CHEBI:133817 - doxorubicinol

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ChEBI Name doxorubicinol
ChEBI ID CHEBI:133817
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Bijay
Supplier Information
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Formula C27H31NO11
Net Charge 0
Average Mass 545.536
Monoisotopic Mass 545.18971
InChI InChI=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
InChIKey NKZRZOVSJNSBFR-FEMMEMONSA-N
SMILES C=1(O)C2=C(C(C3=C(C=CC=C3OC)C2=O)=O)C(O)=C4C1C[C@](C[C@@H]4O[C@H]5C[C@@H]([C@@H]([C@@H](O5)C)O)N)([C@H](CO)O)O
Roles Classification
Biological Role(s): drug metabolite

cardiotoxic agent
A role played by a chemical compound exihibiting 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.
(via anthracycline antibiotic )
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
13-dihydrodoxorubicin SUBMITTER
adriamycinol SUBMITTER
Antibiotic 27706RP ChemIDplus
DOXOL SUBMITTER
Manual Xref Database
HMDB0041884 HMDB
View more database links
Registry Numbers Types Sources
54193-28-1 CAS Registry Number ChemIDplus
6773847 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
03 November 2016