6-[N-Ethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)amino]nicotinic acid

ID: ALA1221641

Chembl Id: CHEMBL1221641

Cas Number: 1246265-72-4

PubChem CID: 46933689

Max Phase: Preclinical

Molecular Formula: C22H28N2O2

Molecular Weight: 352.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(c1ccc2c(c1)C(C)(C)CCC2(C)C)c1ccc(C(=O)O)cn1

Standard InChI:  InChI=1S/C22H28N2O2/c1-6-24(19-10-7-15(14-23-19)20(25)26)16-8-9-17-18(13-16)22(4,5)12-11-21(17,2)3/h7-10,13-14H,6,11-12H2,1-5H3,(H,25,26)

Standard InChI Key:  RXCTZCYFGJAJCU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1221641

   6-[N-Ethyl(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)amino]nicotinic acid

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

Calculated Properties

Molecular Weight: 352.48

Molecular Weight (Monoisotopic): 352.2151

AlogP: 5.29

#Rotatable Bonds: 4

Polar Surface Area: 53.43

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.89

CX Basic pKa: 4.35

CX LogP: 4.95

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.81

Np Likeness Score: -0.32

References

1. Fujii S, Ohsawa F, Yamada S, Shinozaki R, Fukai R, Makishima M, Enomoto S, Tai A, Kakuta H..  (2010)  Modification at the acidic domain of RXR agonists has little effect on permissive RXR-heterodimer activation.,  20  (17): [PMID:20656484] [10.1016/j.bmcl.2010.07.012]

2. Ohsawa F, Morishita K, Yamada S, Makishima M, Kakuta H..  (2010)  Modification at the Lipophilic Domain of RXR Agonists Differentially Influences Activation of RXR Heterodimers.,  1  (9): [PMID:24900241] [10.1021/ml100184k]

3. Kakuta H, Yakushiji N, Shinozaki R, Ohsawa F, Yamada S, Ohta Y, Kawata K, Nakayama M, Hagaya M, Fujiwara C, Makishima M, Uno S, Tai A, Maehara A, Nakayama M, Oohashi T, Yasui H, Yoshikawa Y..  (2012)  RXR Partial Agonist CBt-PMN Exerts Therapeutic Effects on Type 2 Diabetes without the Side Effects of RXR Full Agonists.,  3  (5): [PMID:24900488] [10.1021/ml300055n]

4. 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]

5. Heck MC, Wagner CE, Shahani PH, MacNeill M, Grozic A, Darwaiz T, Shimabuku M, Deans DG, Robinson NM, Salama SH, Ziller JW, Ma N, van der Vaart A, Marshall PA, Jurutka PW..  (2016)  Modeling, Synthesis, and Biological Evaluation of Potential Retinoid X Receptor (RXR)-Selective Agonists: Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and 6-(Ethyl(5,5,8,8-tetrahydronaphthalen-2-yl)amino)nicotinic Acid (NEt-TMN).,  59  (19): [PMID:27592633] [10.1021/acs.jmedchem.6b00812]

6. Kawasaki M, Motoyama T, Yamada S, Watanabe M, Fujihara M, Kambe A, Nakano S, Kakuta H, Ito S..  (2023)  Ligand Screening System for the RXRα Heterodimer Using the Fluorescence RXR Agonist CU-6PMN.,  14  (3): [PMID:36923911] [10.1021/acsmedchemlett.2c00509]

Source

Source(1):

• Scientific Literature