tomaymycin (CHEBI:157681)

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ChEBI Name	tomaymycin

ChEBI ID	CHEBI:157681

Definition	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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	Martin Larralde

Supplier Information

Download	Molfile XML SDF

Formula

C16H20N2O4

Net Charge

Average Mass

304.346

Monoisotopic Mass

304.14231

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

InChIKey

UQVNRKBFAXNOGA-SWLSCSKDSA-N

SMILES

[H]C(C)=C1CN2C(=O)C3=CC(OC)=C(O)C=C3N[C@H](OC)[C@]2([H])C1

Metabolite of Species	Details
Streptomyces achromogenes (NCBI:txid67255)	See: PubMed

Roles Classification
Biological Role(s):	antibacterial agent A substance (or active part thereof) that kills or slows the growth of bacteria. alkylating agent Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases. bacterial metabolite Any prokaryotic metabolite produced during a metabolic reaction in bacteria.

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	tomaymycin (CHEBI:157681) has role alkylating agent (CHEBI:22333) tomaymycin (CHEBI:157681) has role antibacterial agent (CHEBI:33282) tomaymycin (CHEBI:157681) has role antineoplastic agent (CHEBI:35610) tomaymycin (CHEBI:157681) has role bacterial metabolite (CHEBI:76969) tomaymycin (CHEBI:157681) is a aromatic ether (CHEBI:35618) tomaymycin (CHEBI:157681) is a olefinic compound (CHEBI:78840) tomaymycin (CHEBI:157681) is a phenols (CHEBI:33853) tomaymycin (CHEBI:157681) is a pyrrolobenzodiazepine (CHEBI:131437)

Incoming	(E)-tomaymycin (CHEBI:167317) is a tomaymycin (CHEBI:157681) (Z)-tomaymycin (CHEBI:167318) is a tomaymycin (CHEBI:157681)

IUPAC Name

(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

Registry Number	Type	Source
35050-55-6	CAS Registry Number	ChemIDplus

Last Modified

25 January 2021