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Compounds

COMPOUND NPA015008

STRUCTURE
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PROPERTIES
NPAID NPA015008
CLUSTER ID 3933
NODE ID 2937
NAME Arenicolide B
FORMULA C44H70O12
MOLECULAR WEIGHT (Da) 791.0320
ACCURATE MASS (Da) 790.4867
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Salinispora
ORIGIN SPECIES arenicola
InChIKey XRUWJLVJXCQEIB-MOAOXDCKSA-N
InChI InChI=1S/C44H70O12/c1-10-15-35(48)41(53-8)43-44(6,56-43)38(49)20-14-19-37-42(54-9)40(51)31(5)27-30(4)23-25-34(47)36(52-7)18-13-16-28(2)26-29(3)22-24-33(46)32(45)17-11-12-21-39(50)55-37/h11-12,14,17,19,21-28,31-38,40-43,45-49,51H,10,13,15-16,18,20H2,1-9H3/b17-11+,19-14+,21-12+,24-22+,25-23+,29-26+,30-27+/t28?,31-,32-,33-,34-,35+,36-,37+,38+,40+,41-,42+,43-,44-/m1/s1
SMILES CCC[C@H](O)[C@@H](OC)[C@H]1O[C@]1(C)[C@@H](O)C/C=C/[C@@H]1OC(=O)/C=C/C=C/[C@@H](O)[C@H](O)/C=C/C(C)=C/C(C)CCC[C@@H](OC)[C@H](O)/C=C/C(C)=C/[C@@H](C)[C@H](O)[C@H]1OC
ORIGINAL ISOLATION REFERENCE
CITATION Williams, Philip G.; Miller, Eric D.; Asolkar, Ratnakar N.; Jensen, Paul R.; Fenical, William Arenicolides A-C, 26-membered ring macrolides from the marine actinomycete Salinispora arenicola Journal of Organic Chemistry 2007 72 (14) 5025-5034.
DOI 10.1021/jo061878x PMID 17266372
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Bacteria LPSN 2
Phylum Actinobacteria LPSN 201174
Class Actinobacteria LPSN -
Order Micromonosporales LPSN 85008
Family Micromonosporaceae LPSN 28056
Genus Salinispora LPSN 168694
REVISIONS
VERSION SMILES CITATION
Original Isolation CCC[C@@H]([C@H](C1C(O1)(C)[C@H](C/C=C/[C@H]2[C@@H]([C@H]([C@@H](/C=C(/C=C/[C@H]([C@@H](CCCC(/C=C(/C=C/[C@H]([C@@H](/C=C/C=C/C(=O)O2)O)O)\C)C)OC)O)\C)C)O)OC)O)OC)O Williams, Philip G.; Miller, Eric D.; Asolkar, Ratnakar N.; Jensen, Paul R.; Fenical, William Arenicolides A-C, 26-membered ring macrolides from the marine actinomycete Salinispora arenicola Journal of Organic Chemistry 2007 72 (14) 5025-5034. DOI: 10.1021/jo061878x PMID: 17266372
2 CCC[C@H](O)[C@@H](OC)[C@H]1O[C@]1(C)[C@@H](O)C/C=C/[C@@H]1OC(=O)/C=C/C=C/[C@@H](O)[C@H](O)/C=C/C(C)=C/C(C)CCC[C@@H](OC)[C@H](O)/C=C/C(C)=C/[C@@H](C)[C@H](O)[C@H]1OC Nagumo, Shinji; Nakano, Taeko; Hata, Kyomi; Mizukami, Megumi; Miyashita, Masaaki Stereoselective synthesis of the C(25)-C(36) segment of arenicolides A and B: determination of the configuration of the trisubstituted epoxide. Organic Letters 2010 12 (5) 908-11. DOI: 10.1021/ol902750e PMID: 20112944
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