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CHEBI:133817 - doxorubicinol

ChEBI IDCHEBI:133817
ChEBI Namedoxorubicinol
Stars
DefinitionA member of the class of tetracenequinones that is the major metabolite of the anthracycline doxorubicin, a chemotherapeutic agent effective against a broad range of malignant neoplasms. It is thought to exhibit cardiotoxic properties.
Last Modified3 November 2016
SubmitterBijay
DownloadsMolfile
FormulaC27H31NO11
Net Charge0
Average Mass545.541
Monoisotopic Mass545.18971
SMILESCOc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)([C@@H](O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
InChIInChI=1S/C27H31NO11/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-,16-,17-,22+,27-/m0/s1
InChIKeyNKZRZOVSJNSBFR-FEMMEMONSA-N
Roles Classification
Biological Roles:
cardiotoxic agent  A role played by a chemical compound exhibiting itself through the ability to induce damage to the heart and cardiomyocytes.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
doxorubicinol (CHEBI:133817) has parent hydride tetracene (CHEBI:32600)
doxorubicinol (CHEBI:133817) has role cardiotoxic agent (CHEBI:50912)
doxorubicinol (CHEBI:133817) has role drug metabolite (CHEBI:49103)
doxorubicinol (CHEBI:133817) is a p-quinones (CHEBI:25830)
doxorubicinol (CHEBI:133817) is a aminoglycoside (CHEBI:47779)
doxorubicinol (CHEBI:133817) is a anthracycline antibiotic (CHEBI:49322)
doxorubicinol (CHEBI:133817) is a aromatic ether (CHEBI:35618)
doxorubicinol (CHEBI:133817) is a deoxy hexoside (CHEBI:35315)
doxorubicinol (CHEBI:133817) is a phenols (CHEBI:33853)
doxorubicinol (CHEBI:133817) is a polyol (CHEBI:26191)
doxorubicinol (CHEBI:133817) is a tetracenequinones (CHEBI:51286)
IUPAC Name 
(1S,3S)-3-[(1S)-1,2-dihydroxyethyl]-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
Synonyms  Source
13-dihydrodoxorubicinSUBMITTER
adriamycinolSUBMITTER
Antibiotic 27706RPChemIDplus
DOXOLSUBMITTER
Manual XrefsDatabases
HMDB0041884HMDB
Registry NumbersSources
Reaxys:6773847Reaxys
CAS:54193-28-1ChemIDplus
Citations