tolinapant   Click here for help

GtoPdb Ligand ID: 12704

Synonyms: ASTX-660 | ASTX660 | compound 27 [PMID: 30091600]
Compound class: Synthetic organic
Comment: Tolinapant (ASTX660) is a non-peptidomimetic inhibitor of cIAP1/2 and XIAP, that was discovered using fragment-based drug design [1,5]. It is a Smac mimetic that induces TNFα-mediated necroptosis (inflammatory cell death) in cancer cells [4]. ASTX660 was designed for anticancer potential, and is active in in vitro and in vivo cancer models [2].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 2
Rotatable bonds 8
Topological polar surface area 80.64
Molecular weight 539.69
XLogP -0.39
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

SMILES / InChI / InChIKey
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Canonical SMILES C[C@@H]1CN(CC(=O)N2CC(C)(C)C3=NC(=C(CC4=CC=C(C=C4)F)C=C32)CO)[C@H](CN1)CN5CCOC[C@H]5C
Isomeric SMILES O=C(N1C=2C=C(CC3=CC=C(F)C=C3)C(CO)=NC2C(C1)(C)C)CN4C[C@H](NC[C@@H]4CN5[C@@H](COCC5)C)C
InChI InChI=1S/C30H42FN5O3/c1-20-14-35(25(13-32-20)15-34-9-10-39-18-21(34)2)16-28(38)36-19-30(3,4)29-27(36)12-23(26(17-37)33-29)11-22-5-7-24(31)8-6-22/h5-8,12,20-21,25,32,37H,9-11,13-19H2,1-4H3/t20-,21-,25-/m1/s1
InChI Key YCXOHEXZVKOGEV-DNRQZRRGSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
1-[6-[(4-fluorophenyl)methyl]-5-(hydroxymethyl)-3,3-dimethyl-2H-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-[[(3R)-3-methylmorpholin-4-yl]methyl]piperazin-1-yl]ethanone
International Nonproprietary Names Click here for help
INN number INN
11623 tolinapant
Synonyms Click here for help
ASTX-660 | ASTX660 | compound 27 [PMID: 30091600]
Database Links Click here for help
BindingDB Ligand 50450046
CAS Registry No. 1799328-86-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL4173974
GtoPdb PubChem SID 483123252
PubChem CID 118169620
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UniChem Compound Search for chemical match using the InChIKey YCXOHEXZVKOGEV-DNRQZRRGSA-N
UniChem Connectivity Search for chemical match using the InChIKey YCXOHEXZVKOGEV-DNRQZRRGSA-N