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CHEBI:3907 - coumermycin A1

ChEBI IDCHEBI:3907
ChEBI Namecoumermycin A1
Stars
ASCII Namecoumermycin A1
DefinitionA hydroxycoumarin antibiotic that is obtained from Streptomyces rishiriensis and exhibits potent antibacterial and anticancer activity.
Last Modified6 March 2015
DownloadsMolfile
FormulaC55H59N5O20
Net Charge0
Average Mass1110.092
Monoisotopic Mass1109.37534
SMILESCO[C@@H]1[C@@H](OC(=O)c2ccc(C)n2)[C@@H](O)[C@H](Oc2ccc3c(O)c(NC(=O)c4cnc(C(=O)Nc5c(O)c6ccc(O[C@@H]7OC(C)(C)[C@H](OC)[C@@H](OC(=O)c8ccc(C)n8)[C@H]7O)c(C)c6oc5=O)c4C)c(=O)oc3c2C)OC1(C)C
InChIInChI=1S/C55H59N5O20/c1-21-12-16-29(57-21)48(67)77-42-38(63)52(79-54(6,7)44(42)71-10)73-31-18-14-26-36(61)34(50(69)75-40(26)24(31)4)59-46(65)28-20-56-33(23(28)3)47(66)60-35-37(62)27-15-19-32(25(5)41(27)76-51(35)70)74-53-39(64)43(45(72-11)55(8,9)80-53)78-49(68)30-17-13-22(2)58-30/h12-20,38-39,42-45,52-53,56-58,61-64H,1-11H3,(H,59,65)(H,60,66)/t38-,39-,42+,43+,44-,45-,52-,53-/m1/s1
InChIKeyWTIJXIZOODAMJT-DHFGXMAYSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Streptomyces rishiriensis (ncbitaxon:68264) - PubMed (24079980)
Roles Classification
Biological Roles:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
DNA synthesis inhibitor  Any substance that inhibits the synthesis of DNA.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
topoisomerase IV inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase IV, which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
Hsp90 inhibitor  An EC 3.6.4.10 (non-chaperonin molecular chaperone ATPase) inhibitor that blocks the action of heat shock protein 90.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
coumermycin A1 (CHEBI:3907) has role antimicrobial agent (CHEBI:33281)
coumermycin A1 (CHEBI:3907) has role antineoplastic agent (CHEBI:35610)
coumermycin A1 (CHEBI:3907) has role bacterial metabolite (CHEBI:76969)
coumermycin A1 (CHEBI:3907) has role DNA synthesis inhibitor (CHEBI:59517)
coumermycin A1 (CHEBI:3907) has role Hsp90 inhibitor (CHEBI:63962)
coumermycin A1 (CHEBI:3907) has role topoisomerase IV inhibitor (CHEBI:53559)
coumermycin A1 (CHEBI:3907) is a aromatic amide (CHEBI:62733)
coumermycin A1 (CHEBI:3907) is a coumarins (CHEBI:23403)
coumermycin A1 (CHEBI:3907) is a glycoside (CHEBI:24400)
coumermycin A1 (CHEBI:3907) is a heteroarenecarboxylate ester (CHEBI:38064)
coumermycin A1 (CHEBI:3907) is a pyrroles (CHEBI:26455)
IUPAC Name 
(3-methyl-1H-pyrrole-2,4-diyl)bis[carbonylimino(4-hydroxy-8-methyl-2-oxo-2H-chromene-3,7-diyl)oxy(2R,3R,4S,5R)-3-hydroxy-5-methoxy-6,6-dimethyltetrahydro-2H-pyran-2,4-diyl] bis(5-methyl-1H-pyrrole-2-carboxylate)
INNs  Source
cumamicinaChemIDplus
coumamycinumChemIDplus
coumamycineChemIDplus
Synonyms  Source
CoumermycinKEGG COMPOUND
Notomycin A1ChemIDplus
NotomycinChemIDplus
NSC 107412ChemIDplus
Sugordomycin D-1aChemIDplus
Manual XrefsDatabases
C05073KEGG COMPOUND
C00002461KNApSAcK
D02333KEGG DRUG
Coumermycin_A1Wikipedia
Registry NumbersSources
Reaxys:5230975Reaxys
CAS:4434-05-3KEGG COMPOUND
CAS:4434-05-3ChemIDplus
Citations