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Compounds

COMPOUND NPA012290

STRUCTURE
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PROPERTIES
NPAID NPA012290
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.
DOI 10.1021/jo900667j PMID 19572603
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Actinobacteria LPSN 201174
Class Actinobacteria LPSN -
Order Streptomycetales LPSN 85011
Family Streptomycetaceae LPSN 2062
Genus Streptomyces LPSN 1883
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
REVISIONS
VERSION SMILES CITATION
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
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