CHEBI:66771 - polyketomycin

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ChEBI Name polyketomycin
ChEBI ID CHEBI:66771
Definition A carbohydrate-containing antibiotic isolated from the culture broth of Streptomyces sp.MK277-AF1. It exhibits potent antibacterial activity against several Gram-positive bacterial strains and is also found to be cytotoxic against a number of tumour cell lines.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information ZINC000001855333
Download Molfile XML SDF
Formula C44H48O18
Net Charge 0
Average Mass 864.84110
Monoisotopic Mass 864.28406
InChI InChI=1S/C44H48O18/c1-16-9-10-17(2)33(47)28(16)41(53)62-39-21(6)59-27(15-42(39,7)54)60-24-11-12-26(58-20(24)5)61-40-36(50)30(19(4)45)37(51)44(56)38(52)31-22(14-43(40,44)55)18(3)29-32(35(31)49)23(46)13-25(57-8)34(29)48/h9-10,13,20-21,24,26-27,39-40,45,47,49,54-56H,11-12,14-15H2,1-8H3/b30-19+/t20-,21+,24+,26+,27+,39-,40-,42-,43-,44-/m1/s1
InChIKey OWRCRVABZYJUES-FLJLGRLJSA-N
SMILES [H][C@@]1(CC[C@]([H])(O[C@H]2C[C@@](C)(O)[C@H](OC(=O)c3c(C)ccc(C)c3O)[C@H](C)O2)[C@@H](C)O1)O[C@@H]1C(=O)\C(=C(\C)O)C(=O)[C@@]2(O)C(=O)c3c(O)c4C(=O)C=C(OC)C(=O)c4c(C)c3C[C@@]12O
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain MK277 AF1 See: PubMed
Roles Classification
Biological Role(s): antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
(via carbohydrate-containing antibiotic )
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing polyketomycin (CHEBI:66771) has functional parent 3,6-dimethylsalicylic acid (CHEBI:70733)
polyketomycin (CHEBI:66771) has role antibacterial agent (CHEBI:33282)
polyketomycin (CHEBI:66771) has role antineoplastic agent (CHEBI:35610)
polyketomycin (CHEBI:66771) has role metabolite (CHEBI:25212)
polyketomycin (CHEBI:66771) is a p-quinones (CHEBI:25830)
polyketomycin (CHEBI:66771) is a benzoate ester (CHEBI:36054)
polyketomycin (CHEBI:66771) is a carbohydrate-containing antibiotic (CHEBI:23007)
polyketomycin (CHEBI:66771) is a carbopolycyclic compound (CHEBI:35294)
polyketomycin (CHEBI:66771) is a enol (CHEBI:33823)
polyketomycin (CHEBI:66771) is a glycoside (CHEBI:24400)
polyketomycin (CHEBI:66771) is a phenols (CHEBI:33853)
polyketomycin (CHEBI:66771) is a pyrans (CHEBI:26407)
polyketomycin (CHEBI:66771) is a tertiary α-hydroxy ketone (CHEBI:139592)
IUPAC Name
(2R,3S,6S)-2-methyl-6-{[(1S,3E,4aS,12aR)-4a,6,12a-trihydroxy-3-(1-hydroxyethylidene)-9-methoxy-11-methyl-2,4,5,7,10-pentaoxo-1,2,3,4,4a,5,7,10,12,12a-decahydrotetracen-1-yl]oxy}tetrahydro-2H-pyran-3-yl 2,6-dideoxy-4-O-(2-hydroxy-3,6-dimethylbenzoyl)-3-C-methyl-α-L-xylo-hexopyranoside
Registry Numbers Types Sources
200625-47-4 CAS Registry Number ChemIDplus
8184047 Reaxys Registry Number Reaxys
Citations
Daum M, Peintner I, Linnenbrink A, Frerich A, Weber M, Paululat T, Bechthold A (2009)
Organisation of the biosynthetic gene cluster and tailoring enzymes in the biosynthesis of the tetracyclic quinone glycoside antibiotic polyketomycin.
Chembiochem : a European journal of chemical biology 10, 1073-1083 [PubMed:19266534]
[show Abstract]
Paululat T, Zeeck A, Gutterer JM, Fiedler HP (1999)
Biosynthesis of polyketomycin produced by Streptomyces diastatochromogenes Tü 6028.
The Journal of antibiotics 52, 96-101 [PubMed:10344562]
[show Abstract]
Momose I, Chen W, Nakamura H, Naganawa H, Iinuma H, Takeuchi T (1998)
Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. II. Structure determination.
The Journal of antibiotics 51, 26-32 [PubMed:9531984]
[show Abstract]
Momose I, Chen W, Kinoshita N, Iinuma H, Hamada M, Takeuchi T (1998)
Polyketomycin, a new antibiotic from Streptomyces sp. MK277-AF1. I. Taxonomy, production, isolation, physico-chemical properties and biological activities.
The Journal of antibiotics 51, 21-25 [PubMed:9531983]
[show Abstract]
Last Modified
07 February 2018