doxorubicin   Click here for help

GtoPdb Ligand ID: 7069

Synonyms: Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
Approved drug PDB Ligand
doxorubicin is an approved drug (FDA (1974), EMA (1996))
Compound class: Natural product
Comment: Doxorubicin is an anthracycline type anti-neoplastic drug.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 206.07
Molecular weight 543.17
XLogP -0.04
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES OCC(=O)C1(O)CC(OC2CC(N)C(C(O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
Isomeric SMILES OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
InChI InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChI Key AOJJSUZBOXZQNB-TZSSRYMLSA-N
Classification Click here for help
Compound class Natural product
Approved drug? Yes (FDA (1974), EMA (1996))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
Click to view more information about the WHO Model Lists of Essential Medicines.
IUPAC Name Click here for help
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
International Nonproprietary Names Click here for help
INN number INN
3005 doxorubicin
Synonyms Click here for help
Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
Database Links Click here for help
CAS Registry No. 23214-92-8
ChEBI CHEBI:28748
ChEMBL Ligand CHEMBL53463
DrugBank Ligand DB00997
DrugCentral Ligand 960
GtoPdb PubChem SID 178103648
Immunopaedia Search doxorubicin
LIPID MAPS LMPK13050001
PubChem CID 31703
RCSB PDB Ligand DM2
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UniChem Compound Search for chemical match using the InChIKey AOJJSUZBOXZQNB-TZSSRYMLSA-N
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Wikipedia Doxorubicin