Compounds
| ID | Spectrum Quality | Annotated Name |
|---|---|---|
| CCMSLIB00000478598 | Bronze | Apratoxin&A |
| CCMSLIB00000478599 | Bronze | Apratoxin&A |
| CCMSLIB00000424840 | Bronze | Apratoxin&A |
| CCMSLIB00000001601 | Gold | 1!CCMSLIB00000001603 |
COMPOUND NPA012281
PROPERTIES
| NPAID | NPA012281 |
|---|---|
| CLUSTER ID | 694 |
| NODE ID | 612 |
| NAME | Apratoxin A |
| FORMULA | C45H69N5O8S |
| MOLECULAR WEIGHT (Da) | 840.1410 |
| ACCURATE MASS (Da) | 839.4867 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Lyngbya |
| ORIGIN SPECIES | majuscula |
| InChIKey | KXUJXPZXILTXDA-JHMIWIOGSA-N |
| InChI | InChI=1S/C45H69N5O8S/c1-13-27(3)38-43(55)50-20-14-15-35(50)44(56)58-37(45(7,8)9)22-26(2)21-36(51)29(5)40-46-32(25-59-40)23-28(4)39(52)47-34(24-31-16-18-33(57-12)19-17-31)42(54)48(10)30(6)41(53)49(38)11/h16-19,23,26-27,29-30,32,34-38,51H,13-15,20-22,24-25H2,1-12H3,(H,47,52)/b28-23+/t26-,27-,29-,30-,32-,34-,35-,36-,37-,38+/m0/s1 |
| SMILES | CC[C@H](C)[C@@H]1C(=O)N2CCC[C@H]2C(=O)O[C@@H](C[C@H](C[C@@H]([C@@H](C3=N[C@H](CS3)/C=C(/C(=O)N[C@H](C(=O)N([C@H](C(=O)N1C)C)C)CC4=CC=C(C=C4)OC)\C)C)O)C)C(C)(C)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Luesch; Yoshida; Moore; Paul; Corbett Total structure determination of apratoxin A, a potent novel cytotoxin from the marine cyanobacterium Lyngbya majuscula Journal of the American Chemical Society 2001 123 (23) 5418-5423. | ||
|---|---|---|---|
| DOI | 10.1021/ja010453j | PMID | 11389621 |
SYNTHESES
| CITATION 1 | Ma D; Zou B; Cai G; Hu X; Liu JO Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities. Chemistry - A European Journal 2006 12 (29) 7615-7626. DOI: 10.1002/chem.200600599 PMID: 16832801 | ||
|---|---|---|---|
| CITATION 2 | Chen J; Forsyth CJ Total synthesis of the marine cyanobacterial cyclodepsipeptide apratoxin A. Proceedings of the National Academy of Sciences of the United States of America 2004 101 (33) 12067-12072. DOI: 10.1073/pnas.0402752101 PMID: 15231999 | ||
| CITATION 3 | Doi T; Numajiri Y; Munakata A; Takahashi T Total synthesis of apratoxin A. Organic Letters 2006 8 (3) 531-534. DOI: 10.1021/ol052907d PMID: 16435877 | ||
| CITATION 4 | Doi T Synthesis of the biologically active natural product cyclodepsipeptides apratoxin A and its analogues. Chemical and Pharmaceutical Bulletin 2014 62 (8) 735-743. DOI: 10.1248/cpb.c14-00268 PMID: 25087625 | ||
| CITATION 5 | Chen J; Forsyth CJ Total synthesis of apratoxin A. Journal of the American Chemical Society 2003 125 (29) 8734-8735. DOI: 10.1021/ja036050w PMID: 12862462 | ||
| CITATION 6 | Numajiri Y; Takahashi T; Doi T Total synthesis of (-)-apratoxin A, 34-epimer, and its oxazoline analogue. Chemistry – An Asian Journal 2009 4 (1) 111-125. DOI: 10.1002/asia.200800365 PMID: 19034894 | ||
| CITATION 7 | Doi T; Numajiri Y; Takahashi T; Takagi M; Shin-ya K Solid-phase total synthesis of (-)-apratoxin A and its analogues and their biological evaluation. Chemistry – An Asian Journal 2011 6 (1) 180-188. DOI: 10.1002/asia.201000549 PMID: 21080404 | ||
