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clavulanic acid (Q415709)

From Wikidata
Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria
  • (2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
  • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
  • Clavulanic Acid
  • Clavulansaeure
  • Acidum clavulanicum
  • Acide clavulanique
  • MM 14151
  • Acido clavulanico
  • Antibiotic mm 14151
  • BRL-14151
  • ácido clavulánico
  • Clavulansäure
  • clavulonic acid
  • Clavulanate
  • acide clavulanique
  • Antibiotic MM 14151
  • Clavulanic acid
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Language Label Description Also known as
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    English
    clavulanic acid
    Β-lactam molecule used as β-lactamase inhibitor to overcome antibiotic resistance in bacteria
    • (2R,3Z,5R)-3-(2-HYDROXYETHYLIDENE)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
    • (Z)-(2R,5R)-3-(2-Hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo(3.2.0)heptane-2-carboxylic acid
    • Clavulanic Acid
    • Clavulansaeure
    • Acidum clavulanicum
    • Acide clavulanique
    • MM 14151
    • Acido clavulanico
    • Antibiotic mm 14151
    • BRL-14151
    • ácido clavulánico
    • Clavulansäure
    • clavulonic acid
    • Clavulanate
    • acide clavulanique
    • Antibiotic MM 14151
    • Clavulanic acid

    Statements

    subclass of
    alkaloid
    0 references
    chemical structure
    Clavulanic acid.svg
    512 × 360; 5 KB
    0 references
    mass
    199.048 dalton
    1 reference
    stated in
    PubChem
    PubChem CID
    5280980
    language of work or name
    English
    title
    CLAVULANIC ACID (English)
    retrieved
    19 October 2016
    chemical formula
    C₈H₉NO₅
    1 reference
    stated in
    PubChem
    PubChem CID
    5280980
    language of work or name
    English
    title
    CLAVULANIC ACID (English)
    retrieved
    19 November 2016
    canonical SMILES
    C1C2N(C1=O)C(C(=CCO)O2)C(=O)O
    1 reference
    stated in
    PubChem
    PubChem CID
    5280980
    language of work or name
    English
    title
    CLAVULANIC ACID (English)
    retrieved
    19 November 2016
    isomeric SMILES
    C1[C@@H]2N(C1=O)[C@H](/C(=C/CO)/O2)C(=O)O
    1 reference
    stated in
    PubChem
    PubChem CID
    5280980
    language of work or name
    English
    title
    CLAVULANIC ACID (English)
    retrieved
    19 November 2016
    found in taxon
    Streptomyces clavuligerus
    69 references
    stated in
    The origin of the β-lactam carbons of clavulanic acid
    stated in
    Evidence that arginine is a later metabolic intermediate than ornithine in the biosynthesis of clavulanic acid by Streptomyces clavuligerus
    stated in
    Evidence that the immediate biosynthetic precursor of clavulanic acid is its N-aldehyde analogue
    stated in
    Biosynthesis of clavulanic acid: origin of the C3 unit
    stated in
    Biosynthesis of clavulanic acid: origin of the C5 unit
    stated in
    The stereochemical fate of (2RS,5R)- and (2RS,5S)-[5-3H]ornithine in clavulanic acid biosynthesis
    stated in
    Clavulanic acid biosynthesis: the stereochemical course of β-lactam formation from chiral glycerol
    stated in
    The role of molecular oxygen in clavulanic acid biosynthesis: evidence for a bacterial oxidative deamination
    stated in
    Cloning, sequencing and disruption of a gene from Streptomyces clavuligerus involved in clavulanic acid biosynthesis
    stated in
    A novel finding that Streptomyces clavuligerus can produce the antibiotic clavulanic acid using olive oil as a sole carbon source.
    stated in
    Induction of Holomycin Production and Complex Metabolic Changes by the argR Mutation in Streptomyces clavuligerus NP1
    stated in
    Data set of in silico simulation for the production of clavulanic acid and cephamycin C by Streptomyces clavuligerus using a genome scale metabolic model
    stated in
    Two sets of paralogous genes encode the enzymes involved in the early stages of clavulanic acid and clavam metabolite biosynthesis in Streptomyces clavuligerus
    stated in
    A putative antimicrobial peptide from Hymenoptera in the megaplasmid pSCL4 of ATCC 27064 reveals a singular case of horizontal gene transfer with potential applications
    stated in
    An improved HPLC-DAD method for clavulanic acid quantification in fermentation broths of Streptomyces clavuligerus
    stated in
    Coordination of glycerol utilization and clavulanic acid biosynthesis to improve clavulanic acid production in Streptomyces clavuligerus
    stated in
    Homologous expression of lysA encoding diaminopimelic acid (DAP) decarboxylase reveals increased antibiotic production in Streptomyces clavuligerus
    stated in
    The claR gene of Streptomyces clavuligerus, encoding a LysR-type regulatory protein controlling clavulanic acid biosynthesis, is linked to the clavulanate-9-aldehyde reductase (car) gene
    stated in
    Mutants of Streptomyces clavuligerus with disruptions in different genes for clavulanic acid biosynthesis produce large amounts of holomycin: possible cross-regulation of two unrelated secondary metabolic pathways
    stated in
    A pathway‐specific transcriptional activator regulates late steps of clavulanic acid biosynthesis in Streptomyces clavuligerus
    stated in
    Clavulanic acid production estimation based on color and structural features of Streptomyces clavuligerus bacteria using self-organizing map and genetic algorithm.
    stated in
    Role of the cmcH–ccaR intergenic region and ccaR overexpression in cephamycin C biosynthesis in Streptomyces clavuligerus
    stated in
    Genome-wide gene expression changes in an industrial clavulanic acid overproduction strain of Streptomyces clavuligerus
    stated in
    Different proteins bind to the butyrolactone receptor protein ARE sequence located upstream of the regulatory ccaR gene of Streptomyces clavuligerus
    stated in
    Proteome-wide alterations in an industrial clavulanic acid producing strain of Streptomyces clavuligerus
    stated in
    Functional analysis of the gene encoding the clavaminate synthase 2 isoenzyme involved in clavulanic acid biosynthesis in Streptomyces clavuligerus
