IMPPAT Phytochemical information: 
Indigo

Indigo
Summary

SMILES: O=C1c2ccccc2N=C1c1[nH]c2c(c1O)cccc2
InChI: InChI=1S/C16H10N2O2/c19-15-9-5-1-3-7-11(9)17-13(15)14-16(20)10-6-2-4-8-12(10)18-14/h1-8,17,19H
InChIKey: QQILFGKZUJYXGS-UHFFFAOYSA-N
DeepSMILES: O=Ccccccc6N=C9c[nH]ccc5O))cccc6
Scaffold Graph/Node/Bond level: O=C1C(c2cc3ccccc3[nH]2)=Nc2ccccc21
Scaffold Graph/Node level: OC1C2CCCCC2NC1C1CC2CCCCC2N1
Scaffold Graph level: CC1C2CCCCC2CC1C1CC2CCCCC2C1
Functional groups: cC1=NccC1=O; c[nH]c; cO
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organoheterocyclic compounds
ClassyFire Class: Indoles and derivatives
ClassyFire Subclass: Hydroxyindoles
NP Classifier Biosynthetic pathway: Alkaloids
NP Classifier Superclass: Anthranilic acid alkaloids
Synonymous chemical names:
indigo, Indigo, indigotin, indigo (indigotin)
External chemical identifiers:
CID:CID_10215; ChEMBL:CHEMBL35479; ZINC:ZINC000013783199; Molport-042-675-861|Molport-006-111-408|Molport-044-193-705|Molport-001-742-621
Chemical structure download


Indigo
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 262.27
Log P RDKit 3.19
Topological polar surface area (Å2) RDKit 65.45
Number of hydrogen bond acceptors RDKit 3
Number of hydrogen bond donors RDKit 2
Number of carbon atoms RDKit 16
Number of heavy atoms RDKit 20
Number of heteroatoms RDKit 4
Number of nitrogen atoms RDKit 2
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 0
Stereochemical complexity RDKit 0
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 16
Number of sp3 hybridized carbon atoms RDKit 0
Shape complexity RDKit 0
Number of rotatable bonds RDKit 1
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 2
Number of aromatic heterocycles RDKit 1
Number of aromatic rings RDKit 3
Total number of rings RDKit 4
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 0
Number of saturated rings RDKit 0
Number of Smallest Set of Smallest Rings (SSSR) RDKit 4


Indigo
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 Bad
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.706911


Indigo
ADME properties
Property nameToolProperty value
Bioavailability score SwissADME 0.55
Solubility class [ESOL] SwissADME Soluble
Solubility class [Silicos-IT] SwissADME Moderately soluble
Blood Brain Barrier permeation SwissADME Yes
Gastrointestinal absorption SwissADME High
Log Kp (Skin permeation, cm/s) SwissADME -5.96
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 Yes
CYP3A4 inhibitor SwissADME Yes
P-glycoprotein substrate SwissADME No