Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA006799
PROPERTIES
| NPAID | NPA006799 |
|---|---|
| CLUSTER ID | 3107 |
| NODE ID | 2372 |
| NAME | Azaspirene |
| FORMULA | C21H23NO5 |
| MOLECULAR WEIGHT (Da) | 369.4170 |
| ACCURATE MASS (Da) | 369.1576 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Neosartorya |
| ORIGIN SPECIES | sp. |
| InChIKey | QLKGRMRPKQNCRR-HSWRZQHOSA-N |
| InChI | InChI=1S/C21H23NO5/c1-3-4-5-9-12-16-14(2)17(23)21(27-16)18(24)20(26,22-19(21)25)13-15-10-7-6-8-11-15/h4-12,18,24,26H,3,13H2,1-2H3,(H,22,25)/b5-4+,12-9+/t18-,20+,21-/m1/s1 |
| SMILES | CC/C=C/C=C/C1=C(C)C(=O)[C@]2(O1)C(=O)N[C@](O)(CC1=CC=CC=C1)[C@H]2O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Asami, Yukihiro; Kakeya, Hideaki; Onose, Rie; Yoshida, Arika; Matsuzaki, Hiroshi; Osada, Hiroyuki Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp Organic Letters 2002 4 (17) 2845-2848. | ||
|---|---|---|---|
| DOI | 10.1021/ol020104+ | PMID | 12182570 |
SYNTHESES
| CITATION 1 | Hayashi Y; Shoji M; Yamaguchi J; Sato K; Yamaguchi S; Mukaiyama T; Sakai K; Asami Y; Kakeya H; Osada H Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. Journal of the American Chemical Society 2002 124 (41) 12078-9. DOI: 10.1021/ja0276826 PMID: 12371831 | ||
|---|---|---|---|
| CITATION 2 | Kang T; Jo D; Han S Six-Step Total Synthesis of Azaspirene. Journal of Organic Chemistry 2017 82 (18) 9335-9341. DOI: 10.1021/acs.joc.7b01224 PMID: 28699341 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC/C=C/C=C/C1=C(C(=O)[C@@]2(O1)[C@H]([C@@](NC2=O)(CC3=CC=CC=C3)O)O)C | Asami, Yukihiro; Kakeya, Hideaki; Onose, Rie; Yoshida, Arika; Matsuzaki, Hiroshi; Osada, Hiroyuki Azaspirene: a novel angiogenesis inhibitor containing a 1-oxa-7-azaspiro[4.4]non-2-ene-4,6-dione skeleton produced by the fungus Neosartorya sp Organic Letters 2002 4 (17) 2845-2848. DOI: 10.1021/ol020104+ PMID: 12182570 | ||
| 2 | CC/C=C/C=C/C1=C(C)C(=O)[C@]2(O1)C(=O)N[C@](O)(CC1=CC=CC=C1)[C@H]2O | Hayashi Y; Shoji M; Yamaguchi J; Sato K; Yamaguchi S; Mukaiyama T; Sakai K; Asami Y; Kakeya H; Osada H Asymmetric total synthesis of (-)-azaspirene, a novel angiogenesis inhibitor. Journal of the American Chemical Society 2002 124 (41) 12078-9. DOI: 10.1021/ja0276826 PMID: 12371831 | ||
