CHEBI:40699 - anthramycin

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ChEBI Name anthramycin
ChEBI ID CHEBI:40699
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H17N3O4
Net Charge 0
Average Mass 315.329
Monoisotopic Mass 315.12191
InChI InChI=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
InChIKey VGQOVCHZGQWAOI-YQRHFANHSA-N
SMILES [H][C@@]12CC(\C=C\C(N)=O)=CN1C(=O)C1=C(N[C@@H]2O)C(O)=C(C)C=C1
Metabolite of Species Details
Streptomyces refuineus subsp. thermotolerans (NCBI:txid223297) See: PubMed
Roles Classification
Biological Role(s): 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.
toxin
Poisonous substance produced by a biological organism such as a microbe, animal or plant.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Sources
antramicina WHO MedNet
antramycin WHO MedNet
antramycine WHO MedNet
antramycinum WHO MedNet
Synonyms Sources
anthramycin ChemIDplus
Ro 5-9000 ChemIDplus
Manual Xrefs Databases
ANT PDBeChem
Anthramycin Wikipedia
CPD-18441 MetaCyc
D02952 KEGG DRUG
View more database links
Registry Number Type Source
4803-27-4 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
15599 PubMed citation Europe PMC
1695729 PubMed citation Europe PMC
17134232 PubMed citation Europe PMC
17584616 PubMed citation Europe PMC
18512205 PubMed citation Europe PMC
21919439 PubMed citation Europe PMC
2342065 PubMed citation Europe PMC
2620069 PubMed citation Europe PMC
2720404 PubMed citation Europe PMC
27862776 PubMed citation Europe PMC
28373034 PubMed citation Europe PMC
3210245 PubMed citation Europe PMC
354779 PubMed citation Europe PMC
3973905 PubMed citation Europe PMC
5647054 PubMed citation Europe PMC
582801 PubMed citation Europe PMC
6736032 PubMed citation Europe PMC
6928034 PubMed citation Europe PMC
7672363 PubMed citation Europe PMC
7947769 PubMed citation Europe PMC
8343501 PubMed citation Europe PMC
8357813 PubMed citation Europe PMC
Last Modified
27 August 2020
General Comment
2020-08-27 The stereoconfiguration of the chiral centre at position 11 changes from 11R to 11S upon DNA binding according to PMID:7947769.