Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA007276
PROPERTIES
| NPAID | NPA007276 |
|---|---|
| CLUSTER ID | 3262 |
| NODE ID | 2481 |
| NAME | Spiruchostatin A |
| FORMULA | C20H31N3O6S2 |
| MOLECULAR WEIGHT (Da) | 473.6170 |
| ACCURATE MASS (Da) | 473.1654 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Pseudomonas |
| ORIGIN SPECIES | sp. |
| InChIKey | XFLBOEMFLGLWFF-VBTKZJTPSA-N |
| InChI | InChI=1S/C20H31N3O6S2/c1-11(2)18-15(24)9-17(26)29-13-6-4-5-7-30-31-10-14(20(28)23-18)22-19(27)12(3)21-16(25)8-13/h4,6,11-15,18,24H,5,7-10H2,1-3H3,(H,21,25)(H,22,27)(H,23,28)/b6-4+/t12-,13-,14+,15-,18+/m0/s1 |
| SMILES | CC(C)[C@H]1NC(=O)[C@H]2CSSCC/C=C/[C@@H](CC(=O)N[C@@H](C)C(=O)N2)OC(=O)C[C@@H]1O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Masuoka, Yuhta; Nagai, Atsuko; Shin-ya, Kazuo; Furihata, Kazuo; Nagai, Koji; Suzuki, Ken-Ichi; Hayakawa, Yoichi; Seto, Haruo Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp Tetrahedron Letters 2001 42 (1) 41-44. | ||
|---|---|---|---|
| DOI | 10.1016/s0040-4039(00)01874-8 | PMID | - |
SYNTHESES
| CITATION 1 | Calandra NA; Cheng YL; Kocak KA; Miller JS Total synthesis of Spiruchostatin A via chemoselective macrocyclization using an accessible enantiomerically pure latent thioester. Organic Letters 2009 11 (9) 1971-1974. DOI: 10.1021/ol900436f PMID: 19331423 | ||
|---|---|---|---|
| CITATION 2 | Yurek-George A; Habens F; Brimmell M; Packham G; Ganesan A Total synthesis of spiruchostatin A, a potent histone deacetylase inhibitor. Journal of the American Chemical Society 2004 126 (4) 1030-1031. DOI: 10.1021/ja039258q PMID: 14746465 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | C[C@@H]1C(=O)N[C@@H]2CSSCC/C=C/C(CC(=O)N1)OC(=O)CC(C(NC2=O)C(C)C)O | Masuoka, Yuhta; Nagai, Atsuko; Shin-ya, Kazuo; Furihata, Kazuo; Nagai, Koji; Suzuki, Ken-Ichi; Hayakawa, Yoichi; Seto, Haruo Spiruchostatins A and B, novel gene expression-enhancing substances produced by Pseudomonas sp Tetrahedron Letters 2001 42 (1) 41-44. DOI: 10.1016/s0040-4039(00)01874-8 | ||
| 2 | CC(C)[C@H]1NC(=O)[C@H]2CSSCC/C=C/[C@@H](CC(=O)N[C@@H](C)C(=O)N2)OC(=O)C[C@@H]1O | Calandra NA; Cheng YL; Kocak KA; Miller JS Total synthesis of Spiruchostatin A via chemoselective macrocyclization using an accessible enantiomerically pure latent thioester. Organic Letters 2009 11 (9) 1971-1974. DOI: 10.1021/ol900436f PMID: 19331423 | ||
