IMPPAT Phytochemical information: 
N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
Summary

SMILES: OCC1OC(OC2(CC(=O)NC(C(=O)O)CC(=O)O)C(=O)Nc3c2cccc3)C(C(C1O)O)O
InChI: InChI=1S/C20H24N2O12/c23-7-11-14(27)15(28)16(29)18(33-11)34-20(8-3-1-2-4-9(8)22-19(20)32)6-12(24)21-10(17(30)31)5-13(25)26/h1-4,10-11,14-16,18,23,27-29H,5-7H2,(H,21,24)(H,22,32)(H,25,26)(H,30,31)
InChIKey: ANAVISFXAGVRIA-UHFFFAOYSA-N
DeepSMILES: OCCOCOCCC=O)NCC=O)O))CC=O)O)))))))C=O)Ncc5cccc6))))))))))CCC6O))O))O
Scaffold Graph/Node/Bond level: O=C1Nc2ccccc2C1OC1CCCCO1
Scaffold Graph/Node level: OC1NC2CCCCC2C1OC1CCCCO1
Scaffold Graph level: CC1CC2CCCCC2C1CC1CCCCC1
Functional groups: CO; COC(OC)C; CNC(C)=O; CC(=O)O; cNC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic acids and derivatives
ClassyFire Class: Carboxylic acids and derivatives
ClassyFire Subclass: Amino acids, peptides, and analogues
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple oxindole alkaloids
Synonymous chemical names:
n-[[3-(beta-d-glucopyranosyloxy)-2,3-dihydro-2-oxo-1h-indol-3-yl]acetyl]a+
External chemical identifiers:
CID:CID_25201824
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 484.41
Log P RDKit -2.92
Topological polar surface area (Å2) RDKit 232.18
Number of hydrogen bond acceptors RDKit 10
Number of hydrogen bond donors RDKit 8
Number of carbon atoms RDKit 20
Number of heavy atoms RDKit 34
Number of heteroatoms RDKit 14
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 7
Stereochemical complexity RDKit 0.35
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 10
Number of sp3 hybridized carbon atoms RDKit 10
Shape complexity RDKit 0.5
Number of rotatable bonds RDKit 8
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 2
Number of aliphatic rings RDKit 2
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 1
Total number of rings RDKit 3
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 3
N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 2
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Bad
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.176144
N-[[3-(b-D-Glucopyranosyloxy)-2,3-dihydro-2-oxo-1H-indol-3-yl]acetyl]aspartic acid
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Very soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -11.51
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 No