    stated in
    Improvement of clavulanic acid production in Streptomyces clavuligerus by genetic manipulation of structural biosynthesis genes
    stated in
    A statistical approach using L(25) orthogonal array method to study fermentative production of clavulanic acid by Streptomyces clavuligerus MTCC 1142.
    stated in
    Genes specific for the biosynthesis of clavam metabolites antipodal to clavulanic acid are clustered with the gene for clavaminate synthase 1 in Streptomyces clavuligerus
    stated in
    5S clavam biosynthetic genes are located in both the clavam and paralog gene clusters in Streptomyces clavuligerus.
    stated in
    Clavulanic acid production by the MMS 150 mutant obtained from wild type Streptomyces clavuligerus ATCC 27064.
    stated in
    In vivo functional analysis of a class A β-lactamase-related protein essential for clavulanic acid biosynthesis in Streptomyces clavuligerus
    stated in
    Effect of water activity on production of beta-lactam antibiotics by Streptomyces clavuligerus in submerged culture
    stated in
    5S Clavam Biosynthesis Is Controlled by an Atypical Two-Component Regulatory System in Streptomyces clavuligerus
    stated in
    Improved production of clavulanic acid by reverse engineering and overexpression of the regulatory genes in an industrial Streptomyces clavuligerus strain
    stated in
    Characterization of DNA‐binding sequences for CcaR in the cephamycin–clavulanic acid supercluster of Streptomyces clavuligerus
    stated in
    Streptomyces clavuligerus has a second copy of the proclavaminate amidinohydrolase gene
    stated in
    Role of σ-factor (orf21) in clavulanic acid production in Streptomyces clavuligerus NRRL3585
    stated in
    Proteomics analysis of global regulatory cascades involved in clavulanic acid production and morphological development in Streptomyces clavuligerus
    stated in
    Enhanced biosynthesis of clavulanic acid in Streptomyces clavuligerus due to oxidative challenge by redox-cycling agents
    stated in
    High concentrations of clavulanic acid but not of its degradation products decrease glycerol consumption and oxygen uptake rates in cultures of Streptomyces clavuligerus
    stated in
    Characterization of the Metabolic Response of Streptomyces clavuligerus to Shear Stress in Stirred Tanks and Single-Use 2D Rocking Motion Bioreactors for Clavulanic Acid Production
    stated in
    Morphological differentiation and clavulanic acid formation are affected in a Streptomyces clavuligerus adpA-deleted mutant
    stated in
    A comparison of the clavam biosynthetic gene clusters in Streptomyces antibioticus Tü1718 and Streptomyces clavuligerus
    stated in
    Streptomyces clavuligerus shows a strong association between TCA cycle intermediate accumulation and clavulanic acid biosynthesis.
    stated in
    Activation of Secondary Metabolite Gene Clusters in by the PimM Regulator of
    stated in
    Draft genome sequence of Streptomyces clavuligerus NRRL 3585, a producer of diverse secondary metabolites.
    stated in
    Expression of ccaR, encoding the positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus, is dependent on bldG.
    stated in
    Dissociation of cephamycin C and clavulanic acid biosynthesis by 1,3-diaminopropane in Streptomyces clavuligerus
    stated in
    Production of clavulanic acid and cephamycin C by Streptomyces clavuligerus in palm-oil medium
    stated in
    An approach to strain improvement and enhanced production of clavulanic acid in Streptomyces clavuligerus
    stated in
    Improvement for the production of clavulanic acid by mutant Streptomyces clavuligerus
    stated in
    Screening of medium constituents for clavulanic acid production by Streptomyces clavuligerus.
    stated in
    A quantitative approach to characterizing cell lysis caused by mechanical agitation of Streptomyces clavuligerus.
    stated in
    Expansion of the clavulanic acid gene cluster: identification and in vivo functional analysis of three new genes required for biosynthesis of clavulanic acid by Streptomyces clavuligerus
    stated in
    Morphology and clavulanic acid production of Streptomyces clavuligerus: Effect of stirrer speed in batch fermentations
    stated in
    Transcriptional Studies on a Streptomyces clavuligerus oppA2 Deletion Mutant: N-Acetylglycyl-Clavaminic Acid Is an Intermediate of Clavulanic Acid Biosynthesis
    stated in
    Complete Genome Sequence of Streptomyces clavuligerus F613-1, an Industrial Producer of Clavulanic Acid
    stated in
    The CagRS Two-Component System Regulates Clavulanic Acid Metabolism via Multiple Pathways in F613-1
    stated in
    An rplKDelta29-PALG-32 mutation leads to reduced expression of the regulatory genes ccaR and claR and very low transcription of the ceaS2 gene for clavulanic acid biosynthesis in Streptomyces clavuligerus
    stated in
    Shear conditions in clavulanic acid production by Streptomyces clavuligerus in stirred tank and airlift bioreactors.
    stated in
    Clavulanic acid production by Streptomyces clavuligerus: biogenesis, regulation and strain improvement
    stated in
    The positive activator of cephamycin C and clavulanic acid production in Streptomyces clavuligerus is mistranslated in a bldA mutant
    stated in
    Identification of the gene cluster for the dithiolopyrrolone antibiotic holomycin in Streptomyces clavuligerus
    stated in
    Streptomyces clavuligerus relA-null mutants overproduce clavulanic acid and cephamycin C: negative regulation of secondary metabolism by (p)ppGpp
    stated in
    Application of Acid and Cold Stresses to Enhance the Production of Clavulanic Acid by Streptomyces clavuligerus
    stated in
    Clavulanic acid: a beta-lactamase-inhiting beta-lactam from Streptomyces clavuligerus
    stated in
    Five additional genes are involved in clavulanic acid biosynthesis in Streptomyces clavuligerus.
    stated in
    Enzymes catalyzing the early steps of clavulanic acid biosynthesis are encoded by two sets of paralogous genes in Streptomyces clavuligerus
    has part(s)
    carbon
    0 references
    Commons category
    Clavulanic acid
    0 references

