IMPPAT Phytochemical information: 
Aristololactam-glucoside

Aristololactam-glucoside
Summary

SMILES: OC[C@H]1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)O)N1C(=O)c2c3c1cc1c(OC)cccc1c3c1c(c2)OCO1
InChI: InChI=1S/C23H21NO9/c1-30-13-4-2-3-9-10(13)5-12-16-11(6-14-21(17(9)16)32-8-31-14)22(29)24(12)23-20(28)19(27)18(26)15(7-25)33-23/h2-6,15,18-20,23,25-28H,7-8H2,1H3/t15-,18-,19+,20-,23+/m1/s1
InChIKey: GIDCUQKCIZAUKW-AUJACXKFSA-N
DeepSMILES: OC[C@H]O[C@@H][C@@H][C@H][C@@H]6O))O))O))NC=O)ccc5cccOC))cccc6c%10ccc%14)OCO5
Scaffold Graph/Node/Bond level: O=C1c2cc3c(c4c2c(cc2ccccc24)N1C1CCCCO1)OCO3
Scaffold Graph/Node level: OC1C2CC3OCOC3C3C4CCCCC4CC(C23)N1C1CCCCO1
Scaffold Graph level: CC1C2CC3CCCC3C3C4CCCCC4CC(C1C1CCCCC1)C23
Functional groups: CO; c1cOCO1; cC(=O)N([C@H](C)OC)c; cOC
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Alkaloids and derivatives
ClassyFire Class: Aristolactams
Synonymous chemical names:
aristolactum n-beta-glucoside
External chemical identifiers:
CID:CID_159819
Chemical structure download


Aristololactam-glucoside
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 455.42
Log P RDKit 0.49
Topological polar surface area (Å2) RDKit 138.15
Number of hydrogen bond acceptors RDKit 9
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 23
Number of heavy atoms RDKit 33
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 5
Stereochemical complexity RDKit 0.22
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 15
Number of sp3 hybridized carbon atoms RDKit 8
Shape complexity RDKit 0.35
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 3
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 3
Total number of rings RDKit 6
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 6


Aristololactam-glucoside
Drug-likeness properties
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 0
Ghose filter RDKit Passed
Veber filter RDKit Good
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.415812


Aristololactam-glucoside
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -8.25
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 1
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No