PIRARUBICIN

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Search structure


Synonyms	Adriamycin, tetrahydropyranyl Pirarubicin Theprubicin Thp-adm
Status
Molecule Category	Free-form
ATC	L01DB08
UNII	D58G680W0G
EPA CompTox	DTXSID2046755


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

Structure


InChI Key	KMSKQZKKOZQFFG-YXRRJAAWSA-N
Smiles	COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O[C@@H]2CCCCO2)[C@H](C)O1
InChI	InChI=1S/C32H37NO12/c1-14-31(45-21-8-3-4-9-42-21)17(33)10-22(43-14)44-19-12-32(40,20(35)13-34)11-16-24(19)30(39)26-25(28(16)37)27(36)15-6-5-7-18(41-2)23(15)29(26)38/h5-7,14,17,19,21-22,31,34,37,39-40H,3-4,8-13,33H2,1-2H3/t14-,17-,19-,21+,22-,31+,32-/m0/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C32H37NO12
Molecular Weight	627.64
AlogP	1.55
Hydrogen Bond Acceptor	13.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	7.0
Polar Surface Area	204.3
Molecular species	BASE
Aromatic Rings	2.0
Heavy Atoms	45.0

Assay Description	Organism	Bioactivity	Reference
Tested for the cytotoxicity(1 hour incubation) against human colon tumor cell lines colon 4).	Homo sapiens	0.031
Tested for the cytotoxicity (continuous incubation) against human colon tumor cell lines (colon 4)determined by clonogenic assay.	Homo sapiens	0.004
Tested for the cytotoxicity(1 hour incubation) against human colon tumor cell lines (HT 29).	Homo sapiens	0.07
Tested for the cytotoxicity (continuous incubation) against human colon tumor cell lines (HT 29) determined by clonogenic assay.	Homo sapiens	0.006
Tested for the cytotoxicity(1 hour incubation) against L1210 leukemia cells.	Mus musculus	0.014
Tested for the cytotoxicity (continuous incubation) against L1210 leukemia cells determined by clonogenic assay.	Mus musculus	0.004
PubChem BioAssay. Increased HeLa cells with 2N DNA content-IC50. (Class of assay: confirmatory)	None	79.5 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (viability)-IC50. (Class of assay: confirmatory)	None	994.89 nM
PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmatory)	None	51.43 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory)	None	910.7 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory)	None	6.3 nM
PubChem BioAssay. Increased HeLa cells with 4N DNA content-IC50. (Class of assay: confirmatory)	None	80.63 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	-0.81 %
Antiproliferative activity against mouse MB49 cells assessed as reduction in cell viability after 72 hrs by WST-8 assay	Mus musculus	22.0 nM
Antiproliferative activity against C3H mouse MBT2 cells assessed as reduction in cell viability	Mus musculus	22.0 nM
Antiproliferative activity against mouse L5178Y cells assessed as reduction in cell viability	Mus musculus	23.0 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	0.4941 %
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	4.62 %		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	4.62 %

Related Entries

Cross References

Resources	Reference
ChEBI	94770
ChEMBL	CHEMBL2354444
DrugBank	DB11616
DrugCentral	2198
FDA SRS	D58G680W0G
PubChem	11296583
SureChEMBL	SCHEMBL8323
ZINC	ZINC000014087429

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).