RUBITECAN

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Search structure


Synonyms	9-nc 9-nitro-20(s)-camptothecin 9-nitro-20-(s)-camptothecin 9-nitrocamptothecin RFS 2000 RFS-2000 RFS2000 Rubitecan
Status
Molecule Category	UNKNOWN
UNII	H19C446XXB
EPA CompTox	DTXSID7046752


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

Structure


InChI Key	VHXNKPBCCMUMSW-FQEVSTJZSA-N
Smiles	CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2cc3c([N+](=O)[O-])cccc3nc2-1
InChI	InChI=1S/C20H15N3O6/c1-2-20(26)13-7-16-17-10(8-22(16)18(24)12(13)9-29-19(20)25)6-11-14(21-17)4-3-5-15(11)23(27)28/h3-7,26H,2,8-9H2,1H3/t20-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C20H15N3O6
Molecular Weight	393.36
AlogP	1.99
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	1.0
Number of Rotational Bond	2.0
Polar Surface Area	124.56
Molecular species	NEUTRAL
Aromatic Rings	3.0
Heavy Atoms	29.0

Bioactivity

Mechanism of Action	Action	Reference
DNA topoisomerase I inhibitor	INHIBITOR	EMA


Protein: DNA topoisomerase I Description: DNA topoisomerase 1 Organism : Homo sapiens P11387 ENSG00000198900

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Primary active transporter ATP-binding cassette ABCC subfamily	-	10200	-	-	-

Assay Description	Organism	Bioactivity	Reference
Cytotoxicity against human HeLa cells after 24 hrs by MTT assay	Homo sapiens	343.0 nM
Cytotoxicity against human Caco2 cells after 24 hrs by MTT assay	Homo sapiens	112.0 nM
Cytotoxicity against human A375 cells after 24 hrs by MTT assay	Homo sapiens	138.0 nM
Cytotoxicity against human Jurkat cells after 24 hrs by MTT assay	Homo sapiens	128.0 nM
Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay	Homo sapiens	479.0 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	37.5 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	18.63 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	2.282 %
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	-0.04 %		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	-0.11 %		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	-0.11 %		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	-0.04 %

Related Entries

Cross References

Resources	Reference
ChEBI	90225
ChEMBL	CHEMBL77305
DrugBank	DB06159
DrugCentral	2411
FDA SRS	H19C446XXB
PubChem	472335
SureChEMBL	SCHEMBL8640
ZINC	ZINC000003827362

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).