IMPPAT Phytochemical information: 
Laudanosine
Laudanosine
Summary

SMILES: COc1cc(ccc1OC)CC1N(C)CCc2c1cc(OC)c(c2)OC
InChI: InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3
InChIKey: KGPAYJZAMGEDIQ-UHFFFAOYSA-N
DeepSMILES: COcccccc6OC)))))CCNC)CCcc6ccOC))cc6)OC
Scaffold Graph/Node/Bond level: c1ccc(CC2NCCc3ccccc32)cc1
Scaffold Graph/Node level: C1CCC(CC2NCCC3CCCCC32)CC1
Scaffold Graph level: C1CCC(CC2CCCC3CCCCC32)CC1
Functional groups: cOC; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Isoquinolines and derivatives
ClassyFire Subclass: Benzylisoquinolines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Isoquinoline alkaloids|Tetrahydroisoquinoline alkaloids
Synonymous chemical names:
(s)-laudanosine, (+) laudanosin, laudanosine, Laudanosine, (-) laudanosin, (+) laudanosine
External chemical identifiers:
CID:CID_15548; ChEMBL:CHEMBL1407; ChEBI:CHEBI:91599; SureChEMBL:SCHEMBL466529; MolPort-001-728-151
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Laudanosine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 357.45
Log P RDKit 3.49
Topological polar surface area (Å2) RDKit 40.16
Number of hydrogen bond acceptors RDKit 5
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 21
Number of heavy atoms RDKit 26
Number of heteroatoms RDKit 5
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.05
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 12
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.43
Number of rotatable bonds RDKit 6
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 2
Total number of rings RDKit 3
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 3
Laudanosine
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 0.79
Laudanosine
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Poorly soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.87
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 Yes
P-glycoprotein substrate SwissADME No
Laudanosine
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000299847CHRFAM7A800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.