AMRUBICIN

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Search structure


Synonyms	Amrubicin
Status
Molecule Category	Free-form
ATC	L01DB10
UNII	93N13LB4Z2


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

Structure


InChI Key	VJZITPJGSQKZMX-XDPRQOKASA-N
Smiles	CC(=O)[C@]1(N)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](O)[C@H](O)CO2)C1)C(=O)c1ccccc1C3=O
InChI	InChI=1S/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15+,16-,17-,25-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C25H25NO9
Molecular Weight	483.47
AlogP	0.63
Hydrogen Bond Acceptor	10.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	3.0
Polar Surface Area	176.61
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	35.0

Bioactivity

Mechanism of Action	Action	Reference
DNA topoisomerase II alpha inhibitor	INHIBITOR	PubMed


Protein: DNA topoisomerase II alpha Description: DNA topoisomerase 2-alpha Organism : Homo sapiens P11388 ENSG00000131747

Assay Description	Organism	Bioactivity	Reference
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	3.02 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	9.057 %
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	13.89 %		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	13.89 %
Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of VERO-E6 cells after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	330.0 nM		Determination of IC50 values for inhibition of SARS-CoV-2 induced cytotoxicity of VERO-E6 cells after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	330.0 nM

Related Entries

Cross References

Resources	Reference
ChEBI	135779
ChEMBL	CHEMBL1186894
DrugBank	DB06263
DrugCentral	202
FDA SRS	93N13LB4Z2
PubChem	3035016
SureChEMBL	SCHEMBL9140
ZINC	ZINC000003780800

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).