Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA002228
PROPERTIES
| NPAID | NPA002228 |
|---|---|
| CLUSTER ID | 1343 |
| NODE ID | 1132 |
| NAME | Actinoranone |
| FORMULA | C32H46O4 |
| MOLECULAR WEIGHT (Da) | 494.7160 |
| ACCURATE MASS (Da) | 494.3396 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. |
| InChIKey | VOPBJYDCUMJXOI-XFRWNCSNSA-N |
| InChI | InChI=1S/C32H46O4/c1-20(9-12-25-21(2)10-14-29-31(3,4)15-8-16-32(25,29)5)17-27(34)23-11-13-26(33)30-24(23)18-22(35-6)19-28(30)36-7/h10,17-19,23,25,27,29,34H,8-9,11-16H2,1-7H3/b20-17+/t23-,25-,27+,29-,32+/m0/s1 |
| SMILES | COC1=CC2=C(C(=O)CC[C@@H]2[C@H](O)/C=C(\C)CC[C@H]2C(C)=CC[C@H]3C(C)(C)CCC[C@]23C)C(OC)=C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Nam, Sang-Jip; Kauffman, Christopher A.; Paul, Lauren A.; Jensen, Paul R.; Fenical, William Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted streptomyces sp Organic Letters 2013 15 (21) 5400-5403. | ||
|---|---|---|---|
| DOI | 10.1021/ol402080s | PMID | 24152065 |
SYNTHESES
| CITATION 1 | Guo YA; Zhao M; Xu Z; Ye T Total Synthesis and Stereochemical Assignment of Actinoranone. Chemistry - A European Journal 2017 23 (15) 3572-3576. DOI: 10.1002/chem.201700476 PMID: 28152222 | ||
|---|---|---|---|
| CITATION 2 | Novaes LFT; Pastre JC Formal Total Synthesis of Actinoranone and Asymmetric Synthesis of Labda-7,13-(E)-dien-15-ol. Organic Letters 2017 19 (12) 3163-3166. DOI: 10.1021/acs.orglett.7b01287 PMID: 28562055 | ||
| CITATION 3 | Novaes LFT; Gonçalves KA; Trivella DBB; Pastre JC Formal Total Synthesis of Actinoranone: Synthesis Approaches and Cytotoxic Studies. Journal of Organic Chemistry 2018 83 (9) 5160-5176. DOI: 10.1021/acs.joc.8b00514 PMID: 29644851 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC1=CC[C@H]2[C@]([C@@H]1CC/C(=C/[C@H]([C@@H]3CCC(=O)C4=C(C=C(C=C34)OC)OC)O)/C)(CCCC2(C)C)C | Nam, Sang-Jip; Kauffman, Christopher A.; Paul, Lauren A.; Jensen, Paul R.; Fenical, William Actinoranone, a cytotoxic meroterpenoid of unprecedented structure from a marine adapted streptomyces sp Organic Letters 2013 15 (21) 5400-5403. DOI: 10.1021/ol402080s PMID: 24152065 | ||
| 2 | COC1=CC2=C(C(=O)CC[C@@H]2[C@H](O)/C=C(\C)CC[C@H]2C(C)=CC[C@H]3C(C)(C)CCC[C@]23C)C(OC)=C1 | Guo YA; Zhao M; Xu Z; Ye T Total Synthesis and Stereochemical Assignment of Actinoranone. Chemistry - A European Journal 2017 23 (15) 3572-3576. DOI: 10.1002/chem.201700476 PMID: 28152222 | ||
