Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
WARNING - This compound is excluded from the NP Atlas. The information displayed is for reference only.
Reason: Structure flagged during revision as not known
Citation: Lazzara, Nicholas C; Rosano, Robert J; Vagadia, Purav P; Giovine, Matthew T; Bezpalko, Mark W; Piro, Nicholas A; Kassel, Wm Scott; Boyko, Walter J; Zubris, Deanna L; Schrader, Kevin K; Wedge, David E; Duke, Stephen O; Giuliano, Robert M Synthesis and Biological Evaluation of 6-[(1 R)-1-Hydroxyethyl]-2,4a( R),6( S),8a( R)-tetrahydropyrano-[3,2- b]-pyran-2-one and Structural Analogues of the Putative Structure of Diplopyrone. Journal of Organic Chemistry 2019 84 (2) 666-678. DOI: 10.1021/acs.joc.8b02490
COMPOUND NPA003874
PROPERTIES
| NPAID | NPA003874 |
|---|---|
| CLUSTER ID | None |
| NODE ID | None |
| NAME | Diplopyrone |
| FORMULA | C10H12O4 |
| MOLECULAR WEIGHT (Da) | 196.2020 |
| ACCURATE MASS (Da) | 196.0736 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Diplodia |
| ORIGIN SPECIES | mutila |
| InChIKey | YMKWNRDVGOVSHY-XGEHTFHBSA-N |
| InChI | InChI=1S/C10H12O4/c1-6(11)7-2-3-9-8(13-7)4-5-10(12)14-9/h2-9,11H,1H3/t6-,7+,8+,9+/m1/s1 |
| SMILES | C[C@@H](O)[C@@H]1C=C[C@@H]2OC(=O)C=C[C@@H]2O1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Evidente, Antonio; Maddau, Lucia; Spanu, Emanuela; Franceschini, Antonio; Lazzaroni, Silvia; Motta, Andrea Diplopyrone, a new phytotoxic tetrahydropyranpyran-2-one produced by Diplodia mutila, a fungus pathogen of cork oak Journal of Natural Products 2003 66 (2) 313-315. | ||
|---|---|---|---|
| DOI | 10.1021/np020367c | PMID | 12608876 |
SYNTHESES
| CITATION 1 | Maity S; Kanikarapu S; Marumudi K; Kunwar AC; Yadav JS; Mohapatra DK Asymmetric Total Synthesis of the Putative Structure of Diplopyrone. Journal of Organic Chemistry 2017 82 (9) 4561-4568. DOI: 10.1021/acs.joc.7b00086 PMID: 28388091 | ||
|---|---|---|---|
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H](C1C=CC2C(O1)C=CC(=O)O2)O | Evidente, Antonio; Maddau, Lucia; Spanu, Emanuela; Franceschini, Antonio; Lazzaroni, Silvia; Motta, Andrea Diplopyrone, a new phytotoxic tetrahydropyranpyran-2-one produced by Diplodia mutila, a fungus pathogen of cork oak Journal of Natural Products 2003 66 (2) 313-315. DOI: 10.1021/np020367c PMID: 12608876 | ||
| 2 | C[C@@H](O)[C@@H]1C=C[C@@H]2OC(=O)C=C[C@@H]2O1 | Sarotti, Ariel M In Silico Reassignment of (+)-Diplopyrone by NMR Calculations: Use of a DP4/J-DP4/DP4+/DIP Tandem to Revise Both Relative and Absolute Configuration. Journal of Organic Chemistry 2020 85 (17) 11566-11570. DOI: 10.1021/acs.joc.0c01563 PMID: 32786623 | ||
