Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA001236
PROPERTIES
| NPAID | NPA001236 |
|---|---|
| CLUSTER ID | 827 |
| NODE ID | 719 |
| NAME | Trachyspic acid |
| FORMULA | C20H28O9 |
| MOLECULAR WEIGHT (Da) | 412.4350 |
| ACCURATE MASS (Da) | 412.1733 |
| ORIGIN ORGANISM TYPE | Fungus |
| ORIGIN GENUS | Talaromyces |
| ORIGIN SPECIES | trachyspermus SANK 12191 |
| InChIKey | LQLCHKHILFZNKF-UAOJZALGSA-N |
| InChI | InChI=1S/C20H28O9/c1-2-3-4-5-6-7-8-9-13-12-28-20(16(13)23)10-14(17(24)25)19(29-20,18(26)27)11-15(21)22/h12,14H,2-11H2,1H3,(H,21,22)(H,24,25)(H,26,27)/t14-,19+,20+/m1/s1 |
| SMILES | CCCCCCCCCC1=CO[C@]2(C[C@H](C(=O)O)[C@@](CC(=O)O)(C(=O)O)O2)C1=O |
ORIGINAL ISOLATION REFERENCE
| CITATION | Shiozawa; Takahashi; Takatsu; Kinoshita; Tanzawa; Hosoya; Furuya; Furihata; Seto Trachyspic acid, a new metabolite produced by Talaromyces trachyspermus, that inhibits tumor cell heparanase: Taxonomy of the producing strain, fermentation, isolation, structural elucidation, and biological activity Journal of Antibiotics 1995 48 (5) 357-362. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.48.357 | PMID | 7797435 |
SYNTHESES
| CITATION 1 | Hirai K; Ooi H; Esumi T; Iwabuchi Y; Hatakeyama S Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration. Organic Letters 2003 5 (6) 857-859. DOI: 10.1021/ol0275264 PMID: 12633090 | ||
|---|---|---|---|
| CITATION 2 | Zammit SC; Ferro V; Hammond E; Rizzacasa MA Enantiospecific synthesis of the heparanase inhibitor (+)-trachyspic acid and stereoisomers from a common precursor. Organic & Biomolecular Chemistry 2007 5 (17) 2826-2834. DOI: 10.1039/b708594j PMID: 17700851 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CCCCCCCCCC1=COC2(C1=O)CC(C(O2)(CC(=O)O)C(=O)O)C(=O)O | Shiozawa; Takahashi; Takatsu; Kinoshita; Tanzawa; Hosoya; Furuya; Furihata; Seto Trachyspic acid, a new metabolite produced by Talaromyces trachyspermus, that inhibits tumor cell heparanase: Taxonomy of the producing strain, fermentation, isolation, structural elucidation, and biological activity Journal of Antibiotics 1995 48 (5) 357-362. DOI: 10.7164/antibiotics.48.357 PMID: 7797435 | ||
| 2 | CCCCCCCCCC1=CO[C@]2(C[C@H](C(=O)O)[C@@](CC(=O)O)(C(=O)O)O2)C1=O | Hirai K; Ooi H; Esumi T; Iwabuchi Y; Hatakeyama S Total synthesis of (+/-)-trachyspic acid and determination of the relative configuration. Organic Letters 2003 5 (6) 857-859. DOI: 10.1021/ol0275264 PMID: 12633090 | ||
