Home Other Building Blocks 104987-12-4
104987-12-4,MFCD06198665
Catalog No.:AA00365Y

104987-12-4 | Ascomycin

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10mg
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$50.00   $35.00
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100mg
90%
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$74.00   $52.00
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250mg
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$89.00   $63.00
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1g
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$226.00   $158.00
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5g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00365Y
Chemical Name:
Ascomycin
CAS Number:
104987-12-4
Molecular Formula:
C43H69NO12
Molecular Weight:
792.0075
MDL Number:
MFCD06198665
SMILES:
CC[C@@H]1C=C(C)C[C@H](C)C[C@H](OC)[C@H]2O[C@](O)([C@@H](C[C@@H]2OC)C)C(=O)C(=O)N2C[C@H](C(=O)O[C@@H]([C@@H]([C@H](CC1=O)O)C)/C(=C/[C@@H]1CC[C@H]([C@@H](C1)OC)O)/C)CCC2
Properties
Properties
 
BP:
868℃  
Form:
Solid  
MP:
153-157°C  
Storage:
Inert atmosphere;-20 ℃;  

Computed Properties
 
Complexity:
1430  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
14  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
56  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
6  
XLogP3:
2.5  

Downstream Synthesis Route

[1]Sinclair,PeterJ.;Wong,Frederick;Staruch,MaryJo;Wiederrecht,Greg;Parsons,WilliamH.;Dumont,Francis;Wyvratt,Matthew[BioorganicandMedicinalChemistryLetters,1996,vol.6,#18,p.2193-2196]

[2]CurrentPatentAssignee:THEUNIVERSITYOFQUEENSLAND-WO2021/248189,2021,A1Locationinpatent:Paragraph00106

[1]Ok,HyunO.;Szumiloski,JohnL.;Beattie,ThomasR.;Goulet,MarkT.;Staruch,MaryJo;Dumont,FrancisJ.;Wyvratt,MatthewJ.[BioorganicandMedicinalChemistryLetters,1997,vol.7,#17,p.2199-2204]

[2]Wiedeman,PaulE.;Fesik,StephenW.;Petros,AndrewM.;Nettesheim,DavidG.;Mollison,KarlW.;Lane,BenjaminC.;Or,YatSun;Luly,JayR.[JournalofMedicinalChemistry,1999,vol.42,#21,p.4456-4461]

[3]CurrentPatentAssignee:DUKEUNIVERSITY-WO2015/106283,2015,A1

[1]Acemoglu,Murat;Andres,Hendrik;Moenius,Thomas[Journaloflabelledcompoundsandradiopharmaceuticals,2002,vol.45,#5,p.361-370]

[2]Hersperger,Rene;Schuler,Walter;Zenke,Gerhard[BioorganicandMedicinalChemistryLetters,1999,vol.9,#2,p.227-232]

[3]Baumann,Karl;Bacher,Markus;Damont,Annelaure;Högenauer,Klemens;Steck,Andrea[Tetrahedron,2003,vol.59,#50,p.10075-10087]

[1]Baumann,Karl;Knapp;Strnadt;Schulz;Grassberger[TetrahedronLetters,1999,vol.40,#44,p.7761-7764]

104987-12-4   
CASUnavailable 

[1]Wiedeman,PaulE.;Fesik,StephenW.;Petros,AndrewM.;Nettesheim,DavidG.;Mollison,KarlW.;Lane,BenjaminC.;Or,YatSun;Luly,JayR.[JournalofMedicinalChemistry,1999,vol.42,#21,p.4456-4461]

Literature

Title: Evaluation, synthesis and characterization of tacrolimus impurities.

Journal: The Journal of antibiotics 20120701

Title: Quantitative analysis of the antifungal drug anidulafungin by LC-online SPE-MS/MS in human plasma.

Journal: Biomedical chromatography : BMC 20120601

Title: An adaptable luminescence resonance energy transfer assay for measuring and screening protein-protein interactions and their inhibition.

Journal: Chembiochem : a European journal of chemical biology 20120305

Title: Identification and elimination of ion suppression in the quantitative analysis of sirolimus in human blood by LC/ESI-MS/MS.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20110415

Title: Opposing action of casein kinase 1 and calcineurin in nucleo-cytoplasmic shuttling of mammalian translation initiation factor eIF6.

Journal: The Journal of biological chemistry 20110128

Title: Chemistry of the immunomodulatory macrolide ascomycin and related analogues.

Journal: Progress in the chemistry of organic natural products 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Study of the effect of Wuzhi tablet (Schisandra sphenanthera extract) on tacrolimus tissue distribution in rat by liquid chromatography tandem mass spectrometry method.

