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sirolimus (Q32089)

From Wikidata
pharmaceutical drug
  • rapamycin
  • WY-090217
  • AY-22989
  • (-)-rapamycin
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Language Label Description Also known as
default for all languages
No label defined
    English
    sirolimus
    pharmaceutical drug
    • rapamycin
    • WY-090217
    • AY-22989
    • (-)-rapamycin

    Statements

    subclass of
    alkaloid
    0 references
    (32RS)-rapamycin
    0 references
    chemical formula
    C₅₁H₇₉NO₁₃
    1 reference
    stated in
    PubChem
    PubChem CID
    5284616
    language of work or name
    English
    title
    Rapamycin (English)
    retrieved
    21 September 2016
    canonical SMILES
    CC1CCC2CC(C(=CC=CC=CC(CC(C(=O)C(C(C(=CC(C(=O)CC(OC(=O)C3CCCCN3C(=O)C(=O)C1(O2)O)C(C)CC4CCC(C(C4)OC)O)C)C)O)OC)C)C)C)OC
    1 reference
    stated in
    PubChem
    PubChem CID
    5284616
    language of work or name
    English
    title
    Rapamycin (English)
    retrieved
    21 September 2016
    isomeric SMILES
    CO[C@@H]1C[C@H](C[C@@H](C)[C@@H]2CC(=O)[C@H](C)\C=C(C)\[C@@H](O)[C@@H](OC)C(=O)[C@H](C)C[C@H](C)\C=C\C=C\C=C(C)\[C@H](C[C@@H]3CC[C@@H](C)[C@@](O)(O3)C(=O)C(=O)N4CCCC[C@H]4C(=O)O2)OC)CC[C@H]1O
    1 reference
    stated in
    Global Substance Registration System
    UNII
    W36ZG6FT64
    retrieved
    14 February 2018
    found in taxon
    Streptomyces hygroscopicus
    19 references
    stated in
    Incorporation of acetate, propionate, and methionine into rapamycin by Streptomyces hygroscopicus
    stated in
    Rapamycin (AY-22,989), a new antifungal antibiotic. II. Fermentation, isolation and characterization.
    stated in
    Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
    stated in
    Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
    stated in
    Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
    stated in
    A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
    stated in
    Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors
    stated in
    Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
    stated in
    Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
    stated in
    Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
    stated in
    Draft Genome Sequence of Streptomyces iranensis.
    stated in
    Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
    stated in
    Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
    stated in
    Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
    stated in
    An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
    stated in
    The Pipecolate‐Incorporating Enzyme for the Biosynthesis of the Immunosuppressant Rapamycin — Nucleotide Sequence Analysis, Disruption and Heterologous Expression of Rap P from Streptomyces Hygroscopicus
    stated in
    Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
    stated in
    A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
    stated in
    Isolation and Structure of Homotemsirolimuses A, B, and C
    Streptomyces iranensis
    16 references
    stated in
    Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
    stated in
    Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
    stated in
    Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
    stated in
    A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
    stated in
    Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors
    stated in
    Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
    stated in
    Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
    stated in
    Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
    stated in
    Draft Genome Sequence of Streptomyces iranensis.
    stated in
    Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
    stated in
    Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
    stated in
    Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
    stated in
    An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
    stated in
    The Pipecolate‐Incorporating Enzyme for the Biosynthesis of the Immunosuppressant Rapamycin — Nucleotide Sequence Analysis, Disruption and Heterologous Expression of Rap P from Streptomyces Hygroscopicus
    stated in
    Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
    stated in
    A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
    Streptomyces rapamycinicus
    16 references
    stated in
    Secretion of FK506/FK520 and rapamycin by Streptomyces inhibits the growth of competing Saccharomyces cerevisiae and Cryptococcus neoformans
    stated in
    Cytochrome p450 complement (CYPome) of the avermectin-producer Streptomyces avermitilis and comparison to that of Streptomyces coelicolor A3(2).
    stated in
    Organization of the biosynthetic gene cluster for the macrolide concanamycin A in Streptomyces neyagawaensis ATCC 27449.
    stated in
    A combined approach of classical mutagenesis and rational metabolic engineering improves rapamycin biosynthesis and provides insights into methylmalonyl-CoA precursor supply pathway in Streptomyces hygroscopicus ATCC 29253
    stated in
    Waking up Streptomyces secondary metabolism by constitutive expression of activators or genetic disruption of repressors
    stated in
    Effects of dissolved oxygen level on rapamycin production by pellet-form of Streptomyces hygroscopicus
    stated in
    Studies on process optimization methods for rapamycin production using Streptomyces hygroscopicus ATCC 29253.
    stated in
    Production of rapamycin in Streptomyces hygroscopicus from glycerol-based media optimized by systemic methodology
    stated in
    Draft Genome Sequence of Streptomyces iranensis.
    stated in
    Discovery of actinoplanic acid pathway in reveals a genetically conserved synergism with rapamycin
    stated in
    Carbon source nutrition of rapamycin biosynthesis in Streptomyces hygroscopicus
    stated in
    Organisation of the biosynthetic gene cluster for rapamycin in Streptomyces hygroscopicus: analysis of genes flanking the polyketide synthase
    stated in
    An amplifiable and deletable locus of Streptomyces ambofaciens RP181110 contains a very large gene homologous to polyketide synthase genes
    stated in
    The Pipecolate‐Incorporating Enzyme for the Biosynthesis of the Immunosuppressant Rapamycin — Nucleotide Sequence Analysis, Disruption and Heterologous Expression of Rap P from Streptomyces Hygroscopicus
    stated in
    Effect of nitrogen source on biosynthesis of rapamycin by Streptomyces hygroscopicus
    stated in
    A second type-I PKS gene cluster isolated from Streptomyces hygroscopicus ATCC 29253, a rapamycin-producing strain
    significant drug interaction
    legal status (medicine)
    boxed warning
    1 reference
    reference URL
    https://nctr-crs.fda.gov/fdalabel/ui/spl-summaries/criteria/343802
    title
    FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links. (English)
    mass
    913.555142 dalton
    1 reference
    stated in
    PubChem
    PubChem CID
    5284616
    language of work or name
    English
    title
    Rapamycin (English)
    retrieved
    21 September 2016
    has part(s)
    carbon
    0 references
    hydrogen
    0 references
    oxygen
    0 references
    nitrogen
    0 references
    Commons category
    Sirolimus
    0 references

