ID: ALA522998

Max Phase: Preclinical

Molecular Formula: C25H19N3

Molecular Weight: 361.45

Molecule Type: Small molecule

Representations

Synonyms (1): 1,1,1-Tris(3-Indolyl)Methane
Synonyms from Alternative Forms(1):

Canonical SMILES:  c1ccc2c(C(c3c[nH]c4ccccc34)c3c[nH]c4ccccc34)c[nH]c2c1

Standard InChI:  InChI=1S/C25H19N3/c1-4-10-22-16(7-1)19(13-26-22)25(20-14-27-23-11-5-2-8-17(20)23)21-15-28-24-12-6-3-9-18(21)24/h1-15,25-28H

Standard InChI Key:  AXZRNKFNIAOZEK-UHFFFAOYSA-N

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 361.45

Molecular Weight (Monoisotopic): 361.1579

AlogP: 6.31

#Rotatable Bonds: 3

Polar Surface Area: 47.37

Molecular Species: NEUTRAL

HBA: 0

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa:

CX Basic pKa:

CX LogP: 5.78

CX LogD: 5.78

Aromatic Rings: 6

Heavy Atoms: 28

QED Weighted: 0.33

Np Likeness Score: -0.03

References

1. Veluri R, Oka I, Wagner-Döbler I, Laatsch H..  (2003)  New indole alkaloids from the North Sea bacterium Vibrio parahaemolyticus Bio249.,  66  (11): [PMID:14640534] [10.1021/np030288g]

2. PubChem BioAssay data set, 

3. Roy S, Gajbhiye R, Mandal M, Pal C, Meyyapan A, Mukherjee J, Jaisankar P.  (2013)  Synthesis and antibacterial evaluation of 3,3-diindolylmethane derivatives,  [10.1007/s00044-013-0737-7]

4. Pillaiyar T, Köse M, Sylvester K, Weighardt H, Thimm D, Borges G, Förster I, von Kügelgen I, Müller CE..  (2017)  Diindolylmethane Derivatives: Potent Agonists of the Immunostimulatory Orphan G Protein-Coupled Receptor GPR84.,  60  (9): [PMID:28406627] [10.1021/acs.jmedchem.6b01593]

5. Dechering K; Duffey M.  (2022)  Replenishing the malaria drug discovery pipeline: Screening and hit evaluation of the MMV Hit Generation Library 1 (HGL1) against asexual blood stage Plasmodium falciparum ,using a nano luciferase reporter read-out,  [10.6019/CHEMBL4888484]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• MMV Malaria HGL