anthramycin

CHEBI:40699 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A member of the class of pyrrolobenzodiazepines that is (11aS)-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine substituted at positions 2, 5, 8, 9 and 11R by a (1E)-3-amino-3-oxoprop-1-en-1-yl, oxo, methyl, hydroxy and hydroxy groups, respectively. It is a natural product isolated from Streptomyces refuineus subsp. thermotolerans. — 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:131437 CHEBI:131437
CHEBI:33256 CHEBI:33256
CHEBI:33853 CHEBI:33853
CHEBI:51751 CHEBI:51751

Chemical structure

Computed structure properties
Molecular formula	C16H17N3O4
Charge	0
Average mass	315.329 Da
Monoisotopic mass	315.12191 Da
Source	ChEBI
InChIKey	VGQOVCHZGQWAOI-YQRHFANHSA-N

SMILES

[H][C@@]12CC(/C=C/C(N)=O)=CN1C(=O)c1ccc(C)c(O)c1N[C@@H]2O

InChI

InChI=1S/C16H17N3O4/c1-8-2-4-10-13(14(8)21)18-15(22)11-6-9(3-5-12(17)20)7-19(11)16(10)23/h2-5,7,11,15,18,21-22H,6H2,1H3,(H2,17,20)/b5-3+/t11-,15+/m0/s1

Also called

antramicina (INN)— chebi
antramycin (INN)— chebi
antramycine (INN)— chebi
antramycinum (INN)— chebi
(2E)-3-[(11R,11aS)-9,11-dihydroxy-8-methyl-5-oxo-5,10,11,11a-tetrahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepin-2-yl]prop-2-enamide (EXACT_SYNONYM)— chebi
Ro 5-9000 (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:4803-27-4
kegg.drug:D02952
metacyc.compound:CPD-18441
pdb-ccd:ANT
wikipedia.en:Anthramycin

Activity roles

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

CHEBI:33282 CHEBI:33282

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:40699`	anthramycin	`antibioticmech:chebi-79bc47920b`	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.