Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA003989
PROPERTIES
| NPAID | NPA003989 |
|---|---|
| CLUSTER ID | 2128 |
| NODE ID | 1699 |
| NAME | Torreyanic acid |
| FORMULA | C38H44O12 |
| MOLECULAR WEIGHT (Da) | 692.7580 |
| ACCURATE MASS (Da) | 692.2833 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Pestalotiopsis |
| ORIGIN SPECIES | microspora |
| InChIKey | DQBVXDMPCDAQGS-MBKAVXJQSA-N |
| InChI | InChI=1S/C38H44O12/c1-5-7-9-11-21-23-24-25(28(40)32-36(49-32,29(24)41)15-13-18(3)33(42)43)30(48-21)38-20(17-47-22(26(23)38)12-10-8-6-2)27(39)31-37(50-31,35(38)46)16-14-19(4)34(44)45/h13-14,17,21-23,26,30-32H,5-12,15-16H2,1-4H3,(H,42,43)(H,44,45)/b18-13+,19-14+/t21-,22+,23-,26-,30?,31-,32-,36+,37-,38-/m0/s1 |
| SMILES | CCCCC[C@H]1[C@@H]2[C@@H]3[C@H](OC=C4[C@]3(C(O1)C5=C2C(=O)[C@@]6([C@H](C5=O)O6)C/C=C(\C)/C(=O)O)C(=O)[C@@]7([C@H](C4=O)O7)C/C=C(\C)/C(=O)O)CCCCC |
ORIGINAL ISOLATION REFERENCE
| CITATION | Lee, Julie C.; Strobel, Gary A.; Lobkovsky, Emil; Clardy, Jon Torreyanic Acid: A Selectively Cytotoxic Quinone Dimer from the Endophytic Fungus Pestalotiopsis microspora Journal of Organic Chemistry 1996 61 (10) 3232-3233. | ||
|---|---|---|---|
| DOI | 10.1021/jo960471x | PMID | - |
SYNTHESES
| CITATION 1 | Li C; Johnson RP; Porco JA Total synthesis of the quinone epoxide dimer (+)-torreyanic acid: application of a biomimetic oxidation/electrocyclization/Diels-Alder dimerization cascade. Journal of the American Chemical Society 2003 125 (17) 5095-106. DOI: 10.1021/ja021396c PMID: 12708860 | ||
|---|---|---|---|
| CITATION 2 | Mehta G; Pan SC Total synthesis of the novel, biologically active epoxyquinone dimer (+/-)-torreyanic acid: a biomimetic approach. Organic Letters 2004 6 (22) 3985-8. DOI: 10.1021/ol0483551 PMID: 15496080 | ||
