TTNPB   Click here for help

GtoPdb Ligand ID: 2646

Synonyms: arotinoid acid
PDB Ligand
Compound class: Synthetic organic
Comment: TTNPB is a retinoic acid analogue. Like retinoic acid it is a selective RAR agonist. Synthetic polyaromatic retinoid compounds like TTNPB are known collectively as arotinoids.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 37.3
Molecular weight 348.21
XLogP 7.96
No. Lipinski's rules broken 1
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Canonical SMILES CC(=Cc1ccc(cc1)C(=O)O)c1ccc2c(c1)C(C)(C)CCC2(C)C
Isomeric SMILES C/C(=C\c1ccc(cc1)C(=O)O)/c1ccc2c(c1)C(C)(C)CCC2(C)C
InChI InChI=1S/C24H28O2/c1-16(14-17-6-8-18(9-7-17)22(25)26)19-10-11-20-21(15-19)24(4,5)13-12-23(20,2)3/h6-11,14-15H,12-13H2,1-5H3,(H,25,26)/b16-14+
1. Keidel S, LeMotte P, Apfel C. (1994)
Different agonist- and antagonist-induced conformational changes in retinoic acid receptors analyzed by protease mapping.
Mol Cell Biol, 14 (1): 287-98. [PMID:8264595]
2. Klaholz BP, Mitschler A, Moras D. (2000)
Structural basis for isotype selectivity of the human retinoic acid nuclear receptor.
J Mol Biol, 302 (1): 155-70. [PMID:10964567]
3. Nagy L, Thomázy VA, Shipley GL, Fésüs L, Lamph W, Heyman RA, Chandraratna RA, Davies PJ. (1995)
Activation of retinoid X receptors induces apoptosis in HL-60 cell lines.
Mol Cell Biol, 15 (7): 3540-51. [PMID:7791761]
4. Thacher SM, Vasudevan J, Chandraratna RA. (2000)
Therapeutic applications for ligands of retinoid receptors.
Curr Pharm Des, 6 (1): 25-58. [PMID:10637371]