FR 900523
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| Category | Antibiotics |
| Catalog number | BBF-03566 |
| CAS | 104987-09-9 |
| Molecular Weight | 777.98 |
| Molecular Formula | C42H67NO12 |
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Description
FR 900523, isolated from Streptomyces, suppresses immune response in vitro with IC50 of 1.6 nM for mouse mixed lymphocyte.
Specification
| IUPAC Name | (1R,9S,12S,13R,14S,17R,18E,21S,23S,24R,25S,27R)-1,14-dihydroxy-12-[(E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]prop-1-en-2-yl]-23,25-dimethoxy-13,17,19,21,27-pentamethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone |
| Canonical SMILES | CC1CC(C2C(CC(C(O2)(C(=O)C(=O)N3CCCCC3C(=O)OC(C(C(CC(=O)C(C=C(C1)C)C)O)C)C(=CC4CCC(C(C4)OC)O)C)O)C)OC)OC |
| InChI | InChI=1S/C42H67NO12/c1-23-16-24(2)18-35(52-8)38-36(53-9)20-27(5)42(50,55-38)39(47)40(48)43-15-11-10-12-30(43)41(49)54-37(28(6)33(46)22-32(45)25(3)17-23)26(4)19-29-13-14-31(44)34(21-29)51-7/h17,19,24-25,27-31,33-38,44,46,50H,10-16,18,20-22H2,1-9H3/b23-17+,26-19+/t24-,25+,27+,28+,29-,30-,31+,33-,34+,35-,36-,37+,38+,42+/m0/s1 |
| InChI Key | UBQBKOBGHRTZRG-UPAXIQFWSA-N |
Properties
| Appearance | Colorless Acicular Crystal |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Boiling Point | 861°C at 760 mmHg |
| Melting Point | 152-154°C |
| Density | 1.2 g/cm3 |
Reference Reading
1. FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. I. Taxonomy of the producing strain
H Hatanaka, M Iwami, T Kino, T Goto, M Okuhara J Antibiot (Tokyo). 1988 Nov;41(11):1586-91. doi: 10.7164/antibiotics.41.1586.
A new subspecies of the genus Streptomyces, the proposed name of which is Streptomyces hygroscopicus subsp. yakushimaensis subsp. nov., is described. Soil isolate, strain No. 7238, produces the novel immunosuppressants, FR-900520 and FR-900523. The organism is characterized by its gray aerial mycelium color, hygroscopic spore mass and spiral spore chains with warty or spiny spore surfaces. It is nonchromogenic. Strain No. 7238 shows characteristics most closely related to Streptomyces antimycoticus and S. hygroscopicus, although there are differences in physiological characteristics and carbohydrate utilization. In terms of morphological characteristics, strain No. 7238 is different from S. antimycoticus, but resembles S. hygroscopicus. The differences are not sufficient to establish a new species. It would be most suitable to designate strain No. 7238 as a new subspecies within the species of S. hygroscopicus.
2. FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics
H Hatanaka, T Kino, S Miyata, N Inamura, A Kuroda, T Goto, H Tanaka, M Okuhara J Antibiot (Tokyo). 1988 Nov;41(11):1592-601. doi: 10.7164/antibiotics.41.1592.
FR-900520 and FR-900523, novel neutral macrolide immunosuppressants, were isolated from the cultured broth of Streptomyces hygroscopicus subsp. yakushimaensis No. 7238. Their molecular formulae were determined as C43H69NO12 and C42H67NO12, respectively. The compounds suppressed immune response in vitro. IC50 values of FR-900520 and FR-900523 for mouse mixed lymphocyte reaction were 0.55 nM and 1.6 nM, respectively. FR-900520, the major component, clearly prolonged skin allograft survival in rats.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