    Identifiers

    HSDB ID
    7284
    1 reference
    stated in
    Hazardous Substances Data Bank
    HSDB ID
    7284
    publication date
    28 October 2019
    title
    SIROLIMUS (English)
    retrieved
    10 May 2021
    NSC number
    226080
    0 references
    758664
    0 references
    EC number
    610-965-5
    1 reference
    stated in
    ECHA Substance Infocard database
    ECHA Substance Infocard ID
    100.107.147
    retrieved
    27 December 2018
    title
    (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0⁴,⁹]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone (English)
    quotation
    CAS no.: 53123-88-9 (English)
    ECHA Substance Infocard ID
    100.107.147
    1 reference
    stated in
    ECHA Substance Infocard database
    ECHA Substance Infocard ID
    100.107.147
    retrieved
    27 December 2018
    title
    (1R,9S,12S,15R,16E,18R,19R,21R,23S,24E,26E,28E,30S,32S,35R)-1,18-dihydroxy-12-[(2R)-1-[(1S,3R,4R)-4-hydroxy-3-methoxycyclohexyl]propan-2-yl]-19,30-dimethoxy-15,17,21,23,29,35-hexamethyl-11,36-dioxa-4-azatricyclo[30.3.1.0⁴,⁹]hexatriaconta-16,24,26,28-tetraene-2,3,10,14,20-pentone (English)
    quotation
    CAS no.: 53123-88-9 (English)
    Nikkaji ID
    J137.896A
    0 references
    ATC code
    S01XA23
    0 references
    KNApSAcK ID
    C00018055
    0 references
    PDB ligand ID
    RAP
    0 references
    DeCS ID
    33809
    0 references
    NE.se ID
    sirolimus
    0 references
    rapamycin
    0 references
    UNSPSC Code
    51201515
    0 references
     
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