External chemical identifiers:
CID:CID_443325; ChEBI:CHEBI:797
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
19-Hydroxytabersonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 2.19
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 4
Stereochemical complexity RDKit 0.19
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 11
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.48
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 3
Number of aliphatic rings RDKit 4
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
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
19-Hydroxytabersonine
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 0.63
19-Hydroxytabersonine
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 -6.87
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