EMBL-EBI | Chemical Biology | ChEBI

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

CHEBI:40699 - anthramycin

Default Structure
ChEBI IDCHEBI:40699
ChEBI Nameanthramycin
Stars
DefinitionA 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.
Last Modified27 August 2020
DownloadsMolfile
FormulaC16H17N3O4
Net Charge0
Average Mass315.329
Monoisotopic Mass315.12191
SMILES[H][C@@]12CC(/C=C/C(N)=O)=CN1C(=O)c1ccc(C)c(O)c1N[C@@H]2O
InChIInChI=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
InChIKeyVGQOVCHZGQWAOI-YQRHFANHSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces refuineus subsp. thermotolerans (ncbitaxon:223297) - PubMed (17584616)
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
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.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
anthramycin (CHEBI:40699) has role alkylating agent (CHEBI:22333)
anthramycin (CHEBI:40699) has role antibacterial agent (CHEBI:33282)
anthramycin (CHEBI:40699) has role antineoplastic agent (CHEBI:35610)
anthramycin (CHEBI:40699) has role bacterial metabolite (CHEBI:76969)
anthramycin (CHEBI:40699) has role toxin (CHEBI:27026)
anthramycin (CHEBI:40699) is a enamide (CHEBI:51751)
anthramycin (CHEBI:40699) is a phenols (CHEBI:33853)
anthramycin (CHEBI:40699) is a primary amide (CHEBI:33256)
anthramycin (CHEBI:40699) is a pyrrolobenzodiazepine (CHEBI:131437)
IUPAC Name 
(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
INNs  Source
antramicinaWHO MedNet
antramycinWHO MedNet
antramycineWHO MedNet
antramycinumWHO MedNet
Synonyms  Source
anthramycinChemIDplus
Ro 5-9000ChemIDplus
Manual XrefsDatabases
ANTPDBeChem
AnthramycinWikipedia
CPD-18441MetaCyc
D02952KEGG DRUG
Registry NumbersSources
CAS:4803-27-4ChemIDplus
Citations