Cymbimicin A

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Category Bioactive by-products
Catalog number BBF-01126
CAS 200563-97-9
Molecular Weight 1053.36
Molecular Formula C59H92N4O14

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Description

It is produced by the strain of Micromonospora sp. A92-313709. Cymbimicin A had a strong affinity with cyclosporin-binding protein, and the affinity between Cymbimicin B and cyclosporin-binding protein was about 100 times lower than that of Cymbimicin A.

Specification

IUPAC Name (6E,13E,15E)-16-[(2S,4S,6S)-6-[(3E,5E)-6-[(3S,4S,5S,6R)-4,5-dihydroxy-5,6-dimethyloxan-3-yl]-3-methylhexa-3,5-dienyl]-4,6-dimethoxyoxan-2-yl]-10-ethyl-5,9,11-trihydroxy-3-methoxy-2,6,12-trimethyl-N-[3-methyl-1-[[(3S,4S,5S)-4-methyl-2-oxo-5-phenyloxolan-3-yl]amino]-1-oxobutan-2-yl]hexadeca-6,13,15-trienamide
Canonical SMILES CCC(C(CC=C(C)C(CC(C(C)C(=O)NC(C(C)C)C(=O)NC1C(C(OC1=O)C2=CC=CC=C2)C)OC)O)O)C(C(C)C=CC=CC3CC(CC(O3)(CCC(=CC=CC4COC(C(C4O)(C)O)C)C)OC)OC)O
InChI InChI=1S/C59H92N2O14/c1-14-46(52(64)38(6)22-18-19-26-44-31-45(70-11)33-59(72-13,75-44)30-29-36(4)21-20-25-43-34-73-41(9)58(10,69)54(43)65)47(62)28-27-37(5)48(63)32-49(71-12)39(7)55(66)60-50(35(2)3)56(67)61-51-40(8)53(74-57(51)68)42-23-16-15-17-24-42/h15-27,35,38-41,43-54,62-65,69H,14,28-34H2,1-13H3,(H,60,66)(H,61,67)/b22-18+,25-20+,26-19+,36-21+,37-27+/t38?,39?,40-,41+,43-,44+,45-,46?,47?,48?,49?,50?,51-,52?,53-,54-,58+,59-/m0/s1
InChI Key OTPHGOIPHMPUPP-VERCOKNXSA-N

Properties

Appearance Amorphous Powder
Melting Point 78-83 °C
Solubility Soluble in Methanol

Reference Reading

1. Cymbimicin A and B, two novel cyclophilin-binding structures isolated from actinomycetes
T Fehr, V F Quesniaux, J J Sanglier, L Oberer, L Gschwind, M Ponelle, W Schilling, S Wehrli, A Enz, G Zenke, W Schuler J Antibiot (Tokyo). 1997 Nov;50(11):893-9. doi: 10.7164/antibiotics.50.893.
Two novel metabolites, cymbimicins A and B, were isolated from the culture broth of a strain of Micromonospora sp. by screening for cyclophilin binding metabolites from actinomycete strains. Cymbimicin A binds to cyclophilin A with a high affinity six fold lower than to that of cyclosporin A. The binding affinity of cymbimicin B is about 100 times lower. The taxonomy of the producing strain, fermentation, isolation, physical and biological properties and structure elucidation are described.

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