IMPPAT Phytochemical information: 
Azatoxin

Azatoxin
Summary

SMILES: COc1cc(cc(c1O)OC)[C@H]1N2C(=O)OC[C@@H]2Cc2c1[nH]c1c2cccc1
InChI: InChI=1S/C21H20N2O5/c1-26-16-7-11(8-17(27-2)20(16)24)19-18-14(9-12-10-28-21(25)23(12)19)13-5-3-4-6-15(13)22-18/h3-8,12,19,22,24H,9-10H2,1-2H3/t12-,19+/m0/s1
InChIKey: MIXLRUYCYZPSOQ-HXPMCKFVSA-N
DeepSMILES: COcccccc6O))OC))))[C@H]NC=O)OC[C@@H]5Ccc9[nH]cc5cccc6
Scaffold Graph/Node/Bond level: O=C1OCC2Cc3c([nH]c4ccccc34)C(c3ccccc3)N12
Scaffold Graph/Node level: OC1OCC2CC3C4CCCCC4NC3C(C3CCCCC3)N21
Scaffold Graph level: CC1CCC2CC3C4CCCCC4CC3C(C3CCCCC3)C12
Functional groups: cOC; cO; CN1CCOC1=O; c[nH]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: Carboline alkaloids
Synonymous chemical names:
azatoxin
External chemical identifiers:
CID:CID_125383; ChEMBL:CHEMBL275569; ZINC:ZINC000001626404; SureChEMBL:SCHEMBL18793659
Chemical structure download


Azatoxin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 380.4
Log P RDKit 3.36
Topological polar surface area (Å2) RDKit 84.02
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 28
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 2
Stereochemical complexity RDKit 0.1
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.29
Number of rotatable bonds RDKit 2
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
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


Azatoxin
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 0.73


Azatoxin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Moderately soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -6.53
Number of PAINS structural alerts SwissADME 1
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME Yes
CYP2C9 inhibitor SwissADME Yes
CYP2D6 inhibitor SwissADME Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME Yes


Azatoxin
Human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000411532TOP2A826
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.