tomaymycin

CHEBI:157681 ·resolve ·ANTIBACTERIAL ·EXACT SEEDED

A pyrrolobenzodiazepine that is (11aS)-2,3,5,10,11,11a-hexahydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine which is substituted at positions 2,5,7,8 and 11R by ethylidene, oxo, methoxy, hydroxy and methoxy groups, respectively. It is a natural product of Streptomyces achromogenes that binds covalently with guanine in the minor groove of DNA. It is an antitumoral compound which is active in ovarian, plasmacytoma, and leukemia cancer cell lines at nanomolar concentrations. — 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:33853 CHEBI:33853
CHEBI:35618 CHEBI:35618
CHEBI:78840 CHEBI:78840

Chemical structure

Computed structure properties
Molecular formula	C16H20N2O4
Charge	0
Average mass	304.346 Da
Monoisotopic mass	304.14231 Da
Source	ChEBI
InChIKey	UQVNRKBFAXNOGA-SWLSCSKDSA-N

SMILES

[H]C(C)=C1CN2C(=O)c3cc(OC)c(O)cc3N[C@H](OC)[C@]2([H])C1

InChI

InChI=1S/C16H20N2O4/c1-4-9-5-12-15(22-3)17-11-7-13(19)14(21-2)6-10(11)16(20)18(12)8-9/h4,6-7,12,15,17,19H,5,8H2,1-3H3/t12-,15+/m0/s1

Also called

(11R,11aS)-2-ethylidene-8-hydroxy-7,11-dimethoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:35050-55-6
knapsack:C00018843

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:157681`	tomaymycin	`antibioticmech:chebi-84471e8b48`	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.