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idarubicin   Click here for help

GtoPdb Ligand ID: 7083

Synonyms: Idamycin® | IMI-30 | Zavedos®
Approved drug PDB Ligand
idarubicin is an approved drug (FDA (1990))
Compound class: Natural product
Comment: Idarubicin is an anthracycline type antineoplastic drug.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 3
Topological polar surface area 176.61
Molecular weight 497.17
XLogP 0.65
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES OC1C(N)CC(OC1C)OC1CC(O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C
Isomeric SMILES O[C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C
InChI InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1
InChI Key XDXDZDZNSLXDNA-TZNDIEGXSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Natural product
Approved drug? Yes. US FDA (1990)
IUPAC Name Click here for help
(7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
International Nonproprietary Names Click here for help
INN number INN
5174 idarubicin
Synonyms Click here for help
Idamycin® | IMI-30 | Zavedos®
Database Links Click here for help
CAS Registry No. 58957-92-9
ChEBI CHEBI:42068
ChEMBL Ligand CHEMBL1117
DrugBank Ligand DB01177
DrugCentral Ligand 1414
GtoPdb PubChem SID 178103662
PubChem CID 42890
RCSB PDB Ligand DM5
Search Google for chemical match using the InChIKey XDXDZDZNSLXDNA-TZNDIEGXSA-N
Search Google for chemicals with the same backbone XDXDZDZNSLXDNA
Search PubMed clinical trials idarubicin
Search PubMed titles idarubicin
Search PubMed titles/abstracts idarubicin
UniChem Compound Search for chemical match using the InChIKey XDXDZDZNSLXDNA-TZNDIEGXSA-N
UniChem Connectivity Search for chemical match using the InChIKey XDXDZDZNSLXDNA-TZNDIEGXSA-N
Wikipedia Idarubicin