ORTERONEL

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Search structure


Synonyms	Orteronel TAK-700
Status
Molecule Category	UNKNOWN
UNII	UE5K2FNS92


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

Structure


InChI Key	OZPFIJIOIVJZMN-SFHVURJKSA-N
Smiles	CNC(=O)c1ccc2cc([C@@]3(O)CCn4cncc43)ccc2c1
InChI	InChI=1S/C18H17N3O2/c1-19-17(22)14-3-2-13-9-15(5-4-12(13)8-14)18(23)6-7-21-11-20-10-16(18)21/h2-5,8-11,23H,6-7H2,1H3,(H,19,22)/t18-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C18H17N3O2
Molecular Weight	307.35
AlogP	2.04
Hydrogen Bond Acceptor	4.0
Hydrogen Bond Donor	2.0
Number of Rotational Bond	2.0
Polar Surface Area	67.15
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	23.0

Bioactivity

Mechanism of Action	Action	Reference
Cytochrome P450 17A1 inhibitor	INHIBITOR	PubMed


Protein: Cytochrome P450 17A1 Description: Steroid 17-alpha-hydroxylase/17,20 lyase Organism : Homo sapiens P05093 ENSG00000148795

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2	-	28000	-	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 17 Cytochrome P450 family 17A Cytochrome P450 17A1	-	19-270	40	-	-
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19	-	14000	-	-	-

Assay Description	Organism	Bioactivity	Reference
Inhibition of 17,20-lyase activity of Sprague-Dawley rat testicular microsomal CYP17A1 using [1,2-3H]-17a-hydroxyprogesterone as substrate after 15 mins by TLC analysis	Rattus norvegicus	48.0 nM
Inhibition of 17,20-lyase of recombinant human CYP17A1 using [1,2-3H]-17a-hydroxypregnenolone as substrate after 15 mins by TLC analysis	Homo sapiens	19.0 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	13.16 %
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	0.07 %
Inhibition of human CYP17A1	Homo sapiens	270.0 nM
Binding affinity human CYP17A1	Homo sapiens	40.0 nM

Cross References

Resources	Reference
ChEMBL	CHEMBL1921976
DrugBank	DB12066
FDA SRS	UE5K2FNS92
PDB	7D6
PubChem	9796590
SureChEMBL	SCHEMBL6126076
ZINC	ZINC000003943521

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).