CHEBI:138066 - nocamycin I

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ChEBI Name nocamycin I
ChEBI ID CHEBI:138066
Definition An organic heterotricyclic compound and tetramic acid derivative originally isolated from an unidentified oligosporic actinomycete strain (no. E864-861) and found to be active against both Gram-positive and Gram-negative anaerobic bacteria as well as some aerobic bacteria such as Streptococci. The methyl ester of nocamycin E.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H33NO9
Net Charge 0
Average Mass 503.543
Monoisotopic Mass 503.21553
InChI InChI=1S/C26H33NO9/c1-12(7-8-16(28)19-18(30)11-27-23(19)31)9-13(2)21-14(3)22-17(29)10-25(5)26(35-21,36-22)20(15(4)34-25)24(32)33-6/h7-9,13-15,20-22,28H,10-11H2,1-6H3,(H,27,31)/b8-7+,12-9+,19-16+/t13-,14-,15-,20-,21-,22+,25+,26+/m1/s1
InChIKey DTURANKMSHIDDI-GMYASLLUSA-N
SMILES [C@]12([C@@H]([C@](O[C@]3(O1)[C@H]([C@H](O[C@]3(CC2=O)C)C)C(=O)OC)([C@H](C)/C=C(\C)/C=C/C(=C/4\C(NCC4=O)=O)/O)[H])C)[H]
Roles Classification
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing nocamycin I (CHEBI:138066) has functional parent nocamycin E (CHEBI:141187)
nocamycin I (CHEBI:138066) has role antibacterial agent (CHEBI:33282)
nocamycin I (CHEBI:138066) has role bacterial metabolite (CHEBI:76969)
nocamycin I (CHEBI:138066) is a γ-lactam (CHEBI:74222)
nocamycin I (CHEBI:138066) is a enol (CHEBI:33823)
nocamycin I (CHEBI:138066) is a methyl ester (CHEBI:25248)
nocamycin I (CHEBI:138066) is a olefinic compound (CHEBI:78840)
nocamycin I (CHEBI:138066) is a organic heterotricyclic compound (CHEBI:26979)
nocamycin I (CHEBI:138066) is a spiroketal (CHEBI:72600)
nocamycin I (CHEBI:138066) is a tetramic acids (CHEBI:140155)
nocamycin I (CHEBI:138066) is conjugate acid of nocamycin I(1−) (CHEBI:141049)
Incoming nocamycin I(1−) (CHEBI:141049) is conjugate base of nocamycin I (CHEBI:138066)
IUPAC Name
methyl (2R,3S,3aS,5R,6R,7S,9aS)-5-[(2R,3E,5E,7E)-7-(2,4-dioxopyrrolidin-3-ylidene)-7-hydroxy-4-methylhepta-3,5-dien-2-yl]-2,6,9a-trimethyl-8-oxooctahydro-3a,7-epoxyfuro[3,2-b]oxocine-3-carboxylate
Synonyms Sources
(−)-nocamycin I ChEBI
Antibiotic BU 2313B ChEBI
BU 2313B ChEBI
Bu-2313B ChEBI
methyl (1S,2S,3R,5S,8S,9R,10R)-10-[(2R,3E,5E,7E)-7-(2,4-dioxopyrrolidin-3-ylidene)-7-hydroxy-4-methylhepta-3,5-dien-2-yl]-3,5,9-trimethyl-7-oxo-4,11,12-trioxatricyclo[6.3.1.01,5]dodecane-2-carboxylate IUPAC
Manual Xrefs Databases
CPD-18224 MetaCyc
US4181574 Patent
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Citations Waiting for Citations Types Sources
28818448 PubMed citation Europe PMC
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Last Modified
12 July 2018