Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA012989
PROPERTIES
| NPAID | NPA012989 |
|---|---|
| CLUSTER ID | 4814 |
| NODE ID | 3482 |
| NAME | CP-263,114 |
| FORMULA | C32H38O9 |
| MOLECULAR WEIGHT (Da) | 566.6470 |
| ACCURATE MASS (Da) | 566.2516 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Phoma |
| ORIGIN SPECIES | sp. |
| InChIKey | ZKTHSTMYOMUICQ-ONZBGVKBSA-N |
| InChI | InChI=1S/C32H38O9/c1-4-6-8-9-10-12-13-19-15-22-31(18-24(34)35)17-21-25(28(37)39-27(21)36)26-20(19)16-30(3,23(33)14-11-7-5-2)41-32(22,26)40-29(31)38/h4-7,15,19-20,26H,8-14,16-18H2,1-3H3,(H,34,35)/b6-4+,7-5+/t19-,20+,26-,30-,31-,32?/m0/s1 |
| SMILES | C/C=C/CCCCC[C@H]1C=C2C34OC(=O)[C@]2(CC(=O)O)CC2=C(C(=O)OC2=O)[C@@H]3[C@@H]1C[C@@](C)(C(=O)CC/C=C/C)O4 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Dabrah, Thomas T.; Harwood Jr., H. James; Huang, Liang H.; Jankovich, Nancy D.; Kaneko, Takushi; Li, Jian-Cheng; Lindsey, Saralyn; Moshier, Peter M.; Subashi, Timothy A.; Therrien, Michelle; Watts, Paul C. CP-225,917 and CP-263,114, novel ras farnesylation inhibitors from an unidentified fungus. I. Taxonomy, fermentation, isolation, and biochemical properties Journal of Antibiotics 1997 50 (1) 1-7. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.50.1 | PMID | 9066758 |
SYNTHESES
| CITATION 1 | Nicolaou KC; Jung JK; Yoon WH; He Y; Zhong YL; Baran PS The Absolute Configuration and Asymmetric Total Synthesis of the CP Molecules (CP-263,114 and CP-225,917, Phomoidrides B and A) We thank Drs. D. H. Huang, G. Siuzdak, and R. Chadha for assistance with NMR spectroscopy, mass spectrometry, and X-ray crystallography, respectively. This work was financially supported by the National Institutes of Health (USA), The Skaggs Institute for Chemical Biology, doctoral fellowships from the National Science Foundation (P.S.B.) and Boehringer Ingelheim (Y.H.), and grants from Array Biopharma, Boehringer Ingelheim, Schering Plough, Pfizer, Glaxo, Merck, Hoffmann-La Roche, DuPont, and Abbott Laboratories. Angewandte Chemie International Edition 2000 39 (10) 1829-1832. DOI: 10.1002/(sici)1521-3773(20000515)39:10<1829::aid-anie1829>3.0.co;2-6 PMID: 10934377 | ||
|---|---|---|---|
| CITATION 2 | Nicolaou KC; Zhong YL; Baran PS; Jung J; Choi HS; Yoon WH Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues. Journal of the American Chemical Society 2002 124 (10) 2202-2211. DOI: 10.1021/ja0120126 PMID: 11878974 | ||
| CITATION 3 | Nicolaou KC; Baran PS; Zhong YL; Fong KC; He Y; Yoon WH; Choi HS Total Synthesis of the CP Molecules CP-225,917 and CP-263,114- Part 2: Evolution of the Final Strategy. Angewandte Chemie International Edition 1999 38 (11) 1676-1678. DOI: 10.1002/(SICI)1521-3773(19990601)38:11<1676::AID-ANIE1676>3.0.CO;2-T PMID: 29710974 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C/C=C/CCCCC[C@@H]1C=C2[C@@]3(CC4=C([C@@H]5[C@H]1C[C@@H](O[C@@]52OC3=O)C(=O)CC/C=C/C)C(=O)OC4=O)CC(=O)O | Dabrah, Thomas T.; Harwood Jr., H. James; Huang, Liang H.; Jankovich, Nancy D.; Kaneko, Takushi; Li, Jian-Cheng; Lindsey, Saralyn; Moshier, Peter M.; Subashi, Timothy A.; Therrien, Michelle; Watts, Paul C. CP-225,917 and CP-263,114, novel ras farnesylation inhibitors from an unidentified fungus. I. Taxonomy, fermentation, isolation, and biochemical properties Journal of Antibiotics 1997 50 (1) 1-7. DOI: 10.7164/antibiotics.50.1 PMID: 9066758 | ||
| 2 | C/C=C/CCCCC[C@H]1C=C2C34OC(=O)[C@]2(CC(=O)O)CC2=C(C(=O)OC2=O)[C@@H]3[C@@H]1C[C@@](C)(C(=O)CC/C=C/C)O4 | Nicolaou KC; Zhong YL; Baran PS; Jung J; Choi HS; Yoon WH Total synthesis of the CP-molecules (CP-263,114 and CP-225,917, phomoidrides B and A). 3. Completion and synthesis of advanced analogues. Journal of the American Chemical Society 2002 124 (10) 2202-2211. DOI: 10.1021/ja0120126 PMID: 11878974 | ||
