Cinnamycin

CAS 110655-58-8 MFCD01770867

化学结构图

110655-58-8
SMILES: CC(C)[C@@H]1NC(=O)[C@H](Cc2ccccc2)NC(=O)[C@H]2NC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H]3CCCN3C(=O)CNC(=O)[C@H](Cc3ccccc3)NC(=O)[C@@H]3CNCCCC[C@@H](C(=O)O)NC(=O)[C@H]4NC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)[C@H]([C@@H](O)C(=O)O)NC(=O)[C@H](CSC[C@H](NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@@H](N)CS[C@@H]4C)C(=O)N[C@@H](CS[C@H]2C)C(=O)N3)NC1=O

化学属性

Mol. Weight2041.29
Mol. FormulaC89H125N25O25S3

别名和识别编码

Synonym Antibiotic NSC-71936 Ro 09-0198 Ro-09-0198 Lanthiopeptin NSC-71936 Lanthiopeptin NSC-71936 Ro 09-0198
MDL NumberMFCD01770867
CAS Number110655-58-8
InChIKeyQJDWKBINWOWJNZ-IDGBIKHQSA-N
Chemical NameCinnamycin
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分类

  • {SNA} Antibiotics A to Z,
  • {SNA} Antibiotics A to Z, Antibiotics A-F, Antifungal, Bioactive Small Molecule Alphabetical Index, CI-CZ, Chemical Structure Class, Interferes with Cell Membrane Permeability (Ionophores), Lipids in Cell Signaling, Mechanism of Action, Peptides, Phospholipase Inhibitors, Phospholipid Metabolism, Spectrum of Activity, 抗生素, 生化试剂, 生物活性小分子, 细胞信号转导和神经科学, 细胞生物学
  • {SNA} Antibiotics, Antibiotics A to Z, Antibiotics A-F, Antifungal, Bioactive Small Molecules, CI-CY, Cell Biology,

相关文献及参考

  • 1. Fredenhagen, A., et al., Duramycins B and C, two new lanthionine containing antibiotics as inhibitors of phospholipase A2. Structural revision of duramycin and cinnamycin. J. Antibiot. 43 , 1403-1412, (1990)
  • 2. Okesli, A., et al., Nine Post -translational modifications during the biosynthesis of cinnamycin. J. Am. Chem. Soc. 133 , 13753-13760, (2011)
  • 3. Widdick, D. A. et al., Cloning and engineering of the cinnamycin biosynthetic gene cluster from Streptomyces cinnamoneus cinnamoneus DSM 40005 Proc. Natl. Acad. Sci. U. S. A. 100 , 4316-4321, (2003) 摘要
  • 4. Makino, A., et al., Cinnamycin (Ro 09-0198) promotes cell binding and toxicity by inducing transbilayer lipid movement. J. Biol. Chem. 278 , 3204-3209, (2003)
  • 5. Zhao, M., Lantibiotics as probes for phosphatidylethanolamine. Amino Acids 41 , 1071-1079, (2011)
  • 6. Wakamiya, T., et al., Lanthiopeptin, a new peptide effective against herpes simplex virus: Structural determination and comparison with Ro 09-0198, an immunopotentiating peptide. Tetrahedron Lett. 29 , 3771-4772, (1988)
  • Machiadze, G., et al., Specific binding of Ro 09-0198 (cinnamycin) to phosphatidylethanolamine: a thermodynamic analysis. Biochemistry 41 , 1965-1971, (2002)

安全信息

WGK Germany3
RTECSGE1745000
Personal Protective Equipment Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2500 ug/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),249,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Subcutaneous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 400 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),249,1980

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 2 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- ,  Berdy, J., Boca
   Raton, FL, CRC Press, 1980-  Volume(issue)/page/year: 4(1),249,1980

系列性分类


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