Home Other Building Blocks Cyclosporin H

Cyclosporin H

CAS No.:
83602-39-5
Catalog Number:
AG00G294
Molecular Formula:
C62H111N11O12
Molecular Weight:
1202.6112
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$166
- +
5mg
≥95%
1 week
United States
$496
- +
Product Description
Catalog Number:
AG00G294
Chemical Name:
Cyclosporin H
CAS Number:
83602-39-5
Molecular Formula:
C62H111N11O12
Molecular Weight:
1202.6112
MDL Number:
MFCD04039488
IUPAC Name:
(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
InChI:
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50-,51+,52-/m1/s1
InChI Key:
PMATZTZNYRCHOR-JLPRAAIDSA-N
SMILES:
C/C=C/C[C@@H]([C@@H](C1C(=O)NCCCC(=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](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)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)O)C C62H111N11O12
UNII:
FUO6O3NDNH
Properties
Complexity:
2330  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
12  
Defined Bond Stereocenter Count:
1  
Exact Mass:
1201.841g/mol
Formal Charge:
0
Heavy Atom Count:
85  
Hydrogen Bond Acceptor Count:
12  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
1202.635g/mol
Monoisotopic Mass:
1201.841g/mol
Rotatable Bond Count:
15  
Topological Polar Surface Area:
279A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.5  
Literature
Title Journal
Suppression of feline coronavirus replication in vitro by cyclosporin A. Veterinary research 20120101
N-formyl-methionyl-leucyl-phenylalanine (fMLP) promotes osteoblast differentiation via the N-formyl peptide receptor 1-mediated signaling pathway in human mesenchymal stem cells from bone marrow. The Journal of biological chemistry 20110513
Unambiguous assignment of vibrational spectra of cyclosporins A and H. The journal of physical chemistry. A 20100916
Mitochondrial damage associated molecular patterns from femoral reamings activate neutrophils through formyl peptide receptors and P44/42 MAP kinase. Journal of orthopaedic trauma 20100901
Mycobacteria attenuate nociceptive responses by formyl peptide receptor triggered opioid peptide release from neutrophils. PLoS pathogens 20090401
f-Met-Leu-Phe stimulates nitric oxide production in chick embryo neurons: the role of NF-kB. Immunopharmacology and immunotoxicology 20090101
Cyclosporin H, Boc-MLF and Boc-FLFLF are antagonists that preferentially inhibit activity triggered through the formyl peptide receptor. Inflammation 20071201
The immunosuppressant cyclosporin A antagonizes human formyl peptide receptor through inhibition of cognate ligand binding. Journal of immunology (Baltimore, Md. : 1950) 20061115
Cyclosporin A stimulates apical Na+/H+ exchange in LLC-PK1/PKE20 proximal tubular cells. Pediatric nephrology (Berlin, Germany) 20060701
The peptide Trp-Lys-Tyr-Met-Val-D-Met activates neutrophils through the formyl peptide receptor only when signaling through the formylpeptide receptor like 1 is blocked. A receptor switch with implications for signal transduction studies with inhibitors and receptor antagonists. Biochemical pharmacology 20060514
Differential control of glucocorticoid receptor hormone-binding function by tetratricopeptide repeat (TPR) proteins and the immunosuppressive ligand FK506. Biochemistry 20050215
Cyclosporine A and FK506 induce osteoclast apoptosis in mouse bone marrow cell cultures. Bone 20040701
Cytochalasin B triggers a novel pertussis toxin sensitive pathway in TNF-alpha primed neutrophils. BMC cell biology 20040101
Cyclosporine A amplifies Ca2+ signaling pathway in LLC-PK1 cells through the inhibition of plasma membrane Ca2+ pump. Journal of the American Society of Nephrology : JASN 20030601
Two new cyclosporin folds observed in the structures of the immunosuppressant cyclosporin G and the formyl peptide receptor antagonist cyclosporin H at ultra-high resolution. Organic & biomolecular chemistry 20030507
Immunoglobulin superantigen protein L induces IL-4 and IL-13 secretion from human Fc epsilon RI+ cells through interaction with the kappa light chains of IgE. Journal of immunology (Baltimore, Md. : 1950) 20030215
HIV-1 envelope gp41 peptides promote migration of human Fc epsilon RI+ cells and inhibit IL-13 synthesis through interaction with formyl peptide receptors. Journal of immunology (Baltimore, Md. : 1950) 20021015
The synthetic chemoattractant Trp-Lys-Tyr-Met-Val-DMet activates neutrophils preferentially through the lipoxin A(4) receptor. Blood 20000301
Inhibition of vaccinia virus replication by cyclosporin A analogues correlates with their affinity for cellular cyclophilins. The Journal of general virology 19980201
Properties