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Compounds

COMPOUND NPA020328

STRUCTURE
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PROPERTIES
NPAID NPA020328
CLUSTER ID 6440
NODE ID 4453
NAME Kedarcidin
FORMULA C53H60ClN3O16
MOLECULAR WEIGHT (Da) 1030.5210
ACCURATE MASS (Da) 1029.3662
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Streptoalloteichus
ORIGIN SPECIES sp. (ATCC 53650)
InChIKey GFTRTMUGNRZABD-DIKUUKFSSA-N
InChI InChI=1S/C53H60ClN3O16/c1-25(2)67-38-18-29-17-35(58)33(21-32(29)45(64-8)46(38)65-9)50(61)56-34-20-31-15-16-37(49(54)55-31)70-39-19-30-14-13-28(40(24-66-51(34)62)71-42-22-36(59)44(57(6)7)26(3)68-42)11-10-12-41-53(30,73-41)48(39)72-43-23-52(5,63)47(60)27(4)69-43/h11,15-19,21,25-27,34,36,39-44,47-48,58-60,63H,20,22-24H2,1-9H3,(H,56,61)/b28-11+/t26?,27?,34?,36?,39?,40?,41?,42?,43?,44?,47?,48-,52?,53+/m0/s1
SMILES COC1=C(OC)C2=CC(C(=O)NC3CC4=NC(Cl)=C(C=C4)OC4C=C5C#C/C(=C\C#CC6O[C@]56[C@H]4OC4CC(C)(O)C(O)C(C)O4)C(OC4CC(O)C(N(C)C)C(C)O4)COC3=O)=C(O)C=C2C=C1OC(C)C
ORIGINAL ISOLATION REFERENCE
CITATION Leet, JE; Schroeder, DR; Hofstead, SJ; Golik, J; Colson, KL; Huang, S; Klohr, SE; Doyle, TW; Matson, JA Kedarcidin, a new chromoprotein antitumor antibiotic: structure elucidation of kedarcidin chromophore Journal of the American Chemical Society 1992 114 (20) 7946-7948.
DOI 10.1021/ja00046a071 PMID -
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Actinobacteria LPSN 201174
Class Actinobacteria LPSN -
Order Pseudonocardiales LPSN 85010
Family Pseudonocardiaceae LPSN 2070
Genus Streptoalloteichus LPSN 2016
REVISIONS
VERSION SMILES CITATION
Original Isolation CC1C(C(CC(O1)OC\2COC(=O)C(CC3=NC(=C(C=C3)OC4C=C5C#C/C2=C\C#CC6C5(C4OC7CC(C(C(O7)C)O)(C)O)O6)Cl)NC(=O)C8=C(C=C9C=C(C(=C(C9=C8)OC)OC)OC(C)C)O)O)N(C)C Leet, JE; Schroeder, DR; Hofstead, SJ; Golik, J; Colson, KL; Huang, S; Klohr, SE; Doyle, TW; Matson, JA Kedarcidin, a new chromoprotein antitumor antibiotic: structure elucidation of kedarcidin chromophore Journal of the American Chemical Society 1992 114 (20) 7946-7948. DOI: 10.1021/ja00046a071
2 COC1=C(OC)C2=CC(C(=O)NC3CC4=NC(Cl)=C(C=C4)OC4C=C5C#C/C(=C\C#CC6O[C@]56[C@H]4OC4CC(C)(O)C(O)C(C)O4)C(OC4CC(O)C(N(C)C)C(C)O4)COC3=O)=C(O)C=C2C=C1OC(C)C Ren, Feng; Hogan, Philip C; Anderson, Alan J; Myers, Andrew G Kedarcidin chromophore: synthesis of its proposed structure and evidence for a stereochemical revision. Journal of the American Chemical Society 2007 129 (17) 5381-3. DOI: 10.1021/ja071205b PMID: 17417855
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