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Compounds

COMPOUND NPA019894

STRUCTURE
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PROPERTIES
NPAID NPA019894
CLUSTER ID 3933
NODE ID 2937
NAME Arenicolide A
FORMULA C45H72O12
MOLECULAR WEIGHT (Da) 805.0590
ACCURATE MASS (Da) 804.5024
ORIGIN ORGANISM TYPE Bacterium
ORIGIN GENUS Salinispora
ORIGIN SPECIES arenicola
InChIKey BKUKTJSDOUXYFL-ZNDFHVDNSA-N
InChI InChI=1S/C45H72O12/c1-11-16-35(48)42(54-9)44-45(6,57-44)39(49)21-15-20-38-43(55-10)41(51)32(5)28-31(4)24-26-34(47)37(53-8)19-14-17-29(2)27-30(3)23-25-33(46)36(52-7)18-12-13-22-40(50)56-38/h12-13,15,18,20,22-29,32-39,41-44,46-49,51H,11,14,16-17,19,21H2,1-10H3/b18-12+,20-15+,22-13+,25-23+,26-24+,30-27+,31-28+/t29?,32-,33-,34-,35+,36-,37-,38+,39+,41+,42-,43+,44-,45-/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](OC)[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)OC)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](OC)[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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