doxorubicinol

CHEBI:133817 ·resolve ·ANTIMICROBIAL_UNSPECIFIED ·EXACT SEEDED

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. — 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:25830 CHEBI:25830
CHEBI:26191 CHEBI:26191
CHEBI:33853 CHEBI:33853
CHEBI:35315 CHEBI:35315
CHEBI:35618 CHEBI:35618
CHEBI:47779 CHEBI:47779
CHEBI:49322 CHEBI:49322
CHEBI:51286 CHEBI:51286

Chemical structure

Computed structure properties
Molecular formula	C27H31NO11
Charge	0
Average mass	545.541 Da
Monoisotopic mass	545.18971 Da
Source	ChEBI
InChIKey	NKZRZOVSJNSBFR-FEMMEMONSA-N

SMILES

COc1cccc2c1C(=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

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

Also called

(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 (EXACT_SYNONYM)— chebi
13-dihydrodoxorubicin (EXACT_SYNONYM)— chebi
Antibiotic 27706RP (EXACT_SYNONYM)— chebi
DOXOL (EXACT_SYNONYM)— chebi
adriamycinol (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:54193-28-1
hmdb:HMDB0041884
reaxys:6773847

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:133817`	doxorubicinol	`antibioticmech:chebi-782442fcab`	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.