ID: ALA246298

Max Phase: Preclinical

Molecular Formula: C19H18N2O2

Molecular Weight: 306.37

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc2[nH]cc(Cc3c[nH]c4ccc(OC)cc34)c2c1

Standard InChI:  InChI=1S/C19H18N2O2/c1-22-14-3-5-18-16(8-14)12(10-20-18)7-13-11-21-19-6-4-15(23-2)9-17(13)19/h3-6,8-11,20-21H,7H2,1-2H3

Standard InChI Key:  JTPGESPWPBXUEF-UHFFFAOYSA-N

Molecule Features

Natural Product: No

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: 306.37

Molecular Weight (Monoisotopic): 306.1368

AlogP: 4.26

#Rotatable Bonds: 4

Polar Surface Area: 50.04

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 3.95

CX LogD: 3.95

Aromatic Rings: 4

Heavy Atoms: 23

QED Weighted: 0.59

Np Likeness Score: -0.02

References

1. Pal C, Dey S, Mahato SK, Vinayagam J, Pradhan PK, Giri VS, Jaisankar P, Hossain T, Baruri S, Ray D, Biswas SM..  (2007)  Eco-friendly synthesis and study of new plant growth promoters: 3,3'-Diindolylmethane and its derivatives.,  17  (17): [PMID:17583501] [10.1016/j.bmcl.2007.06.025]

2. Maciejewska D, Rasztawicka M, Wolska I, Anuszewska E, Gruber B..  (2009)  Novel 3,3'-diindolylmethane derivatives: synthesis and cytotoxicity, structural characterization in solid state.,  44  (10): [PMID:19540023] [10.1016/j.ejmech.2009.05.011]

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. Köse M, Pillaiyar T, Namasivayam V, De Filippo E, Sylvester K, Ulven T, von Kügelgen I, Müller CE..  (2020)  An Agonist Radioligand for the Proinflammatory Lipid-Activated G Protein-Coupled Receptor GPR84 Providing Structural Insights.,  63  (5): [PMID:31721581] [10.1021/acs.jmedchem.9b01339]

Source

Source(1):

• Scientific Literature