daunorubicin   Click here for help

GtoPdb Ligand ID: 7063

Synonyms: Cerubidine® | daunomycin | FI-6339 | NDC-0082-4155 | RP-13057
Approved drug PDB Ligand
daunorubicin is an approved drug (FDA (1979), EMA (2018))
Comment: Daunorubicin is an anthracycline class chemotherapeutic for cancer treatment.
Daunorubicin is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019).
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 5
Rotatable bonds 4
Topological polar surface area 185.84
Molecular weight 527.18
XLogP 0.56
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)C(OC1CC(N)C(C(O1)C)O)CC(C2)(O)C(=O)C
Isomeric SMILES COc1cccc2c1C(=O)c1c(C2=O)c(O)c2c(c1O)[C@@H](O[C@H]1C[C@H](N)[C@@H]([C@@H](O1)C)O)C[C@](C2)(O)C(=O)C
InChI InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
InChI Key STQGQHZAVUOBTE-VGBVRHCVSA-N
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1979), EMA (2018))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
(8S,10S)-8-acetyl-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
International Nonproprietary Names Click here for help
INN number INN
2257 daunorubicin
Synonyms Click here for help
Cerubidine® | daunomycin | FI-6339 | NDC-0082-4155 | RP-13057
Database Links Click here for help
CAS Registry No. 20830-81-3
ChEBI CHEBI:41977
ChEMBL Ligand CHEMBL178
DrugBank Ligand DB00694
DrugCentral Ligand 786
GtoPdb PubChem SID 178103642
Immunopaedia Search daunorubicin
PubChem CID 30323
RCSB PDB Ligand DM1
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Wikipedia Daunorubicin