Cyclosporin H

Base Information

• Chemical Name: Cyclosporin H
• CAS No.: 83602-39-5
• Molecular Formula: C₆₂H₁₁₁N₁₁O₁₂
• Molecular Weight: 1202.63
• Hs Code.: 29420000
• UNII: FUO6O3NDNH
• DSSTox Substance ID: DTXSID801017527
• Nikkaji Number: J467.031K
• Wikidata: Q27278214
• ChEMBL ID: CHEMBL4448165
• Mol file: 83602-39-5.mol

Synonyms:5-(N-methyl-D-valine)cyclosporine A;CsH cyclosporin;cyclosporin H;cyclosporine H

Chemical Property of Cyclosporin H

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 148-151 °C
• Refractive Index: 1.468
• Boiling Point: 1293.8 °C at 760 mmHg
• PKA: 13.32±0.70(Predicted)
• Flash Point: 736.3 °C
• PSA: 270.01000
• Density: 1.016 g/cm³
• LogP: 4.10080
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 15
• Exact Mass: 1201.84136802
• Heavy Atom Count: 85
• Complexity: 2330

Purity/Quality:

99% ^*data from raw suppliers

Cyclosporin H ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
• Isomeric SMILES: CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C
• Description: Cyclosporin H is a natural cyclic undecapeptide that selectively antagonizes the formyl peptide receptor at concentrations ranging from 0.1 to 10 μM. Unlike cyclosporin A , cyclosporin H does not bind cyclophilin to evoke an immunosuppressant response. Cyclosporin H has been reported to inhibit phorbol ester-mediated effects in mouse skin and block calcium/calmodulin-dependent EF-2 phosphorylation in vitro.
• Uses: Cyclosporin H is a minor analogue of the cyclosporin family which is immunologically inactive as it does not bind to immunophilin. Cyclopsorin H is the most extensively investigated of the minor cyclosporin analogues and displays a range of activities. It is a potent inhibitor of tumour-promoting phorbol esters on mouse skin in vivo, and of calcium/calmodulin-dependent EF-2 phosphorylation in vitro, a potent and selective antagonist of formyl peptide receptor and inhibitor of formyl peptide-induced superoxide formation. Cyclosporin is an immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection.A group of nonpolar cyclic oligopeptides with immunosupppressant activity.

Technology Process of Cyclosporin H

There total 4 articles about Cyclosporin H which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

cyclosporine A (59865-13-3,83602-39-5,122090-69-1,126374-36-5) → C62H111N11O12 (59865-13-3,83602-39-5,122090-69-1,126374-36-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / DMAP / pyridine / 24 °C

2: 90 percent / sodium metaperiodate / OsO₄ / H₂O; dioxane

3: tetrahydrofuran / 2 h / 0 °C

4: CO₃^(2-) / methanol

With dmap; sodium periodate; carbonate^(2-); osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; water;

DOI:10.1016/S0040-4039(01)80693-6

Reference yield:

C64H113N11O13 (83563-94-4,83602-41-9,121652-55-9) → C62H111N11O12 (59865-13-3,83602-39-5,122090-69-1,126374-36-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / sodium metaperiodate / OsO₄ / H₂O; dioxane

2: tetrahydrofuran / 2 h / 0 °C

3: CO₃^(2-) / methanol

With sodium periodate; carbonate^(2-); osmium(VIII) oxide; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1016/S0040-4039(01)80693-6

Reference yield:

C64H113N11O13 (83563-94-4,83602-41-9,121652-55-9) → C62H111N11O12 (59865-13-3,83602-39-5,122090-69-1,126374-36-5)

Guidance literature:

With carbonate^(2-); In methanol; Yield given;

DOI:10.1016/S0040-4039(01)80693-6

upstream raw materials:

C₆₄H₁₁₃N₁₁O₁₃

C₆₂H₁₀₉N₁₁O₁₄

cyclosporine A

C₆₄H₁₁₃N₁₁O₁₃

Downstream raw materials:

C₆₂H₁₁₃N₁₁O₁₂

C₆₉H₁₁₅N₁₁O₁₃

C₆₂H₁₀₉N₁₁O₁₄

C₆₂H₁₁₁N₁₁O₁₂

Refernces