Journal: Biomedical chromatography : BMC 20100401

Title: A method to explore protein side chain conformational variability using experimental data.

Journal: Chemphyschem : a European journal of chemical physics and physical chemistry 20091221

Title: Calcineurin activation by slow calcium release from intracellular stores suppresses protein kinase C regulation of L-type calcium channels in L6 cells.

Journal: Cell calcium 20091001

Title: Screening of small molecule interactor library by using in-cell NMR spectroscopy (SMILI-NMR).

Journal: Journal of medicinal chemistry 20090611

Title: Liquid chromatographic method for the determination of sirolimus in blood using electrochemical detection.

Journal: Biomedical chromatography : BMC 20090301

Title: Procedure for chromatography involving sample solvent with higher elution strength than the mobile phase.

Journal: Journal of chromatography. A 20080111

Title: Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants.

Journal: CNS neuroscience & therapeutics 20080101

Title: Therapeutic drug monitoring of tacrolimus with the dried blood spot method.

Journal: Journal of pharmaceutical and biomedical analysis 20070727

Title: The immunosuppressant cyclosporin A antagonizes human formyl peptide receptor through inhibition of cognate ligand binding.

Journal: Journal of immunology (Baltimore, Md. : 1950) 20061115

Title: Calcineurin inhibitors reduce nuclear localization of transcription factor NFAT in UV-irradiated keratinocytes and reduce DNA repair.

Journal: Journal of molecular histology 20060901

Title: Sensitive, high throughput HPLC-MS/MS method with on-line sample clean-up for everolimus measurement.

Journal: Therapeutic drug monitoring 20060801

Title: Anticonvulsant effect of the calcineurin inhibitor ascomycin on seizures induced by picrotoxin microperfusion in the rat hippocampus.

Journal: Pharmacology, biochemistry, and behavior 20060701

Title: Organic solvents compromise performance of internal standard (ascomycin) in proficiency testing of mass spectrometry-based assays for tacrolimus.

Journal: Clinical chemistry 20060401

Title: Surface-activated chemical ionization and high-flow gradient chromatography to reduce matrix effect.

Journal: Rapid communications in mass spectrometry : RCM 20060101

Title: Calcineurin inhibitors decrease DNA repair and apoptosis in human keratinocytes following ultraviolet B irradiation.

Journal: The Journal of investigative dermatology 20051101

Title: Structure elucidation of new ascomycins produced by genetic engineering.

Journal: The Journal of antibiotics 20051101

Title: The FK506-binding protein of the malaria parasite, Plasmodium falciparum, is a FK506-sensitive chaperone with FK506-independent calcineurin-inhibitory activity.

Journal: Molecular and biochemical parasitology 20050601

Title: Effects of calcineurin inhibitors on an in vitro assay for chronic urticaria.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20050501

Title: Elucidating the substrate specificity and condensation domain activity of FkbP, the FK520 pipecolate-incorporating enzyme.

Journal: Biochemistry 20050426

Title: Antimalarial effects of macrolactones related to FK520 (ascomycin) are independent of the immunosuppressive properties of the compounds.

Journal: The Journal of infectious diseases 20050415

Title: Activation of the phosphoinositide 3-kinase-Akt-mammalian target of rapamycin signaling pathway is required for metabotropic glutamate receptor-dependent long-term depression.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20040714

Title: Substitution of threonine-1351 in the multidrug transporter Cdr1p of Candida albicans results in hypersusceptibility to antifungal agents and threonine-1351 is essential for synergic effects of calcineurin inhibitor FK520.

Journal: The Journal of antimicrobial chemotherapy 20040701

Title: Molecular imaging of drug-modulated protein-protein interactions in living subjects.

Journal: Cancer research 20040315

Title: [Acute promyelocytic leukemia after living donor partial orthotopic liver transplantation].

Journal: [Rinsho ketsueki] The Japanese journal of clinical hematology 20040301

Title: Characterization of programmed cell death 4 in multiple human cancers reveals a novel enhancer of drug sensitivity.

Journal: Molecular cancer therapeutics 20040201

Title: Crystal structure of an Acyl-ACP dehydrogenase from the FK520 polyketide biosynthetic pathway: insights into extender unit biosynthesis.

Journal: Journal of molecular biology 20031128

Title: Ubiquitination regulates PSD-95 degradation and AMPA receptor surface expression.

Journal: Neuron 20031030

Title: Calcineurin directs the reciprocal regulation of calcium entry pathways in nonexcitable cells.

Journal: The Journal of biological chemistry 20031010

Title: Conditional protein splicing: a new tool to control protein structure and function in vitro and in vivo.

