IMPPAT Phytochemical information: 
Lotaustralin

Lotaustralin
Summary

SMILES: OC[C@H]1O[C@@H](O[C@@](C#N)(CC)C)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C11H19NO6/c1-3-11(2,5-12)18-10-9(16)8(15)7(14)6(4-13)17-10/h6-10,13-16H,3-4H2,1-2H3/t6-,7-,8+,9-,10+,11-/m1/s1
InChIKey: WEWBWVMTOYUPHH-QHAQEBJBSA-N
DeepSMILES: OC[C@H]O[C@@H]O[C@@]C#N))CC))C)))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: C1CCOCC1
Scaffold Graph/Node level: C1CCOCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CO; CO[C@@H](C)OC; CC#N
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
Lotaustralin, lotaustralin
External chemical identifiers:
CID:CID_441467; ChEBI:CHEBI:6542; ZINC:ZINC000004097529; FDASRS:P588137A94; SureChEMBL:SCHEMBL42924
Chemical structure download


Lotaustralin
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 261.27
Log P RDKit -1.5
Topological polar surface area (Å2) RDKit 123.17
Number of hydrogen bond acceptors RDKit 7
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 18
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.55
Number of sp hybridized carbon atoms RDKit 1
Number of sp2 hybridized carbon atoms RDKit 0
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 1
Number of rotatable bonds RDKit 4
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
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 1


Lotaustralin
Drug-likeness
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 0
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.485071


Lotaustralin
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -9.13
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 No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes