upamostat   Click here for help

GtoPdb Ligand ID: 6497

Synonyms: WX-671
Compound class: Synthetic organic
Comment: Upamostat (WX-671) is an oral serine protease inhibitor prodrug. Its principal molecular target is plasminogen activator, urokinase (uPA; PLAU) [2]. The uPA system plays an important role in tumour invasion and metastasis. The active substance is WX-UK1.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 149.02
Molecular weight 629.32
XLogP 6.24
No. Lipinski's rules broken 2
Click here for help
Canonical SMILES CCOC(=O)N1CCN(CC1)C(=O)C(NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)C=NNO
Isomeric SMILES CCOC(=O)N1CCN(CC1)C(=O)[C@@H](NS(=O)(=O)c1c(cc(cc1C(C)C)C(C)C)C(C)C)Cc1cccc(c1)/C=N/NO
InChI InChI=1S/C32H47N5O6S/c1-8-43-32(39)37-14-12-36(13-15-37)31(38)29(17-24-10-9-11-25(16-24)20-33-35-40)34-44(41,42)30-27(22(4)5)18-26(21(2)3)19-28(30)23(6)7/h9-11,16,18-23,29,34-35,40H,8,12-15,17H2,1-7H3/b33-20+/t29-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Is prodrug? Yes
Active form WX-UK1
IUPAC Name Click here for help
ethyl 4-[(2S)-3-{3-[(1E)-[(hydroxyamino)imino]methyl]phenyl}-2-[2,4,6-tris(propan-2-yl)benzenesulfonamido]propanoyl]piperazine-1-carboxylate
International Nonproprietary Names Click here for help
INN number INN
9416 upamostat
Synonyms Click here for help
Database Links Click here for help
CAS Registry No. 590368-25-5 (source: PubChem)
GtoPdb PubChem SID 178103111
PubChem CID 56843330
Search Google for chemical match using the InChIKey CYCFEEXTLQGJEL-XEOXDSMQSA-N
Search Google for chemicals with the same backbone CYCFEEXTLQGJEL
Search PubMed clinical trials upamostat
Search PubMed titles upamostat
Search PubMed titles/abstracts upamostat
UniChem Compound Search for chemical match using the InChIKey CYCFEEXTLQGJEL-XEOXDSMQSA-N
UniChem Connectivity Search for chemical match using the InChIKey CYCFEEXTLQGJEL-XEOXDSMQSA-N