Compounds
| ID | Spectrum Quality | Annotated Name |
|---|
COMPOUND NPA001250
PROPERTIES
| NPAID | NPA001250 |
|---|---|
| CLUSTER ID | 834 |
| NODE ID | 723 |
| NAME | Yatakemycin |
| FORMULA | C35H29N5O8S |
| MOLECULAR WEIGHT (Da) | 679.7110 |
| ACCURATE MASS (Da) | 679.1737 |
| ORIGIN ORGANISM TYPE | Bacterium |
| ORIGIN GENUS | Streptomyces |
| ORIGIN SPECIES | sp. TP-A0356 |
| InChIKey | CMFSXTISUXTEGX-QXPWRNTLSA-N |
| InChI | InChI=1S/C35H29N5O8S/c1-47-25-10-19-14(7-23(25)41)6-20(36-19)33(45)40-13-15-12-35(15)18-9-21(37-28(18)24(42)11-26(35)40)32(44)39-5-4-16-17-8-22(34(46)49-3)38-27(17)31(48-2)30(43)29(16)39/h6-11,15,36-38,41,43H,4-5,12-13H2,1-3H3/t15-,35-/m1/s1 |
| SMILES | COC1=C(O)C=C2C=C(C(=O)N3C[C@H]4C[C@@]45C3=CC(=O)C3=C5C=C(C(=O)N4CCC5=C6C=C(C(=O)SC)NC6=C(OC)C(O)=C54)N3)NC2=C1 |
ORIGINAL ISOLATION REFERENCE
| CITATION | Igarashi, Yasuhiro; Futamata, Katsuyuki; Fujita, Tsuyoshi; Sekine, Akira; Senda, Hisato; Naoki, Hideo; Furumai, Tamotsu Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356 Journal of Antibiotics 2003 56 (2) 107-113. | ||
|---|---|---|---|
| DOI | 10.7164/antibiotics.56.107 | PMID | 12715869 |
SYNTHESES
| CITATION 1 | Tichenor MS; Kastrinsky DB; Boger DL Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Journal of the American Chemical Society 2004 126 (27) 8396-8398. DOI: 10.1021/ja0472735 PMID: 15237994 | ||
|---|---|---|---|
| CITATION 2 | Okano K; Tokuyama H; Fukuyama T Total synthesis of (+)-yatakemycin. Journal of the American Chemical Society 2006 128 (22) 7136-7137. DOI: 10.1021/ja0619455 PMID: 16734447 | ||
| CITATION 3 | Tichenor MS; Trzupek JD; Kastrinsky DB; Shiga F; Hwang I; Boger DL Asymmetric total synthesis of (+)- and ent-(-)-yatakemycin and duocarmycin SA: evaluation of yatakemycin key partial structures and its unnatural enantiomer. Journal of the American Chemical Society 2006 128 (49) 15683-15696. DOI: 10.1021/ja064228j PMID: 17147378 | ||
| CITATION 4 | Tichenor MS; Boger DL Yatakemycin: total synthesis, DNA alkylation, and biological properties. Natural Product Reports 2008 25 (2) 220-226. DOI: 10.1039/b705665f PMID: 18389136 | ||
| CITATION 5 | Okano K; Tokuyama H; Fukuyama T Total synthesis of (+)-yatakemycin. Chemistry – An Asian Journal 2008 3 (2) 296-309. DOI: 10.1002/asia.200700282 PMID: 18000998 | ||
REVISIONS
| VERSION | SMILES | CITATION | ||
|---|---|---|---|---|
| Original Isolation | CC(=O)SC1=CC2=C3CCN(C3=C(C(=C2N1)OC)O)C(=O)C4=CC5=C(N4)C(=O)C=C6C57CC7CN6C(=O)C8=CC9=CC(=C(C=C9N8)O)OC | Igarashi, Yasuhiro; Futamata, Katsuyuki; Fujita, Tsuyoshi; Sekine, Akira; Senda, Hisato; Naoki, Hideo; Furumai, Tamotsu Yatakemycin, a novel antifungal antibiotic produced by Streptomyces sp. TP-A0356 Journal of Antibiotics 2003 56 (2) 107-113. DOI: 10.7164/antibiotics.56.107 PMID: 12715869 | ||
| 2 | COC1=C(O)C=C2C=C(C(=O)N3C[C@H]4C[C@@]45C3=CC(=O)C3=C5C=C(C(=O)N4CCC5=C6C=C(C(=O)SC)NC6=C(OC)C(O)=C54)N3)NC2=C1 | Tichenor MS; Kastrinsky DB; Boger DL Total synthesis, structure revision, and absolute configuration of (+)-yatakemycin. Journal of the American Chemical Society 2004 126 (27) 8396-8398. DOI: 10.1021/ja0472735 PMID: 15237994 | ||
