Compounds
ID | Spectrum Quality | Annotated Name |
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COMPOUND NPA012290
PROPERTIES
NPAID | NPA012290 |
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CLUSTER ID | 348 |
NODE ID | 314 |
NAME | Indoxamycin B |
FORMULA | C22H30O4 |
MOLECULAR WEIGHT (Da) | 358.4780 |
ACCURATE MASS (Da) | 358.2144 |
ORIGIN ORGANISM TYPE | Bacterium |
ORIGIN GENUS | Streptomyces |
ORIGIN SPECIES | sp. |
InChIKey | JBEJQFQKKHSILD-NLZUSZHWSA-N |
InChI | InChI=1S/C22H30O4/c1-7-13(2)18-20(5)10-14(3)17-21(20,6)19(26-18)15(4)11-22(17,12-23)9-8-16(24)25/h7-11,17-19,23H,12H2,1-6H3,(H,24,25)/b9-8+,13-7-/t17-,18-,19-,20-,21+,22+/m0/s1 |
SMILES | C/C=C(/C)[C@@H]1O[C@H]2C(C)=C[C@](/C=C/C(=O)O)(CO)[C@H]3C(C)=C[C@]1(C)[C@@]23C |
ORIGINAL ISOLATION REFERENCE
CITATION | Sato, Seizo; Iwata, Fumie; Mukai, Takako; Yamada, Shoichi; Takeo, Jiro; Abe, Akihisa; Kawahara, Hiroyuki Indoxamycins A-F. Cytotoxic tricycklic polypropionates from a marine-derived actinomycete Journal of Organic Chemistry 2009 74 (15) 5502-5509. | ||
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DOI | 10.1021/jo900667j | PMID | 19572603 |
SYNTHESES
CITATION 1 | Jeker OF; Carreira EM Total synthesis and stereochemical reassignment of (±)-indoxamycin B. Angewandte Chemie International Edition 2012 51 (14) 3474-3477. DOI: 10.1002/anie.201109175 PMID: 22345071 |
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REVISIONS
VERSION | SMILES | CITATION | ||
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Original Isolation | C/C=C(/C)\[C@@H]1[C@@]2(C=C([C@H]3[C@@]2([C@@H](O1)C(=C[C@@]3(CO)/C=C/C(=O)O)C)C)C)C | Sato, Seizo; Iwata, Fumie; Mukai, Takako; Yamada, Shoichi; Takeo, Jiro; Abe, Akihisa; Kawahara, Hiroyuki Indoxamycins A-F. Cytotoxic tricycklic polypropionates from a marine-derived actinomycete Journal of Organic Chemistry 2009 74 (15) 5502-5509. DOI: 10.1021/jo900667j PMID: 19572603 | ||
2 | C/C=C(/C)[C@@H]1O[C@H]2C(C)=C[C@](/C=C/C(=O)O)(CO)[C@H]3C(C)=C[C@]1(C)[C@@]23C | Jeker OF; Carreira EM Total synthesis and stereochemical reassignment of (±)-indoxamycin B. Angewandte Chemie International Edition 2012 51 (14) 3474-3477. DOI: 10.1002/anie.201109175 PMID: 22345071 |