Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA004480
PROPERTIES
| NPAID | NPA004480 |
|---|---|
| CLUSTER ID | 2321 |
| NODE ID | 1834 |
| NAME | Chlorofusin |
| FORMULA | C63H99ClN12O19 |
| MOLECULAR WEIGHT (Da) | 1364.0030 |
| ACCURATE MASS (Da) | 1362.6838 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Fusarium |
| ORIGIN SPECIES | sp. |
| InChIKey | VQSGYKUTGGRSPK-KXORIUPLSA-N |
| InChI | InChI=1S/C63H99ClN12O19/c1-11-13-14-15-16-17-21-37-54(86)68-38(22-18-24-76-30-36-46(51(83)63(76)23-19-25-94-63)47(64)52(84)62(10,50(36)82)95-45(81)20-12-2)55(87)74-48(34(8)77)60(92)67-33(7)53(85)70-41(28-43(65)79)57(89)72-42(29-44(66)80)58(90)71-40(27-32(5)6)59(91)75-49(35(9)78)61(93)73-39(26-31(3)4)56(88)69-37/h30-35,37-42,48-49,51,77-78,83H,11-29H2,1-10H3,(H2,65,79)(H2,66,80)(H,67,92)(H,68,86)(H,69,88)(H,70,85)(H,71,90)(H,72,89)(H,73,93)(H,74,87)(H,75,91)/t33-,34-,35-,37-,38-,39-,40-,41+,42-,48+,49+,51+,62-,63-/m1/s1 |
| SMILES | CCCCCCCC[C@H]1NC(=O)[C@@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CCCN2C=C3C(=O)[C@@](C)(OC(=O)CCC)C(=O)C(Cl)=C3[C@H](O)[C@]23CCCO3)NC1=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Duncan, Sara J.; Grüschow, Sabine; Williams, Dudley H.; McNicholas, Carole; Purewal, Ravinder; Hajek, Michaela; Gerlitz, Martin; Martin, Steven; Wrigley, Stephen K.; Moore, Michael Isolation and Structure Elucidation of Chlorofusin, a Novel p53-MDM2 Antagonist from aFusariumsp Journal of the American Chemical Society 2001 123 (4) 554-560. | ||
|---|---|---|---|
| DOI | 10.1021/ja002940p | PMID | 11456567 |
SYNTHESES
| CITATION 1 | Clark RC; Lee SY; Boger DL Total synthesis of chlorofusin, its seven chromophore diastereomers, and key partial structures. Journal of the American Chemical Society 2008 130 (37) 12355-12369. DOI: 10.1021/ja8012819 PMID: 18712872 | ||
|---|---|---|---|
| CITATION 2 | Lee SY; Clark RC; Boger DL Total synthesis, stereochemical reassignment, and absolute configuration of chlorofusin. Journal of the American Chemical Society 2007 129 (32) 9860-9861. DOI: 10.1021/ja073264v PMID: 17637057 | ||
| CITATION 3 | Qian WJ; Wei WG; Zhang YX; Yao ZJ Total synthesis, assignment of absolute stereochemistry, and structural revision of chlorofusin. Journal of the American Chemical Society 2007 129 (20) 6400-6401. DOI: 10.1021/ja072225g PMID: 17472388 | ||
| CITATION 4 | Clark RC; Lee SY; Searcey M; Boger DL The isolation, total synthesis and structure elucidation of chlorofusin, a natural product inhibitor of the p53-mDM2 protein-protein interaction. Natural Product Reports 2009 26 (4) 465-477. DOI: 10.1039/b821676b PMID: 19642417 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCCCCCC[C@@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)NC(C(=O)NC(C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N1)CC(C)C)[C@@H](C)O)CC(C)C)CC(=O)N)CC(=O)N)C)[C@@H](C)O)CCCN2C=C3C(=C(C(=O)[C@@](C3=O)(C)OC(=O)CCC)Cl)[C@@H]([C@@]24CCCO4)C | Duncan, Sara J.; Grüschow, Sabine; Williams, Dudley H.; McNicholas, Carole; Purewal, Ravinder; Hajek, Michaela; Gerlitz, Martin; Martin, Steven; Wrigley, Stephen K.; Moore, Michael Isolation and Structure Elucidation of Chlorofusin, a Novel p53-MDM2 Antagonist from aFusariumsp Journal of the American Chemical Society 2001 123 (4) 554-560. DOI: 10.1021/ja002940p PMID: 11456567 | ||
| 2 | CCCCCCCC[C@H]1NC(=O)[C@@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](CCCN2C=C3C(=O)[C@@](C)(OC(=O)CCC)C(=O)C(Cl)=C3[C@H](O)[C@]23CCCO3)NC1=O | Clark RC; Lee SY; Boger DL Total synthesis of chlorofusin, its seven chromophore diastereomers, and key partial structures. Journal of the American Chemical Society 2008 130 (37) 12355-12369. DOI: 10.1021/ja8012819 PMID: 18712872 | ||
