Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA013582
PROPERTIES
| NPAID | NPA013582 |
|---|---|
| CLUSTER ID | 4953 |
| NODE ID | 3557 |
| NAME | FR901483 |
| FORMULA | C20H31N2O6P |
| MOLECULAR WEIGHT (Da) | 426.4500 |
| ACCURATE MASS (Da) | 426.1920 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Cladobotryum |
| ORIGIN SPECIES | sp. |
| InChIKey | CIISYBZFZSWZLX-KKMIJOEASA-N |
| InChI | InChI=1S/C20H31N2O6P/c1-21-14-10-20-8-7-18(28-29(24,25)26)16(11-20)19(23)17(22(20)12-14)9-13-3-5-15(27-2)6-4-13/h3-6,14,16-19,21,23H,7-12H2,1-2H3,(H2,24,25,26)/t14-,16-,17-,18-,19-,20+/m0/s1 |
| SMILES | CN[C@@H]1CN2[C@@H](CC3=CC=C(OC)C=C3)[C@@H](O)[C@H]3C[C@@]2(CC[C@@H]3OP(=O)(O)O)C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sakamoto, K; Tsujii, E; Abe, F; Nakanishi, T; Yamashita, M; Shigematsu, N; Izumi, S; Okuhara, M FR901483, a novel immunosuppressant isolated from Cladobotryum sp. No. 11231. Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities Journal of Antibiotics 1996 49 (1) 37. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.49.37 | PMID | 8609083 |
SYNTHESES
| CITATION 1 | Ousmer M; Braun NA; Ciufolini MA Total synthesis of FR901483. Organic Letters 2001 3 (5) 765-7. DOI: 10.1021/ol015526i PMID: 11259057 | ||
|---|---|---|---|
| CITATION 2 | Maeng JH; Funk RL Total synthesis of the immunosuppressant FR901483 via an amidoacrolein cycloaddition. Organic Letters 2001 3 (8) 1125-8. DOI: 10.1021/ol015506g PMID: 11348175 | ||
| CITATION 3 | Kan T; Fujimoto T; Ieda S; Asoh Y; Kitaoka H; Fukuyama T Stereocontrolled total synthesis of potent immunosuppressant FR901483. Organic Letters 2004 6 (16) 2729-31. DOI: 10.1021/ol049074w PMID: 15281755 | ||
| CITATION 4 | Brummond KM; Hong SP A formal total synthesis of (-)-FR901483, using a tandem cationic aza-Cope rearrangement/Mannich cyclization approach. Journal of Organic Chemistry 2005 70 (3) 907-16. DOI: 10.1021/jo0483567 PMID: 15675848 | ||
| CITATION 5 | Carson CA; Kerr MA Total synthesis of FR901483. Organic Letters 2009 11 (3) 777-9. DOI: 10.1021/ol802870c PMID: 19138120 | ||
| CITATION 6 | Ma AJ; Tu YQ; Peng JB; Dou QY; Hou SH; Zhang FM; Wang SH Total synthesis of (-)-FR901483. Organic Letters 2012 14 (14) 3604-7. DOI: 10.1021/ol301331t PMID: 22734865 | ||
| CITATION 7 | Huo HH; Zhang HK; Xia XE; Huang PQ A formal enantioselective total synthesis of FR901483. Organic Letters 2012 14 (18) 4834-7. DOI: 10.1021/ol302165d PMID: 22937903 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CNC1CC23CCC(C(C2)C(C(N3C1)CC4=CC=C(C=C4)OC)O)OP(=O)(O)O | Sakamoto, K; Tsujii, E; Abe, F; Nakanishi, T; Yamashita, M; Shigematsu, N; Izumi, S; Okuhara, M FR901483, a novel immunosuppressant isolated from Cladobotryum sp. No. 11231. Taxonomy of the producing organism, fermentation, isolation, physico-chemical properties and biological activities Journal of Antibiotics 1996 49 (1) 37. DOI: 10.7164/antibiotics.49.37 PMID: 8609083 | ||
| 2 | CN[C@@H]1CN2[C@@H](CC3=CC=C(OC)C=C3)[C@@H](O)[C@H]3C[C@@]2(CC[C@@H]3OP(=O)(O)O)C1 | Snider, Barry B.; Lin, Hong Total Synthesis of (−)-FR901483. Journal of the American Chemical Society 1999 121 (34) 7778-7786. DOI: 10.1021/ja991160h | ||
