Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA020747
PROPERTIES
| NPAID | NPA020747 |
|---|---|
| CLUSTER ID | 535 |
| NODE ID | 477 |
| NAME | Complestatin |
| FORMULA | C61H45Cl6N7O15 |
| MOLECULAR WEIGHT (Da) | 1328.7830 |
| ACCURATE MASS (Da) | 1325.1105 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | lavendulae SANK 60477 |
| InChIKey | JJGZGELTZPACID-REUTWCLQSA-N |
| InChI | InChI=1S/C61H45Cl6N7O15/c1-74-44(56(82)73-49(61(87)88)25-4-7-32(75)8-5-25)12-24-2-9-33(10-3-24)89-45-22-27-13-35(51(45)77)26-6-11-34-31(23-68-42(34)20-26)21-43(69-59(85)50(76)30-18-40(66)54(80)41(67)19-30)55(81)70-47(28-14-36(62)52(78)37(63)15-28)57(83)71-46(27)58(84)72-48(60(74)86)29-16-38(64)53(79)39(65)17-29/h2-11,13-20,22-23,43-44,46-49,68,75,77-80H,12,21H2,1H3,(H,69,85)(H,70,81)(H,71,83)(H,72,84)(H,73,82)(H,87,88)/t43-,44+,46-,47+,48-,49-/m1/s1 |
| SMILES | CN1C(=O)[C@@H](C2=CC(Cl)=C(O)C(Cl)=C2)NC(=O)[C@@H]2NC(=O)[C@H](C3=CC(Cl)=C(O)C(Cl)=C3)NC(=O)[C@H](NC(=O)C(=O)C3=CC(Cl)=C(O)C(Cl)=C3)CC3=CNC4=C3C=CC(=C4)C3=CC2=CC(=C3O)OC2=CC=C(C=C2)C[C@H]1C(=O)N[C@@H](C(=O)O)C1=CC=C(O)C=C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Kaneko I; Kamoshida K; Takahashi S Complestatin, a potent anti-complement substance produced by Streptomyces lavendulae. I. Fermentation, isolation and biological characterization. Journal of Antibiotics 1989 42 (2) 236-241. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.42.236 | PMID | 2925515 |
SYNTHESES
| CITATION 1 | Garfunkle J; Kimball FS; Trzupek JD; Takizawa S; Shimamura H; Tomishima M; Boger DL Total synthesis of chloropeptin II (complestatin) and chloropeptin I. Journal of the American Chemical Society 2009 131 (44) 16036-16038. DOI: 10.1021/ja907193b PMID: 19839632 | ||
|---|---|---|---|
| CITATION 2 | Wang Z; Bois-Choussy M; Jia Y; Zhu J Total synthesis of complestatin (chloropeptin II). Angewandte Chemie International Edition 2010 49 (11) 2018-22. DOI: 10.1002/anie.200906797 PMID: 20148426 | ||
| CITATION 3 | Shimamura H; Breazzano SP; Garfunkle J; Kimball FS; Trzupek JD; Boger DL Total synthesis of complestatin: development of a Pd(0)-mediated indole annulation for macrocyclization. Journal of the American Chemical Society 2010 132 (22) 7776-83. DOI: 10.1021/ja102304p PMID: 20469945 | ||
| CITATION 4 | Breazzano SP; Boger DL Synthesis and stereochemical determination of complestatin A and B (neuroprotectin A and B). Journal of the American Chemical Society 2011 133 (45) 18495-502. DOI: 10.1021/ja208570q PMID: 21991993 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CN1[C@@H](CC2=CC=C(C=C2)OC3=C(C4=CC(=C3)[C@H](C(=O)N[C@@H](C1=O)C5=CC(=C(C(=C5)Cl)O)Cl)NC(=O)[C@@H](NC(=O)[C@@H](CC6=CNC7=C6C=CC4=C7)NC(=O)C(=O)C8=CC(=C(C(=C8)Cl)O)Cl)C9=CC(=C(C(=C9)Cl)O)Cl)O)C(=O)NC(C1=CC=C(C=C1)O)C(=O)O | Kaneko I; Kamoshida K; Takahashi S Complestatin, a potent anti-complement substance produced by Streptomyces lavendulae. I. Fermentation, isolation and biological characterization. Journal of Antibiotics 1989 42 (2) 236-241. DOI: 10.7164/antibiotics.42.236 PMID: 2925515 | ||
| 2 | CN1C(=O)[C@@H](C2=CC(Cl)=C(O)C(Cl)=C2)NC(=O)[C@@H]2NC(=O)[C@H](C3=CC(Cl)=C(O)C(Cl)=C3)NC(=O)[C@H](NC(=O)C(=O)C3=CC(Cl)=C(O)C(Cl)=C3)CC3=CNC4=C3C=CC(=C4)C3=CC2=CC(=C3O)OC2=CC=C(C=C2)C[C@H]1C(=O)N[C@@H](C(=O)O)C1=CC=C(O)C=C1 | Shimamura H; Breazzano SP; Garfunkle J; Kimball FS; Trzupek JD; Boger DL Total synthesis of complestatin: development of a Pd(0)-mediated indole annulation for macrocyclization. Journal of the American Chemical Society 2010 132 (22) 7776-83. DOI: 10.1021/ja102304p PMID: 20469945 | ||
