Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA014131
PROPERTIES
| NPAID | NPA014131 |
|---|---|
| CLUSTER ID | 2121 |
| NODE ID | 1694 |
| NAME | Sanglifehrin A |
| FORMULA | C60H91N5O13 |
| MOLECULAR WEIGHT (Da) | 1090.4100 |
| ACCURATE MASS (Da) | 1089.6613 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. A92-308110 |
| InChIKey | ONJZYZYZIKTIEG-CFBQITSMSA-N |
| InChI | InChI=1S/C60H91N5O13/c1-11-43-30-37(6)60(63-55(43)72)41(10)53(70)40(9)51(78-60)33-49(69)35(4)20-14-12-15-21-36(5)50-26-17-13-16-25-48(68)39(8)54(71)45(28-27-38(7)66)56(73)62-52(34(2)3)57(74)61-47(32-42-22-18-23-44(67)31-42)58(75)65-29-19-24-46(64-65)59(76)77-50/h12-13,15-18,21-23,25,31,34-35,37,39-41,43,45-54,64,67-71H,11,14,19-20,24,26-30,32-33H2,1-10H3,(H,61,74)(H,62,73)(H,63,72)/b15-12+,17-13+,25-16+,36-21+/t35-,37-,39-,40-,41-,43-,45+,46-,47-,48-,49-,50-,51-,52-,53-,54+,60+/m0/s1 |
| SMILES | CC[C@H]1C[C@@H]([C@@]2([C@H]([C@H]([C@H]([C@@H](O2)C[C@@H]([C@@H](C)CC/C=C/C=C(\C)/[C@@H]3C/C=C/C=C/[C@@H]([C@@H]([C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N4CCC[C@H](N4)C(=O)O3)CC5=CC(=CC=C5)O)C(C)C)CCC(=O)C)O)C)O)O)C)O)C)NC1=O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Fehr, Theodor; Kallen, JOeRG; Oberer, Lukas; Sanglier, Jean-Jacques; Schilling, Wolfgang Sanglifehrins A, B, C and D, novel cyclophilin-binding compounds isolated from Streptomyces sp. A92-308110. II. Structure elucidation, stereochemistry and physico-chemical properties Journal of Antibiotics 1999 52 (5) 474-479. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.52.474 | PMID | 10480571 |
SYNTHESES
| CITATION 1 | Nicolaou KC; Xu J; Murphy F; Barluenga S; Baudoin O; Wei Hx; Gray DL; Ohshima T Total Synthesis of Sanglifehrin A. Angewandte Chemie International Edition 1999 38 (16) 2447-2451. DOI: 10.1002/(SICI)1521-3773(19990816)38:16<2447::AID-ANIE2447>3.0.CO;2-O PMID: 10458817 | ||
|---|---|---|---|
| CITATION 2 | Duan M; Paquette LA Enantioselective Total Synthesis of the Cyclophilin-Binding Immunosuppressive Agent Sanglifehrin A This work was financially supported by Eli Lilly and Company and a Robert Mayer Graduate Fellowship (to M.D.). We thank Prof. K. C. Nicolaou for providing authentic spectra of 1. Angewandte Chemie International Edition 2001 40 (19) 3632-3636. DOI: 10.1002/1521-3773(20011001)40:19<3632::aid-anie3632>3.0.co;2-5 PMID: 11592204 | ||
| CITATION 3 | Paquette LA; Duan M; Konetzki I; Kempmann C A convergent three-component total synthesis of the powerful immunosuppressant (-)-sanglifehrin a. Journal of the American Chemical Society 2002 124 (16) 4257-4270. DOI: 10.1021/ja020091v PMID: 11960455 | ||
