AVORALSTAT


Synonyms	Avoralstat BCX-4161
Status
Molecule Category	UNKNOWN
UNII	UX17773O15


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	TUWMKPVJGGWGNL-UHFFFAOYSA-N
Smiles	C=Cc1cc(C(=O)Nc2ccc(C(=N)N)cc2)c(-c2ccc(C(=O)NCC3CC3)nc2C(=O)O)cc1OC
InChI	InChI=1S/C28H27N5O5/c1-3-16-12-21(26(34)32-18-8-6-17(7-9-18)25(29)30)20(13-23(16)38-2)19-10-11-22(33-24(19)28(36)37)27(35)31-14-15-4-5-15/h3,6-13,15H,1,4-5,14H2,2H3,(H3,29,30)(H,31,35)(H,32,34)(H,36,37)

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C28H27N5O5
Molecular Weight	513.55
AlogP	3.77
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	10.0
Polar Surface Area	167.49
Molecular species	ZWITTERION
Aromatic Rings	3.0
Heavy Atoms	38.0

Bioactivity

Mechanism of Action	Action	Reference
Plasma kallikrein inhibitor	INHIBITOR	PubMed PubMed


Protein: Plasma kallikrein Description: Plasma kallikrein Organism : Homo sapiens P03952 ENSG00000164344

Assay Description	Organism	Bioactivity	Reference
Inhibition of purified human plasma kallikrein assessed as inhibition constant using H-D-Pro-Phe-Arg-pNA.2HCl as substrate measured after 3 mins by microplate reader analysis	Homo sapiens	0.26 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL4297502
DrugBank	DB12120
FDA SRS	UX17773O15
PDB	DJY
PubChem	86566678
SureChEMBL	SCHEMBL17513082

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).