IMPPAT Phytochemical information: 
Indican (plant indican)

Indican (plant indican)
Summary

SMILES: OC[C@H]1O[C@@H](Oc2c[nH]c3c2cccc3)[C@@H]([C@H]([C@@H]1O)O)O
InChI: InChI=1S/C14H17NO6/c16-6-10-11(17)12(18)13(19)14(21-10)20-9-5-15-8-4-2-1-3-7(8)9/h1-5,10-19H,6H2/t10-,11-,12+,13-,14-/m1/s1
InChIKey: XVARCVCWNFACQC-RKQHYHRCSA-N
DeepSMILES: OC[C@H]O[C@@H]Occ[nH]cc5cccc6))))))))))[C@@H][C@H][C@@H]6O))O))O
Scaffold Graph/Node/Bond level: c1ccc2c(OC3CCCCO3)c[nH]c2c1
Scaffold Graph/Node level: C1CCC(OC2CNC3CCCCC32)OC1
Scaffold Graph level: C1CCC(CC2CCC3CCCCC32)CC1
Functional groups: CO; cO[C@@H](C)OC; c[nH]c
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
Synonymous chemical names:
indoxyl (indican), indican, indican (indoxyl beta-d glucoside), indican (indoxyl-beta-d-glucoside)
External chemical identifiers:
CID:CID_441564; ChEMBL:CHEMBL2063300; ChEBI:CHEBI:16700; ZINC:ZINC000004097614; FDASRS:N187WK1Y1J; SureChEMBL:SCHEMBL15756; MolPort-016-581-186
Chemical structure download


Indican (plant indican)
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 295.29
Log P RDKit -0.65
Topological polar surface area (Å2) RDKit 115.17
Number of hydrogen bond acceptors RDKit 6
Number of hydrogen bond donors RDKit 5
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 5
Stereochemical complexity RDKit 0.36
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 8
Number of sp3 hybridized carbon atoms RDKit 6
Shape complexity RDKit 0.43
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


Indican (plant indican)
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 0.513686


Indican (plant indican)
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 -8.18
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