oleandomycin (Q1076248)

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chemical compound
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Language Label Description Also known as
English
oleandomycin
chemical compound

    Statements

    subclass of
    macrolides
    0 references
    polyketide
    0 references
    chemical structure
    Oleandomycin.png
    712 × 605; 14 KB
    0 references
    mass
    687.419376 dalton
    1 reference
    stated in
    PubChem
    PubChem CID
    19822
    language of work or name
    English
    title
    oleandomycin (English)
    retrieved
    21 September 2016
    chemical formula
    C₃₅H₆₁NO₁₂
    1 reference
    stated in
    PubChem
    PubChem CID
    19822
    language of work or name
    English
    title
    oleandomycin (English)
    retrieved
    21 September 2016
    canonical SMILES
    CC1CC(C(C(O1)OC2C(CC3(CO3)C(=O)C(C(C(C(OC(=O)C(C(C2C)OC4CC(C(C(O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
    1 reference
    stated in
    PubChem
    PubChem CID
    19822
    language of work or name
    English
    title
    oleandomycin (English)
    retrieved
    21 September 2016
    isomeric SMILES
    C[C@@H]1C[C@@H]([C@H]([C@@H](O1)O[C@H]2[C@H](C[C@@]3(CO3)C(=O)[C@@H]([C@H]([C@H]([C@H](OC(=O)[C@@H]([C@H]([C@@H]2C)O[C@H]4C[C@@H]([C@H]([C@@H](O4)C)O)OC)C)C)C)O)C)C)O)N(C)C
    0 references
    found in taxon
    Streptomyces antibioticus
    18 references
    stated in
    Streptomyces antibioticus contains at least three oleandomycin-resistance determinants, one of which shows similarity with proteins of the ABC-transporter superfamily.
    stated in
    Purification and characterization of an extracellular enzyme from Streptomyces antibioticus that converts inactive glycosylated oleandomycin into the active antibiotic
    stated in
    Interaction between ATP, oleandomycin and the OleB ATP-binding cassette transporter of Streptomyces antibioticus involved in oleandomycin secretion
    stated in
    Two glycosyltransferases and a glycosidase are involved in oleandomycin modification during its biosynthesis by Streptomyces antibioticus
    stated in
    Identification and antibacterial activity of a new oleandomycin derivative from Streptomyces antibioticus.
    stated in
    A cytochrome P450-like gene possibly involved in oleandomycin biosynthesis byStreptomyces antibioticus
    stated in
    Characterization of the ATPase activity of the N-terminal nucleotide binding domain of an ABC transporter involved in oleandomycin secretion by Streptomyces antibioticus
    stated in
    Biosynthesis of oleandomycin by Streptomyces antibioticus: influence of nutritional conditions and development of resistance.
    stated in
    Functional analysis of OleY L-oleandrosyl 3-O-methyltransferase of the oleandomycin biosynthetic pathway in Streptomyces antibioticus
    stated in
    Biosynthesis of the macrolide oleandomycin by Streptomyces antibioticus. Purification and kinetic characterization of an oleandomycin glucosyltransferase
    stated in
    Characterisation of a Streptomyces antibioticus gene encoding a type I polyketide synthase which has an unusual coding sequence.
    stated in
    Identification and expression of genes involved in biosynthesis of L-oleandrose and its intermediate L-olivose in the oleandomycin producer Streptomyces antibioticus
    stated in
    Analysis of a Streptomyces antibioticus chromosomal region involved in oleandomycin biosynthesis, which encodes two glycosyltransferases responsible for glycosylation of the macrolactone ring.
    stated in
    Interspecies complementation in Saccharopolyspora erythraea : elucidation of the function of oleP1, oleG1 and oleG2 from the oleandomycin biosynthetic gene cluster of Streptomyces antibioticus and generation of new erythromycin derivatives
    stated in
    A polyketide biosynthetic gene cluster from Streptomyces antibioticus includes a LysR-type transcriptional regulator
    stated in
    A second ABC transporter is involved in oleandomycin resistance and its secretion by Streptomyces antibioticus
    stated in
    Biosynthetic studies on oleandomycin by incorporation of the chemically synthesized aglycones
    stated in
    Resistance to oleandomycin in Streptomyces antibioticus, the producer organism.
    schematic
    Oleandomycin Synthesis 2.png
    1,670 × 1,077; 12 KB
    0 references
    Oleandomycin synthesis 1.png
    1,505 × 2,061; 44 KB
    0 references

    Identifiers

    ChemSpider ID
    18672
    1 reference
    stated in
    ChemSpider
    ChemSpider ID
    18672
    language of work or name
    English
    title
    (3S,5R,6S,7R,8R,11R,12S,13R,14S,15S)-12-[(2,6-dideoxy-3-O-methylhexopyranosyl)oxy]-6-hydroxy-5,7,8,11,13,15-hexamethyl-4,10-dioxo-1,9-dioxaspiro[2.13]hexadec-14-yl 3,4,6-trideoxy-3-(dimethylamino)hexo (English)
    retrieved
    21 September 2016
    Reaxys registry number
    74476
    0 references
    EC number
    223-495-7
    1 reference
    stated in
    ECHA Substance Infocard database
    ECHA Substance Infocard ID
    100.021.360
    retrieved
    27 December 2018
    title
    Oleandomycin (English)
    quotation
    CAS no.: 3922-90-5 (English)
    E number
    E704
    0 references
    ATC code
    J01FA05
    0 references
    MeSH descriptor ID
    D009827
    subject named as
    Oleandomycin
    0 references
    KEGG ID
    C01946
    0 references
    CAB ID
    206354
    1 reference
    stated in
    CAB Thesaurus
    retrieved
    6 April 2020
    DeCS ID
    27734
    0 references
     
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