ONX-0801   Click here for help

GtoPdb Ligand ID: 9590

Synonyms: BGC 945 | BGC-945 | N-[4-[2-Propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-l-γ-glutamyl-d-glutamic acid 1 [3] | ONX 0801
PDB Ligand
Compound class: Synthetic organic
Comment: ONX-0801 (originally named BGC 945) is a first-in-class small molecule inhibitor of thymidylate synthase (TS), that has been designed to accumulate differentially in cancer cells overexpressing the α-folate receptor [3] (FOLR1; P15328). Functionally, it resembles the TS inhibitors plevitrexed and raltitrexed. ONX-0801 is an oncology drug lead for epithelial tumours such as ovarian [1], lung and endometrial cancers, and mesothelioma tumours.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 14
Hydrogen bond donors 7
Rotatable bonds 17
Topological polar surface area 239.32
Molecular weight 647.22
XLogP 2.08
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES C#CCN(C1CCc2c1cc1c(=O)nc([nH]c1c2)CO)c1ccc(cc1)C(=O)NC(C(=O)O)CCC(=O)NC(C(=O)O)CCC(=O)O
Isomeric SMILES C#CCN([C@H]1CCc2c1cc1c(=O)nc([nH]c1c2)CO)c1ccc(cc1)C(=O)N[C@H](C(=O)O)CCC(=O)N[C@@H](C(=O)O)CCC(=O)O
InChI InChI=1S/C32H33N5O10/c1-2-13-37(25-10-5-18-14-24-21(15-20(18)25)30(43)36-26(16-38)33-24)19-6-3-17(4-7-19)29(42)35-23(32(46)47)8-11-27(39)34-22(31(44)45)9-12-28(40)41/h1,3-4,6-7,14-15,22-23,25,38H,5,8-13,16H2,(H,34,39)(H,35,42)(H,40,41)(H,44,45)(H,46,47)(H,33,36,43)/t22-,23+,25+/m1/s1
InChI Key NVHRBQOZEMFKLD-CUYJMHBOSA-N