IMPPAT Phytochemical information: 
Isatan B
Isatan B
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2cccc3)[C@@H](C(=O)[C@@H]1O)O
InChI: InChI=1S/C14H15NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-11,13-17,19H,6H2/t10-,11-,13-,14-/m1/s1
InChIKey: AHWQTWBZNABQTO-HBJVGIJOSA-N
DeepSMILES: OC[C@H]O[C@@H]Occ[nH]cc5cccc6))))))))))[C@@H]C=O)[C@@H]6O)))O
Scaffold Graph/Node/Bond level: O=C1CCOC(Oc2c[nH]c3ccccc23)C1
Scaffold Graph/Node level: OC1CCOC(OC2CNC3CCCCC32)C1
Scaffold Graph level: CC1CCCC(CC2CCC3CCCCC32)C1
Functional groups: CO; cO[C@@H](C)OC; c[nH]c; CC(=O)C
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Tryptophan alkaloids
NP Classifier Class: Simple indole alkaloids
Synonymous chemical names:
isatan b (indoxyl-5-ketogluconate), isatan b (indoxyl ketogluconate), isatan b
External chemical identifiers:
CID:CID_101529308; ZINC:ZINC000169692822
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
Isatan B
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 293.28
Log P RDKit -0.45
Topological polar surface area (Å2) RDKit 112.01
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 4
Number of carbon atoms RDKit 14
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 7
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 4
Stereochemical complexity RDKit 0.29
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 9
Number of sp3 hybridized carbon atoms RDKit 5
Shape complexity RDKit 0.36
Number of rotatable bonds RDKit 3
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 1
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 2
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
Isatan B
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 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 0.609918
Isatan B
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 -7.86
Number of PAINS structural alerts SwissADME 0
Number of Brenk structural alerts SwissADME 0
CYP1A2 inhibitor SwissADME Yes
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME No