Cyclosporin H
Basic information
- CAS
83602-39-5- Standard SMILES
C/C=C/C[C@@H](C)[C@@H](O)[C@H]1C(=O)N[C@@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@@H](CC(C)C)C(=O)N(C)[C@H](C(C)C)C(=O)N1C- InChIKey
PMATZTZNYRCHOR-JLPRAAIDSA-N- Molecular formula
- C62H111N11O12
- Average molar mass
- 1,202.6 g/mol
- Monoisotopic mass
- 1,201.84136802
Overview
cyclosporin h has been reported in Trichoderma polysporum and Tolypocladium inflatum with data available.
Names & identifiers
- Preferred name
- Cyclosporin H
- IUPAC
- (3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- English name
- Cyclosporin H
- Molecular formula
- C62H111N11O12
- Molecular weight
- 1202.61
Names & synonyms
Cyclosporin H83602-39-5Cyclosporine HCsh cyclosporinFUO6O3NDNHDTXSID801017527Cyclosporin A, 5-(N-methyl-D-valine)-SANDOZ-37-839(3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone(3R,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((E,1R,2R)-1-hydroxy-2-methylhex-4-enyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undeconeRefChem:129982DTXCID301475716
Show more names
CS-1030CS-1741Sandoz 37-839Cyclosporin H, >=95%Cyclosporin impurity HCyclosporine IMpurity-HCyclosporine Impurity 8
Properties
Computed structural properties
- XLogP
- 7.5
- Topological polar surface area
- 279 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 15
- Heavy atoms
- 85
- Formal charge
- 0
- Complexity
- 2,330
Physicochemical properties
- Melting point
- 148 · 148-151°C
- Boiling point
- 1293.8 · 1293.8±65.0 °C(Predicted)
- Density
- 1.016 · 1.016±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Methanol (Slightly, Heated, Sonicated)
- pka
- 13.32 · 13.32±0.70(Predicted)
- form
- powder
- color
- white to beige
- biological source
- Tolypocladium inflatum
- optical activity
- -100 to · [α]/D -100 to -115°, c = 0.5 in methanol
- Sequence
- Cyclo[{Abu}-{Sar}-{N(Me)Leu}-Val-{N(Me)Leu}-Ala-{d-Ala}-{N(Me)Leu}-{N(Me)Leu}-{d-N(Me)Val}-{N(Me)Bmt(E)}]
- InChIKey
- BQQHPBPTWWXRMU-SXHXJWHLSA-N
- FDA UNII
- 6 O3NDNH · FUO6O3NDNH
- UNSPSC Code
- 51111800 · 51111800
- NACRES
- 77 · NA.77
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- hs_code
- 29420000
- Signal word
- Danger
- Symbol(GHS)
- GHS07,GHS08
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard statements
- H302-H350-H360
- Hazard Classifications
- Acute Tox. 4 OralCarc. 1BRepr. 1B
- Precautionary statements
- P202-P264-P270-P280-P301+P312-P308+P313
Chemistry & industry
Applications
DescriptionCyclosporin 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.
UsesAn immunosuppressant that has revolutionized organ transplantation through its use in the prevention of graft rejection. A group of nonpolar cyclic oligopeptides with immunosupppressant activity.
UsesCyclosporin 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.
UsesCyclosporin 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.
Related reactions
1 records
Compound notes
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