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CHEBI:53273 - esperamicin A1

ChEBI IDCHEBI:53273
ChEBI Nameesperamicin A1
Stars
ASCII Nameesperamicin A1
DefinitionA naturally occurring antibiotic and antitumor agent isolated from Actinomadura verrucosopora. Its chemical structure consists of a core bicyclo[7.3.1]tridecadiynene moiety containing a 1,5-diyn-3-ene as part of a ten-membered ring, a α,β-unsaturated ketone with a bridgehead double bond and an attached allylic trisulfide. This ring system is attached at one end by a trisaccharide moiety and at the opposite end by a 2-deoxy-L-fucose-anthranilate moiety. The trisaccharide consists of a hydroxyamino sugar which is connected to a isopropylamino sugar through a glycosidic linkage and a thiomethyl sugar through an NH‒O linkage.
Last Modified8 October 2009
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC59H80N4O22S4
Net Charge0
Average Mass1325.563
Monoisotopic Mass1324.41470
SMILES[H][C@@]1(O[C@@H]2O[C@H](C)[C@@H](NO[C@H]3C[C@H](O)[C@H](SC)[C@@H](C)O3)[C@H](O)[C@H]2O[C@H]2C[C@H](OC)[C@@H](NC(C)C)CO2)C#C/C=C\C#C[C@@]2(O)/C(=C/CSSSC)C1=C(NC(=O)OC)C(=O)[C@H]2O[C@H]1C[C@H](OC(=O)c2cc(OC)c(OC)cc2NC(=O)C(=C)OC)[C@H](O)[C@H](C)O1
InChIInChI=1S/C59H80N4O22S4/c1-28(2)60-36-27-77-43(25-39(36)73-8)83-52-50(66)47(63-85-45-24-37(64)53(86-12)31(5)79-45)29(3)80-57(52)82-38-18-16-14-15-17-20-59(71)34(19-21-88-89-87-13)46(38)48(62-58(70)76-11)51(67)54(59)84-44-26-42(49(65)30(4)78-44)81-56(69)33-22-40(74-9)41(75-10)23-35(33)61-55(68)32(6)72-7/h14-15,19,22-23,28-31,36-39,42-45,47,49-50,52-54,57,60,63-66,71H,6,21,24-27H2,1-5,7-13H3,(H,61,68)(H,62,70)/b15-14-,34-19+/t29-,30+,31-,36+,37+,38-,39+,42+,43+,44+,45+,47-,49-,50+,52-,53-,54-,57+,59-/m1/s1
InChIKeyLJQQFQHBKUKHIS-KSFFZXMPSA-N
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.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
esperamicin A1 (CHEBI:53273) has role alkylating agent (CHEBI:22333)
esperamicin A1 (CHEBI:53273) has role antineoplastic agent (CHEBI:35610)
esperamicin A1 (CHEBI:53273) is a esperamicin (CHEBI:53271)
IUPAC Name 
methyl {(1R,4Z,8R,12S,13E)-8-[(4,6-dideoxy-2-O-[2,4-dideoxy-3-O-methyl-4-(propan-2-ylamino)-α-L-threo-pentopyranosyl]-4-{[(2,6-dideoxy-4--methyl-4-thio-β-D-ribo-hexopyranosyl)oxy]amino}-β-D-glucopyranosyl)oxy]-12-[(2,6-dideoxy-3-O-{4,5-dimethoxy-2-[(2-methoxyprop-2-enoyl)amino]benzoyl}-α-L-lyxo-hexopyranosyl)oxy]-1-hydroxy-13-[2-(methyltrisulfanyl)ethylidene]-11-oxobicyclo[7.3.1]trideca-4,9-diene-2,6-diyn-10-yl}carbamate
Registry NumbersSources
CAS:99674-26-7ChemIDplus
Citations