CHEBI:47898 - 4'-epidoxorubicin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name 4'-epidoxorubicin
ChEBI ID CHEBI:47898
Definition An anthracycline that is the 4'-epi-isomer of doxorubicin.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C27H29NO11
Net Charge 0
Average Mass 543.51930
Monoisotopic Mass 543.174
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
InChIKey AOJJSUZBOXZQNB-VTZDEGQISA-N
SMILES COc1cccc2C(=O)c3c(O)c4C[C@](O)(C[C@H](O[C@H]5C[C@H](N)[C@@H](O)[C@H](C)O5)c4c(O)c3C(=O)c12)C(=O)CO
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via anthracycline antibiotic )
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor
A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
(via anthracycline )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 4'-epidoxorubicin (CHEBI:47898) has functional parent doxorubicin (CHEBI:28748)
4'-epidoxorubicin (CHEBI:47898) has role antimicrobial agent (CHEBI:33281)
4'-epidoxorubicin (CHEBI:47898) has role antineoplastic agent (CHEBI:35610)
4'-epidoxorubicin (CHEBI:47898) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
4'-epidoxorubicin (CHEBI:47898) is a p-quinones (CHEBI:25830)
4'-epidoxorubicin (CHEBI:47898) is a aminoglycoside (CHEBI:47779)
4'-epidoxorubicin (CHEBI:47898) is a anthracycline (CHEBI:48120)
4'-epidoxorubicin (CHEBI:47898) is a anthracycline antibiotic (CHEBI:49322)
4'-epidoxorubicin (CHEBI:47898) is a deoxy hexoside (CHEBI:35315)
4'-epidoxorubicin (CHEBI:47898) is a monosaccharide derivative (CHEBI:63367)
4'-epidoxorubicin (CHEBI:47898) is a primary α-hydroxy ketone (CHEBI:139590)
4'-epidoxorubicin (CHEBI:47898) is a tertiary α-hydroxy ketone (CHEBI:139592)
4'-epidoxorubicin (CHEBI:47898) is conjugate acid of 4'-epidoxorubicinium (CHEBI:41983)
Incoming 4'-epidoxorubicinium (CHEBI:41983) is conjugate base of 4'-epidoxorubicin (CHEBI:47898)
IUPAC Name
(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-arabino-hexopyranoside
INN Source
epirubicin ChemIDplus
Synonyms Sources
4'-Epiadriamycin ChemIDplus
Epiadriamycin ChemIDplus
epirubicina ChemIDplus
epirubicine ChemIDplus
epirubicinum ChemIDplus
pidorubicina ChemIDplus
pidorubicine ChemIDplus
pidorubicinum ChemIDplus
Manual Xrefs Databases
1030 DrugCentral
C11230 KEGG COMPOUND
D07901 KEGG DRUG
DB00445 DrugBank
DE2510866 Patent
DM6 PDBeChem
LSM-2078 LINCS
US4058519 Patent
View more database links
Registry Numbers Types Sources
1445812 Reaxys Registry Number Reaxys
1445812 Beilstein Registry Number Beilstein
56420-45-2 CAS Registry Number KEGG COMPOUND
56420-45-2 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
11432615 PubMed citation Europe PMC
15821120 PubMed citation Europe PMC
16005104 PubMed citation Europe PMC
17604344 PubMed citation Europe PMC
18838875 PubMed citation Europe PMC
Last Modified
06 February 2018
General Comment
2011-08-01 An anthracycline antibiotic with antineoplastic actions similar to doxorubicin, 4'-epidoxorubicin is used as the hydrochloride salt for the treatment of leukaemias and lymphomas as well as the treatment of bladder, breast, and stomach cancers. It exerts its antitumor effects by interference with the synthesis and function of DNA.