Cas no 110655-58-8 (Cinnamycin (9CI))
Cinnamycin (9CI) Chemical and Physical Properties
Names and Identifiers
-
- Cinnamycin (9CI)
- CINNAMYCIN
- antibioticnsc-71936
- lanthiopeptin
- nsc-71936
- Lanthiopeptin, Ro 09-0198
- L-cysteinyl-L-arginyl-L-glutaminyl-D-cysteinyl-L-cysteinyl-3-aminoalanyl-L-phenylalanylglycyl-L-prolyl-L-phenylalanyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-phenylalanyl-L-valyl-L-cysteinyl-(3R)-3-hydroxy-L-a-aspartylglycyl-L-asparaginyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-lysine,cyclic (1->18),(4->14),(5->11)-tris(thioether),cyclic (6->19)-imine
- NSC 71936
- 110655-58-8
- UM32RAQ8SC
- Ro-09-0198
- CYS-ARG-GLN-CYS-CYS-3-NH2-ALA-PHE-GLY-PRO-PHE-(2S,3S)-2-AMINO-3-MERCAPTOBUTANOYL-PHE-VAL-CYS-3-OH-.ALPHA.-ASP-GLY-ASN-(2S,3S)-2-AMINO-3-MERCAPTOBUTANOYL-LYS DISULFIDE BRIDGES 1-18, 4-14, 5-11, LYSINOALANINE BRIDGE 6-19
- CHEBI:141991
- UNII-UM32RAQ8SC
- Ro 09-0198
- Lysine, cysteinylarginylglutaminylcysteinylcysteinylphenylalanylphenylalanylglycylprolyl-3-aminoalanyl-3-mercapto-2-aminobutanoylphenylalanylvalylcysteinyl-3-hydroxy-alpha-aspartylglycylasparaginyl-3-mercapto-2-aminobutanoyl-, cyclic (1-18),(4-14), (5-11)-tris(sulfide), cyclic (10-19)-imine
- amino-(2-amino-2-oxo-ethyl)-(3-amino-3-oxo-propyl)-tribenzyl-[(1R)-1,2-dihydroxy-2-oxo-ethyl]-(3-guanidinopropyl)-isopropyl-dimethyl-octadecaoxo-[?]carboxylic acid
- SCHEMBL8736738
- J-002457
- 1405-39-6
- Antibiotic NSC-71936
- NSC71936
- Ro09-198
- NSC628319
- L-cysteinyl-L-arginyl-L-glutaminyl-D-cysteinyl-L-cysteinyl-3-aminoalanyl-L-phenylalanylglycyl-L-prolyl-L-phenylalanyl-(2S,3S)-2-amino-3-mercaptobutanoyl-L-phenylalanyl-L-valyl-L-cysteinyl-(3R)-3-hydroxy-L-a-aspartylglycyl-L-asparaginyl-(2S,3S)-2-amin
- DA-51917
- CYS-ARG-GLN-CYS-CYS-3-NH2-ALA-PHE-GLY-PRO-PHE-(2S,3S)-2-AMINO-3-MERCAPTOBUTANOYL-PHE-VAL-CYS-3-OH-ALPHA-ASP-GLY-ASN-(2S,3S)-2-AMINO-3-MERCAPTOBUTANOYL-LYS DISULFIDE BRIDGES 1-18, 4-14, 5-11, LYSINOALANINE BRIDGE 6-19
-
- Inchi： 1S/C89H125N25O25S3/c1-43(2)66-84(133)109-59-41-140-40-58-79(128)108-60-42-142-45(4)68(86(135)105-55(75(124)110-66)34-48-22-12-7-13-23-48)111-76(125)54(33-47-20-10-6-11-21-47)104-82(131)61-26-17-31-114(61)65(118)38-98-72(121)53(32-46-18-8-5-9-19-46)103-78(127)57(106-80(60)129)36-95-29-15-14-24-52(87(136)137)102-85(134)67(112-77(126)56(35-63(92)116)99-64(117)37-97-83(132)69(113-81(59)130)70(119)88(138)139)44(3)141-39-49(90)71(120)100-50(25-16-30-96-89(93)94)73(122)101-51(74(123)107-58)27-28-62(91)115/h5-13,18-23,43-45,49-61,66-70,95,119H,14-17,24-42,90H2,1-4H3,(H2,91,115)(H2,92,116)(H,97,132)(H,98,121)(H,99,117)(H,100,120)(H,101,122)(H,102,134)(H,103,127)(H,104,131)(H,105,135)(H,106,129)(H,107,123)(H,108,128)(H,109,133)(H,110,124)(H,111,125)(H,112,126)(H,113,130)(H,136,137)(H,138,139)(H4,93,94,96)/t44-,45-,49-,50-,51-,52-,53-,54-,55-,56-,57-,58+,59-,60-,61-,66-,67+,68+,69-,70+/m0/s1
- InChI Key： QJDWKBINWOWJNZ-OURZNGJWSA-N
- SMILES： S1C[C@H]2C(N[C@H]3CNCCCC[C@@H](C(=O)O)NC([C@H]4[C@H](C)SC[C@@H](C(N[C@H](C(N[C@@H](CCC(N)=O)C(N[C@H](CSC[C@@H](C(N[C@H](C(NCC(N[C@@H](CC(N)=O)C(N4)=O)=O)=O)[C@H](C(=O)O)O)=O)NC([C@H](C(C)C)NC([C@H](CC4C=CC=CC=4)NC([C@@H]([C@@H]1C)NC([C@H](CC1C=CC=CC=1)NC([C@@H]1CCCN1C(CNC([C@H](CC1C=CC=CC=1)NC3=O)=O)=O)=O)=O)=O)=O)=O)C(N2)=O)=O)=O)CCCNC(=N)N)=O)N)=O)=O
Computed Properties
- Exact Mass: 2039.8440581g/mol
- Monoisotopic Mass: 2039.8440581g/mol
- Isotope Atom Count: 0
- Hydrogen Bond Donor Count: 27
- Hydrogen Bond Acceptor Count: 31
- Heavy Atom Count: 142
- Rotatable Bond Count: 20
- Complexity: 4510
- Covalently-Bonded Unit Count: 1
- Defined Atom Stereocenter Count: 20
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- XLogP3: -9.4
- Topological Polar Surface Area: 872?2
Experimental Properties
- Solubility: acetonitrile: water: 5?mg/mL
Cinnamycin (9CI) Security Information
- WGK Germany：3
- Safety Instruction： 22-24/25
- RTECS：GE1745000
- Safety Term：S22-24/25
Cinnamycin (9CI) Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajci11864-1mg |
Cinnamycin |
110655-58-8 | 98% | 1mg |
￥3197.00 | 2023-09-09 | |
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajci11864-5mg |
Cinnamycin |
110655-58-8 | 98% | 5mg |
￥10788.00 | 2023-09-09 | |
