1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)-1H-benzotriazole-5-carboxilic acid

ID: ALA2146901

Chembl Id: CHEMBL2146901

PubChem CID: 71461789

Max Phase: Preclinical

Molecular Formula: C22H25N3O2

Molecular Weight: 363.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc2c(cc1-n1nnc3cc(C(=O)O)ccc31)C(C)(C)CCC2(C)C

Standard InChI:  InChI=1S/C22H25N3O2/c1-13-10-15-16(22(4,5)9-8-21(15,2)3)12-19(13)25-18-7-6-14(20(26)27)11-17(18)23-24-25/h6-7,10-12H,8-9H2,1-5H3,(H,26,27)

Standard InChI Key:  QSRQAKVNYDAVIT-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA2146901

   1-(3,5,5,8,8-Pentamethyl-6,7-dihydronaphthalen-2-yl)benzotriazole-5-carboxylic 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: 363.46

Molecular Weight (Monoisotopic): 363.1947

AlogP: 4.78

#Rotatable Bonds: 2

Polar Surface Area: 68.01

Molecular Species: ACID

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.60

CX Basic pKa: ┄

CX LogP: 5.88

CX LogD: 2.54

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.71

Np Likeness Score: -0.66

References

1. 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]

2. 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]

3. 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]

4. 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