    Identifiers

    Reaxys registry number
    787059
    1 reference
    stated in
    ChEBI
    ChEBI ID
    48947
    language of work or name
    English
    title
    clavulanic acid (English)
    retrieved
    19 October 2016
    ChEMBL ID
    CHEMBL777
    1 reference
    stated in
    ChEMBL
    ChEMBL ID
    CHEMBL777
    language of work or name
    English
    title
    CLAVULANIC ACID (English)
    retrieved
    19 November 2016
    ECHA Substance Infocard ID
    100.055.500
    1 reference
    stated in
    ECHA Substance Infocard database
    ECHA Substance Infocard ID
    100.055.500
    retrieved
    27 December 2018
    title
    Clavulanic acid (English)
    quotation
    CAS no.: 58001-44-8 (English)
    KNApSAcK ID
    C00018091
    1 reference
    stated in
    ChEBI
    ChEBI ID
    48947
    language of work or name
    English
    title
    clavulanic acid (English)
    retrieved
    19 October 2016
    KEGG ID
    D07711
    1 reference
    stated in
    ChEBI
    ChEBI ID
    48947
    language of work or name
    English
    title
    clavulanic acid (English)
    retrieved
    19 October 2016
    PDB ligand ID
    J01
    0 references
    CAB ID
    60862
    1 reference
    stated in
    CAB Thesaurus
    retrieved
    6 April 2020
     
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