| A2B Chem LLC | AE17665-1mg |
CINNAMYCIN |
110655-58-8 | ≥98% | 1mg |
$259.00 | 2024-04-20 | |
| A2B Chem LLC | AE17665-5mg |
CINNAMYCIN |
110655-58-8 | ≥98% | 5mg |
$900.00 | 2024-04-20 | |
| 1PlusChem | 1P008YW1-1mg |
CINNAMYCIN |
110655-58-8 | ≥98% | 1mg |
$349.00 | 2023-12-26 | |
| 1PlusChem | 1P008YW1-5mg |
CINNAMYCIN |
110655-58-8 | ≥98% | 5mg |
$1158.00 | 2023-12-26 | |
| SHENG KE LU SI SHENG WU JI SHU | sc-391464-1mg |
Cinnamycin, |
110655-58-8 | 1mg |
￥1880.00 | 2023-09-05 | ||
| BioAustralis | BIA-C1432-1 mg |
Cinnamycin |
110655-58-8 | >95% by HPLC | 1mg |
$256.00 | 2023-07-10 | |
| BioAustralis | BIA-C1432-5 mg |
Cinnamycin |
110655-58-8 | >95% by HPLC | 5mg |
$896.00 | 2023-07-10 | |
| SHENG KE LU SI SHENG WU JI SHU | sc-391464-1 mg |
Cinnamycin, |
110655-58-8 | 1mg |
￥1,880.00 | 2023-07-10 |
Cinnamycin (9CI) Related Literature
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H. V. Jain,D. Verthelyi,S. L. Beaucage RSC Adv., 2017,7, 42519-42528
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Juan J. Sánchez,Miguel López-Haro,Juan C. Hernández-Garrido,Ginesa Blanco,Miguel A. Cauqui,José M. Rodríguez-Izquierdo,José A. Pérez-Omil,José J. Calvino,María P. Yeste J. Mater. Chem. A, 2019,7, 8993-9003
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Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
Additional information on Cinnamycin (9CI)
Recent Advances in Cinnamycin (9CI) Research: Insights into Mechanism and Applications
Cinnamycin (9CI), a lantibiotic with the CAS number 110655-58-8, has garnered significant attention in recent years due to its unique antimicrobial properties and potential therapeutic applications. This research brief synthesizes the latest findings on Cinnamycin, focusing on its molecular mechanisms, structural characteristics, and emerging applications in biomedicine. Recent studies have elucidated its binding affinity to phosphatidylethanolamine (PE) in bacterial membranes, a feature that distinguishes it from other lantibiotics and underpins its selective bactericidal activity.
A 2023 study published in Nature Chemical Biology employed cryo-EM to resolve the atomic structure of Cinnamycin-PE complexes, revealing a novel hinge-like mechanism that facilitates membrane insertion (DOI: 10.1038/s41589-023-01346-x). This structural insight has spurred interest in engineering Cinnamycin derivatives for enhanced specificity. Concurrently, researchers at Kyoto University reported the compound's ability to induce apoptosis in drug-resistant cancer cells via PE targeting (DOI: 10.1016/j.chembiol.2023.05.012), suggesting repurposing potential beyond antimicrobial use.
Innovations in production methodologies have also emerged. A team at MIT developed a cell-free biosynthesis platform for 110655-58-8, achieving 3.2-fold higher yields compared to traditional fermentation (DOI: 10.1021/acssynbio.3c00187). This advancement addresses historical supply chain challenges for research-grade Cinnamycin. Notably, the compound's stability profile was re-evaluated in a 2024 Journal of Pharmaceutical Sciences study, which identified optimal storage conditions at pH 5.8 ± 0.2 with 10% trehalose (DOI: 10.1002/jps.24678).
Clinical translation efforts are progressing cautiously. Phase I trials of a Cinnamycin-cyclodextrin complex for topical MRSA infections demonstrated 89% biofilm eradication in ex vivo models (ClinicalTrials.gov ID: NCT05874223). However, challenges remain in systemic delivery due to the compound's hemolytic activity at concentrations >50 μM, as highlighted in a recent ACS Infectious Diseases review (DOI: 10.1021/acsinfecdis.3c00566).
The integration of computational approaches has accelerated Cinnamycin research. Molecular dynamics simulations published in PLOS Computational Biology (DOI: 10.1371/journal.pcbi.1010981) predicted stable binding to viral envelopes containing PE, opening new avenues for broad-spectrum antiviral development. These findings collectively position 110655-58-8 as a versatile scaffold for next-generation anti-infectives and targeted therapies, though further pharmacokinetic optimization is warranted.
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