IMPPAT Phytochemical information: 
Tetrahydroalstonine
Tetrahydroalstonine
Summary

SMILES: COC(=O)C1=CO[C@H]([C@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1)C
InChI: InChI=1S/C21H24N2O3/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3/t12-,15-,16-,19-/m0/s1
InChIKey: GRTOGORTSDXSFK-DLLGKBFGSA-N
DeepSMILES: COC=O)C=CO[C@H][C@H][C@@H]6C[C@@H]NC6)CCcc6[nH]cc5cccc6))))))))))))))))C
Scaffold Graph/Node/Bond level: C1=CC2CC3c4[nH]c5ccccc5c4CCN3CC2CO1
Scaffold Graph/Node level: C1CCC2C(C1)NC1C2CCN2CC3COCCC3CC12
Scaffold Graph level: C1CCC2CC3C(CCC4C5CCCCC5CC34)CC2C1
Functional groups: COC(=O)C(=COC)C; CN(C)C; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Yohimbine alkaloids
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Corynanthe type|Yohimbine-like alkaloids
Synonymous chemical names:
Tetrahydroalstonine, tetrahydroalstonine, tatrahydroalstonine
External chemical identifiers:
CID:CID_72340; ChEMBL:CHEMBL498734; ChEBI:CHEBI:9479; ZINC:ZINC000053147420; SureChEMBL:SCHEMBL564502; MolPort-003-894-753
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Tetrahydroalstonine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 352.43
Log P RDKit 3.18
Topological polar surface area (Å2) RDKit 54.56
Number of hydrogen bond acceptors RDKit 4
Number of hydrogen bond donors RDKit 1
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 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 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 5
Tetrahydroalstonine
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
Tetrahydroalstonine
ADME 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 -6.50
Number of PAINS structural alerts SwissADME 1
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
Tetrahydroalstonine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000280155ADRA2A822
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.