TRIAPINE

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Search structure


Synonyms	3-AP NSC-663249 OCX-0191 OCX-191 Ocx 191 PAN-811 Triapine
Status
Molecule Category	UNKNOWN
UNII	U4XIL4091C
EPA CompTox	DTXSID90893923


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

Structure


InChI Key	XMYKNCNAZKMVQN-NYYWCZLTSA-N
Smiles	NC(=S)N/N=C/c1ncccc1N
InChI	InChI=1S/C7H9N5S/c8-5-2-1-3-10-6(5)4-11-12-7(9)13/h1-4H,8H2,(H3,9,12,13)/b11-4+

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C7H9N5S
Molecular Weight	195.25
AlogP	-0.17
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	2.0
Polar Surface Area	89.32
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	13.0

Bioactivity

Mechanism of Action	Action	Reference
Ribonucleotide reductase inhibitor	INHIBITOR	PubMed PubMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	185	-	-	-
Unclassified protein	-	9078	-	388	-

Assay Description	Organism	Bioactivity	Reference
Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	Homo sapiens	260.0 nM
Antiproliferative activity against human SK-N-MC cells by MTT assay	Homo sapiens	310.0 nM
Antiproliferative activity against human SK-N-MC cells by MTT assay	Homo sapiens	540.0 nM
Antiproliferative activity against human SK-MN-C cells by MTT assay	Homo sapiens	660.0 nM
Antiproliferative activity against human SK-N-MC cells after 72 hrs by MTT assay	Homo sapiens	260.0 nM
Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged MitoNEET cytosolic domain (32 to 108 residues) expressed in Escherichia coli BL21 by Cheng-Prusoff analysis	Homo sapiens	388.0 nM
Inhibition of human RRM2 expressed in Escherichia coli BL21-codon plus(DE3) using [14C]-ADP as substrate after 3 mins by liquid scintillation counting method	Homo sapiens	185.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	-0.69 %
Antiproliferative activity against human PC3 cells assessed as reduction in cell proliferation incubated for 72 hrs by MTT assay	Homo sapiens	560.0 nM
Cytotoxicity against human A2780 cells incubated for 72 hrs by MTT assay	Homo sapiens	700.0 nM
Cytotoxicity against human SW480 cells incubated for 72 hrs by MTT assay	Homo sapiens	840.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	35.51 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	4.616 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.75 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.75 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	0.07 %
Antiproliferative activity against human PC-3 cells assessed as inhibition of cell proliferation measured after 72 hrs by MTT assay	Homo sapiens	560.0 nM
Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability incubated for 48 hrs by cell-titer-Glo luminescent cell viability assay	Homo sapiens	967.6 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL231616
DrugBank	DB11940
FDA SRS	U4XIL4091C
PharmGKB	PA165858618
SureChEMBL	SCHEMBL29370
ZINC	ZINC000006092213

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).