ID: ALA2332887

Max Phase: Preclinical

Molecular Formula: C24H25F3N2O2

Molecular Weight: 430.47

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc2c(cc1-n1c(C(F)(F)F)nc3cc(C(=O)O)ccc31)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C24H25F3N2O2/c1-13-10-15-16(23(4,5)9-8-22(15,2)3)12-19(13)29-18-7-6-14(20(30)31)11-17(18)28-21(29)24(25,26)27/h6-7,10-12H,8-9H2,1-5H3,(H,30,31)

Standard InChI Key:  GBMUQLAGEWYKTJ-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: 430.47

Molecular Weight (Monoisotopic): 430.1868

AlogP: 6.40

#Rotatable Bonds: 2

Polar Surface Area: 55.12

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.61

CX Basic pKa: 0.85

CX LogP: 7.19

CX LogD: 3.85

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.51

Np Likeness Score: -0.54

References

1. Ohsawa F, Yamada S, Yakushiji N, Shinozaki R, Nakayama M, Kawata K, Hagaya M, Kobayashi T, Kohara K, Furusawa Y, Fujiwara C, Ohta Y, Makishima M, Naitou H, Tai A, Yoshikawa Y, Yasui H, Kakuta H..  (2013)  Mechanism of retinoid X receptor partial agonistic action of 1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-1H-benzotriazole-5-carboxylic acid and structural development to increase potency.,  56  (5): [PMID:23391145] [10.1021/jm400033f]

2. Takamura Y, Takahashi M, Nishii M, Shibahara O, Watanabe M, Fujihara M, Kakuta H..  (2019)  3H-Imidazo[4,5-b]pyridine-6-carboxylic acid derivatives as rexinoids with reduced teratogenicity.,  29  (15): [PMID:31160175] [10.1016/j.bmcl.2019.05.050]

3. Watanabe M,Fujihara M,Motoyama T,Kawasaki M,Yamada S,Takamura Y,Ito S,Makishima M,Nakano S,Kakuta H.  (2021)  Discovery of a "Gatekeeper" Antagonist that Blocks Entry Pathway to Retinoid X Receptors (RXRs) without Allosteric Ligand Inhibition in Permissive RXR Heterodimers.,  64  (1.0): [PMID:33356247] [10.1021/acs.jmedchem.0c01354]

Source

Source(1):

• Scientific Literature