Journal: Journal of the American Chemical Society 20030903

Title: Calcineurin antagonists differentially affect mediator secretion, p38 mitogen-activated protein kinase and extracellular signal-regulated kinases from immunologically activated human basophils.

Journal: Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology 20030301

Title: Combination of caspofungin with inhibitors of the calcineurin pathway attenuates growth in vitro in Aspergillus species.

Journal: The Journal of antimicrobial chemotherapy 20030201

Title: In vitro hypoxia and excitotoxicity in human brain induce calcineurin-Bcl-2 interactions.

Journal: Neuroscience 20030101

Title: Cyclosporin A blocks muscle differentiation by inducing oxidative stress and inhibiting the peptidyl-prolyl-cis-trans isomerase activity of cyclophilin A: cyclophilin A protects myoblasts from cyclosporin A-induced cytotoxicity.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20021001

Title: Calcineurin inhibitors and sirolimus: mechanisms of action and applications in dermatology.

Journal: Clinical and experimental dermatology 20021001

Title: Genetically engineered analogs of ascomycin for nerve regeneration.

Journal: The Journal of pharmacology and experimental therapeutics 20020901

Title: The inhibition of the sarcoplasmic/endoplasmic reticulum Ca2+-ATPase by macrocyclic lactones and cyclosporin A.

Journal: The Biochemical journal 20020815

Title: Immunophilins and HIV-1 infection.

Journal: Archives of virology 20020801

Title: A new substrate specificity for acyl transferase domains of the ascomycin polyketide synthase in Streptomyces hygroscopicus.

Journal: The Journal of biological chemistry 20020315

Title: Identification of genes coding enzymes for ascomycin tetra-hydropyranose ring formation.

Journal: International journal of molecular medicine 20020201

Title: Production of a novel FK520 analog in Streptomyces hygroscopicus: improving titer while minimizing impurities.

Journal: Journal of industrial microbiology & biotechnology 20020101

Title: High enzymatic activity and chaperone function are mechanistically related features of the dimeric E. coli peptidyl-prolyl-isomerase FkpA.

Journal: Journal of molecular biology 20010706

Title: Induction of differentiation of human myeloid leukemia cells by immunosuppressant macrolides (rapamycin and FK506) and calcium/calmodulin-dependent kinase inhibitors.

Journal: Experimental hematology 20010501

Title: Ascomycin: an advance in the management of atopic dermatitis.

Journal: The British journal of dermatology 20010401

Title: Signalling pathways regulating the dephosphorylation of Ser729 in the hydrophobic domain of protein kinase Cepsilon upon cell passage.

Journal: The Journal of biological chemistry 20010330

Title: Design of a Gag pentapeptide analogue that binds human cyclophilin A more efficiently than the entire capsid protein: new insights for the development of novel anti-HIV-1 drugs.

Journal: Journal of medicinal chemistry 20000504

Title: Potent immunosuppressive C32-O-arylethyl ether derivatives of ascomycin with reduced toxicity.

Journal: Bioorganic & medicinal chemistry letters 19990719

Title: Ascomycin macrolactam derivative SDZ ASM 981 inhibits the release of granule-associated mediators and of newly synthesized cytokines in RBL 2H3 mast cells in an immunophilin-dependent manner.

Journal: Archives of dermatological research 19980901

Title: Nephrotoxicity studies of the immunosuppressants tacrolimus (FK506) and ascomycin in rat models.

Journal: Toxicology 19980206

Title: Tau phosphorylation in brain slices: pharmacological evidence for convergent effects of protein phosphatases on tau and mitogen-activated protein kinase.

Journal: Molecular pharmacology 19950401

Title: Rapamycin-FKBP inhibits cell cycle regulators of proliferation in vascular smooth muscle cells.

Journal: Circulation research 19950301

Title: Rapamycin-FKBP12 blocks proliferation, induces differentiation, and inhibits cdc2 kinase activity in a myogenic cell line.

Journal: The Journal of biological chemistry 19931205

Title: Hatanaka H, et al. FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics. J Antibiot (Tokyo). 1988 Nov;41(11):1592-601.

Title: Krishika Sambyal, et al. Bioprocess and genetic engineering aspects of ascomycin production: a review. J Genet Eng Biotechnol. 2020 Nov 19;18(1):73.

Title: Germán Sierra-Paredes, et al. Ascomycin and FK506: pharmacology and therapeutic potential as anticonvulsants and neuroprotectants. CNS Neurosci Ther. Spring 2008;14(1):36-46.

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Tags:104987-12-4 Molecular Formula|104987-12-4 MDL|104987-12-4 SMILES|104987-12-4 Ascomycin