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CHEBI:40699 - anthramycin

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:
antibacterial agent  A substance (or active part thereof) that kills or slows the growth of bacteria.
toxin  Poisonous substance produced by a biological organism such as a microbe, animal or plant.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in 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.
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
antramycinumWHO MedNet
antramycinWHO MedNet
antramicinaWHO MedNet
antramycineWHO MedNet
Synonyms  Source
anthramycinChemIDplus
Ro 5-9000ChemIDplus
Manual XrefsDatabases
ANTPDBeChem
CPD-18441MetaCyc
D02952KEGG DRUG
AnthramycinWikipedia
Registry NumbersSources
CAS:4803-27-4ChemIDplus
Citations