IMPPAT Phytochemical information: 
Thaliadine

Thaliadine
Summary

SMILES: COc1cc2-c3c4[C@H](Cc2cc1Oc1cc(OC)c(cc1C=O)OC)N(C)CCc4c(c(c3OC)OC)OC
InChI: InChI=1S/C30H33NO8/c1-31-9-8-18-26-20(31)10-16-11-25(39-21-14-24(35-4)22(33-2)12-17(21)15-32)23(34-3)13-19(16)27(26)29(37-6)30(38-7)28(18)36-5/h11-15,20H,8-10H2,1-7H3/t20-/m0/s1
InChIKey: CTIIMTXWHVNAII-FQEVSTJZSA-N
DeepSMILES: COccc-cc[C@H]Cc6cc%10OcccOC))ccc6C=O))))OC)))))))))))NC)CCc6ccc%10OC)))OC)))OC
Scaffold Graph/Node/Bond level: c1ccc(Oc2ccc3c(c2)CC2NCCc4cccc-3c42)cc1
Scaffold Graph/Node level: C1CCC(OC2CCC3C(C2)CC2NCCC4CCCC3C42)CC1
Scaffold Graph level: C1CCC(CC2CCC3C(C2)CC2CCCC4CCCC3C42)CC1
Functional groups: cOC; cOc; cC=O; CN(C)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aporphines
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tyrosine alkaloids
NP Classifier Class: Aporphine alkaloids
Synonymous chemical names:
thaliadine, Thaliadine, (s)-thaliadine
External chemical identifiers:
CID:CID_5321903; ZINC:ZINC000085835856
Chemical structure download


Thaliadine
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 535.59
Log P RDKit 5.1
Topological polar surface area (Å2) RDKit 84.92
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 0
Number of carbon atoms RDKit 30
Number of heavy atoms RDKit 39
Number of heteroatoms RDKit 9
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 1
Stereochemical complexity RDKit 0.03
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 19
Number of sp3 hybridized carbon atoms RDKit 11
Shape complexity RDKit 0.37
Number of rotatable bonds RDKit 9
Number of aliphatic carbocycles RDKit 1
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 5
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 5


Thaliadine
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 2
Lipinski’s rule of 5 RDKit Failed
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 0.35


Thaliadine
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 No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.51
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes