CHEBI:90901 - protoasukamycin

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ChEBI Name protoasukamycin
ChEBI ID CHEBI:90901
Definition A polyketide that is (all-E)-7-(3-amino-4-hydroxyphenyl)hepta-2,4,6-trienoic acid in which the amino group has been acylated by an (all-E)-7-cyclohexylhepta-2,4,6-trienoyl group and in which the carboxy group has undergone formal condensation with the amino group of 2-amino-3-hydroxycyclopent-2-en-1-one to give the corresponding carboxamide. Protoasukamycin is an intermediate in the biosynthesis of asukamycin.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information ChemicalBook:CB5855401, ZINC000005854633
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Formula C31H34N2O5
Net Charge 0
Average Mass 514.613
Monoisotopic Mass 514.24677
InChI InChI=1S/C31H34N2O5/c34-26-19-18-24(15-7-2-4-11-17-30(38)33-31-27(35)20-21-28(31)36)22-25(26)32-29(37)16-10-3-1-6-12-23-13-8-5-9-14-23/h1-4,6-7,10-12,15-19,22-23,34-35H,5,8-9,13-14,20-21H2,(H,32,37)(H,33,38)/b3-1+,4-2+,12-6+,15-7+,16-10+,17-11+
InChIKey VBCLNKLOMFDNGC-JMAMMSEDSA-N
SMILES C1(=CC=C(C=C1NC(/C=C/C=C/C=C/C2CCCCC2)=O)/C=C/C=C/C=C/C(NC=3C(CCC3O)=O)=O)O
Roles Classification
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
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ChEBI Ontology
Outgoing protoasukamycin (CHEBI:90901) has role bacterial metabolite (CHEBI:76969)
protoasukamycin (CHEBI:90901) is a cyclic ketone (CHEBI:3992)
protoasukamycin (CHEBI:90901) is a enamide (CHEBI:51751)
protoasukamycin (CHEBI:90901) is a enol (CHEBI:33823)
protoasukamycin (CHEBI:90901) is a enone (CHEBI:51689)
protoasukamycin (CHEBI:90901) is a phenols (CHEBI:33853)
protoasukamycin (CHEBI:90901) is a polyketide (CHEBI:26188)
protoasukamycin (CHEBI:90901) is a secondary carboxamide (CHEBI:140325)
Incoming 4-hydroxyprotoasukamycin (CHEBI:90902) has functional parent protoasukamycin (CHEBI:90901)
IUPAC Name
(2E,4E,6E)-7-cyclohexyl-N-(2-hydroxy-5-{(1E,3E,5E)-7-[(2-hydroxy-5-oxocyclopent-1-en-1-yl)amino]-7-oxohepta-1,3,5-trien-1-yl}phenyl)hepta-2,4,6-trienamide
Synonym Source
protoasukamycin UniProt
Manual Xref Database
CPD-18765 MetaCyc
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Registry Number Type Source
21442509 Reaxys Registry Number Reaxys
Citations Types Sources
15038738 PubMed citation Europe PMC
20522559 PubMed citation Europe PMC
23100742 PubMed citation Europe PMC
23890006 PubMed citation SUBMITTER
Last Modified
07 March 2018