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doxorubicin (Q18936)

From Wikidata
chemical compound
  • 14-hydroxydaunorubicine
  • 14-hydroxydaunomycin
  • (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
  • (8S-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
  • hydroxydaunorubicin
  • adriamycin
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Language Label Description Also known as
default for all languages
No label defined
    English
    doxorubicin
    chemical compound
    • 14-hydroxydaunorubicine
    • 14-hydroxydaunomycin
    • (1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside
    • (8S-cis)-10-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione
    • hydroxydaunorubicin
    • adriamycin

    Statements

    has use
    medication
    0 references
    chemical structure
    Doxorubicin.svg
    1,583 × 1,212; 4 KB
    0 references
    chemical formula
    C₂₇H₂₉NO₁₁
    1 reference
    stated in
    PubChem
    PubChem CID
    31703
    language of work or name
    English
    title
    doxorubicin (English)
    retrieved
    17 November 2016
    canonical SMILES
    CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
    1 reference
    stated in
    PubChem
    PubChem CID
    31703
    language of work or name
    English
    title
    doxorubicin (English)
    retrieved
    17 November 2016
    isomeric SMILES
    C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)CO)O)N)O
    1 reference
    stated in
    PubChem
    PubChem CID
    31703
    language of work or name
    English
    title
    doxorubicin (English)
    retrieved
    17 November 2016
    found in taxon
    Streptomyces peucetius
    34 references
    stated in
    Characterization of the Streptomyces peucetius ATCC 29050 genes encoding doxorubicin polyketide synthase
    stated in
    Expression of doxorubicin-daunorubicin resistance genes in different anthracycline-producing mutants of Streptomyces peucetius
    stated in
    Identification and characterization of the afsR homologue regulatory gene from Streptomyces peucetius ATCC 27952.
    stated in
    A bacterial analog of the mdr gene of mammalian tumor cells is present in Streptomyces peucetius, the producer of daunorubicin and doxorubicin
    stated in
    Exploration of geosmin synthase from Streptomyces peucetius ATCC 27952 by deletion of doxorubicin biosynthetic gene cluster
    stated in
    Enhancement of doxorubicin production by expression of structural sugar biosynthesis and glycosyltransferase genes in Streptomyces peucetius.
    stated in
    Self-resistance mechanism in Streptomyces peucetius: overexpression of drrA, drrB and drrC for doxorubicin enhancement
    stated in
    Isolation and genetic manipulation of the antibiotic down-regulatory gene, wblA ortholog for doxorubicin-producing Streptomyces strain improvement
    stated in
    Superoxide dismutase (SOD) genes in Streptomyces peucetius: effects of SODs on secondary metabolites production.
    stated in
    Enhancing macrolide production in Streptomyces by coexpressing three heterologous genes
    stated in
    Exploration of two epimerase homologs in Streptomyces peucetius ATCC 27952.
    stated in
    The DrrAB Efflux System of Streptomyces peucetius Is a Multidrug Transporter of Broad Substrate Specificity
    stated in
    Switching antibiotics production on and off in actinomycetes by an IclR family transcriptional regulator from Streptomyces peucetius ATCC 27952.
    stated in
    One-Pot Combinatorial Biosynthesis of Glycosylated Anthracyclines by Cocultivation of Streptomyces Strains Producing Aglycones and Nucleotide Deoxysugars
    stated in
    Complete genome sequence of Streptomyces peucetius ATCC 27952, the producer of anticancer anthracyclines and diverse secondary metabolites
    stated in
    Implication of orphan histidine kinase (OhkAsp) in biosynthesis of doxorubicin and daunorubicin in Streptomyces peucetius ATCC 27952
    stated in
    Isolation and characterization of a gene from Streptomyces sp. strain C5 that confers the ability to convert daunomycin to doxorubicin on Streptomyces lividans TK24
    stated in
    Expression and characterization of DrrA and DrrB proteins of Streptomyces peucetius in Escherichia coli: DrrA is an ATP binding protein
    stated in
    Minimal Streptomyces sp. strain C5 daunorubicin polyketide biosynthesis genes required for aklanonic acid biosynthesis
    stated in
    Production of the antitumor drug epirubicin (4′-epidoxorubicin) and its precursor by a genetically engineered strain of Streptomyces peucetius
    stated in
    The Streptomyces peucetius dpsY anddnrX Genes Govern Early and Late Steps of Daunorubicin and Doxorubicin Biosynthesis
    stated in
    Purification, properties, and characterization of recombinant Streptomyces sp. strain C5 DoxA, a cytochrome P-450 catalyzing multiple steps in doxorubicin biosynthesis
    stated in
    Doxorubicin overproduction in Streptomyces peucetius: cloning and characterization of the dnrU ketoreductase and dnrV genes and the doxA cytochrome P-450 hydroxylase gene
    stated in
    Glucose kinases from Streptomyces peucetius var. caesius.
    stated in
    NdgR, an IclR-like regulator involved in amino-acid-dependent growth, quorum sensing, and antibiotic production in Streptomyces coelicolor
    stated in
    Precursor for biosynthesis of sugar moiety of doxorubicin depends on rhamnose biosynthetic pathway in Streptomyces peucetius ATCC 27952.
    stated in
    Identification of the duplicated genes for S-adenosyl-l-methionine synthetase (metK1-sp and metK2-sp) in Streptomyces peucetius var. caesius ATCC 27952.
    stated in
    Improvement in doxorubicin productivity by overexpression of regulatory genes in Streptomyces peucetius
    stated in
    Enhanced doxorubicin production by Streptomyces peucetius using a combination of classical strain mutation and medium optimization
    stated in
    The Streptomyces peucetius drrC gene encodes a UvrA-like protein involved in daunorubicin resistance and production
    stated in
    Interspecies DNA microarray analysis identifies WblA as a pleiotropic down-regulator of antibiotic biosynthesis in Streptomyces
    stated in
    Genome analyses of Streptomyces peucetius ATCC 27952 for the identification and comparison of cytochrome P450 complement with other Streptomyces
    stated in
    Limitations in doxorubicin production from Streptomyces peucetius
    stated in
    Isolation and characterization of stable mutants of Streptomyces peucetius defective in daunorubicin biosynthesis
    medical condition treated
    mass
    543.174 dalton
    1 reference
    stated in
    PubChem
    PubChem CID
    31703
    language of work or name
    English
    title
    doxorubicin (English)
    retrieved
    17 November 2016
    Commons category
    Doxorubicin
    0 references

    Identifiers

    HSDB ID
    3070
    1 reference
    stated in
    Hazardous Substances Data Bank
    HSDB ID
    3070
    publication date
    28 October 2019
    title
    DOXORUBICIN (English)
    retrieved
    10 May 2021
    NSC number
    759155
    0 references
    MeSH descriptor ID
    D004317
    subject named as
    Doxorubicin
    0 references
    MeSH concept ID
    M0006784
    0 references
    KEGG ID
    D03899
    1 reference
    stated in
    ChEBI
    ChEBI ID
    28748
    language of work or name
    English
    title
    doxorubicin (English)
    retrieved
    19 October 2016
    PDB ligand ID
    DM2
    0 references
    DeCS ID
    24023
    0 references
    NALT ID
    10464
    0 references
     
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