amrubicin

CHEBI:135779 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

A synthetic anthracycline antibiotic with molecular formula C25H25NO9. A specific inhibitor of topoisomerase II, it is used (particularly as the hydrochloride salt) in the treatment of cancer, especially lung cancer, where it is a prodrug for the active metabolite, ambrucinol. — 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:36141 CHEBI:36141
CHEBI:49322 CHEBI:49322
CHEBI:50994 CHEBI:50994
CHEBI:51270 CHEBI:51270
CHEBI:51867 CHEBI:51867

Chemical structure

Computed structure properties
Molecular formula	C25H25NO9
Charge	0
Average mass	483.473 Da
Monoisotopic mass	483.15293 Da
Source	ChEBI
InChIKey	VJZITPJGSQKZMX-XDPRQOKASA-N

SMILES

CC(=O)[C@]1(N)Cc2c(O)c3c(c(O)c2[C@@H](O[C@H]2C[C@H](O)[C@H](O)CO2)C1)C(=O)c1ccccc1C3=O

InChI

InChI=1S/C25H25NO9/c1-10(27)25(26)7-13-18(16(8-25)35-17-6-14(28)15(29)9-34-17)24(33)20-19(23(13)32)21(30)11-4-2-3-5-12(11)22(20)31/h2-5,14-17,28-29,32-33H,6-9,26H2,1H3/t14-,15+,16-,17-,25-/m0/s1

Also called

amrubicina (INN)— chebi
amrubicine (INN)— chebi
amrubicinum (INN)— chebi
(1S,3S)-3-acetyl-3-amino-5,12-dihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2-deoxy-β-D-erythro-pentopyranoside (EXACT_SYNONYM)— chebi
(7S,9S)-9-acetyl-9-amino-7-{[(2S,4S,5R)-4,5-dihydroxytetrahydro-2H-pyran-2-yl]oxy}-6,11-dihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione (EXACT_SYNONYM)— chebi
SM-5887 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:110267-81-7
drugcentral:202
kegg.drug:D08854
wikipedia.en:Amrubicin

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:135779`	amrubicin	`antibioticmech:chebi-4102939b86`	2026-08-30

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.