Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA000478
PROPERTIES
| NPAID | NPA000478 |
|---|---|
| CLUSTER ID | 371 |
| NODE ID | 335 |
| NAME | Panepophenanthrin |
| FORMULA | C22H28O8 |
| MOLECULAR WEIGHT (Da) | 420.4580 |
| ACCURATE MASS (Da) | 420.1784 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Panus |
| ORIGIN SPECIES | rudis Fr. IFO 8994 |
| InChIKey | WQBRQZUREPTGLI-ODDMXWQNSA-N |
| InChI | InChI=1S/C22H28O8/c1-19(2,26)5-6-21-9-7-8-10(13(24)16-15(28-16)12(8)23)11(21)14(25)17-18(29-17)22(21,27)30-20(9,3)4/h5-7,9-11,13-18,24-27H,1-4H3/b6-5+/t9-,10-,11-,13-,14-,15-,16+,17+,18+,21-,22+/m1/s1 |
| SMILES | CC1([C@H]2C=C3[C@H]([C@H]4[C@@]2([C@@](O1)([C@@H]5[C@H]([C@@H]4O)O5)O)/C=C/C(C)(C)O)[C@H]([C@H]6[C@@H](C3=O)O6)O)C |
ORIGINAL ISOLATION REFERENCE
| CITATION | Sekizawa, Ryuichi; Ikeno, Souichi; Nakamura, Hikaru; Naganawa, Hiroshi; Matsui, Susumu; Iinuma, Hironobu; Takeuchi, Tomio Panepophenanthrin, from a mushroom strain, a novel inhibitor of the ubiquitin-activating enzyme Journal of Natural Products 2002 65 (10) 1491-1493. | ||
|---|---|---|---|
| DOI | 10.1021/np020098q | PMID | 12398550 |
SYNTHESES
| CITATION 1 | Lei X; Johnson RP; Porco JA Total synthesis of the ubiquitin-activating enzyme inhibitor (+)-panepophenanthrin. Angewandte Chemie International Edition 2003 42 (33) 3913-3917. DOI: 10.1002/anie.200351862 PMID: 12949867 | ||
|---|---|---|---|
| CITATION 2 | Moses JE; Commeiras L; Baldwin JE; Adlington RM Total synthesis of panepophenanthrin. Organic Letters 2003 5 (17) 2987-2988. DOI: 10.1021/ol0349817 PMID: 12916962 | ||
| CITATION 3 | Matsuzawa M; Kakeya H; Yamaguchi J; Shoji M; Onose R; Osada H; Hayashi Y Enantio- and diastereoselective total synthesis of (+)-panepophenanthrin, a ubiquitin-activating enzyme inhibitor, and biological properties of its new derivatives. Chemistry – An Asian Journal 2006 1 (6) 845-851. DOI: 10.1002/asia.200600199 PMID: 17441127 | ||
