EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:157681 - tomaymycin

ChEBI IDCHEBI:157681
ChEBI Nametomaymycin
Stars
DefinitionA 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.
Last Modified25 January 2021
SubmitterMartin Larralde
DownloadsMolfile
FormulaC16H20N2O4
Net Charge0
Average Mass304.346
Monoisotopic Mass304.14231
SMILES[H]C(C)=C1CN2C(=O)c3cc(OC)c(O)cc3N[C@H](OC)[C@]2([H])C1
InChIInChI=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
InChIKeyUQVNRKBFAXNOGA-SWLSCSKDSA-N
Species of MetaboliteComponentSourceComments
Streptomyces achromogenes (ncbitaxon:67255) - PubMed (19270147)
Roles Classification
Biological Roles:
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.
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
(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
Manual XrefsDatabases
C00018843KNApSAcK
Registry NumbersSources
CAS:35050-55-6ChemIDplus
Citations