4'-epidoxorubicin

CHEBI:47898 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

An anthracycline that is the 4'-epi-isomer of doxorubicin. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:139590 CHEBI:139590
CHEBI:139592 CHEBI:139592
CHEBI:25830 CHEBI:25830
CHEBI:35315 CHEBI:35315
CHEBI:47779 CHEBI:47779
CHEBI:48120 CHEBI:48120
CHEBI:49322 CHEBI:49322
CHEBI:63367 CHEBI:63367

Chemical structure

Computed structure properties
Molecular formula	C27H29NO11
Charge	0
Average mass	543.525 Da
Monoisotopic mass	543.17406 Da
Source	ChEBI
InChIKey	AOJJSUZBOXZQNB-VTZDEGQISA-N

SMILES

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1

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

Also called

epirubicin (INN)— chebi
(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 (EXACT_SYNONYM)— chebi
4'-Epiadriamycin (EXACT_SYNONYM)— chebi
Epiadriamycin (EXACT_SYNONYM)— chebi
epirubicina (EXACT_SYNONYM)— chebi
epirubicine (EXACT_SYNONYM)— chebi
epirubicinum (EXACT_SYNONYM)— chebi
pidorubicina (EXACT_SYNONYM)— chebi
pidorubicine (EXACT_SYNONYM)— chebi
pidorubicinum (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:56420-45-2
drugbank:DB00445
drugcentral:1030
kegg.compound:C11230
kegg.drug:D07901
lincs.smallmolecule:LSM-2078
patent:DE2510866
patent:US4058519
pdb-ccd:DM6
reaxys:1445812

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:33281 CHEBI:33281

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:47898`	4'-epidoxorubicin	`antibioticmech:chebi-45fa38c8cf`	2026-08-30

Mechanism summary

Mode of action: NUCLEIC_ACID_SYNTHESIS_INHIBITION host shared target — Assigned from ChEBI role CHEBI:50750 (EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor). ChEBI asserts the role on the compound. The target it names is one the host has too, so the mechanism is true but is not evidence of selectivity — see mode_of_action_target_scope. Not a curator's mechanistic review.

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.