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Compounds

COMPOUND NPA004285

STRUCTURE
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PROPERTIES
NPAID NPA004285
CLUSTER ID 22
NODE ID 21
NAME Aigialospirol
FORMULA C19H22O8
MOLECULAR WEIGHT (Da) 378.3770
ACCURATE MASS (Da) 378.1315
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Aigialus
ORIGIN SPECIES parvus BCC 5311
InChIKey XOJJZYZCRNGOFV-YLZOTCFESA-N
InChI InChI=1S/C19H22O8/c1-9-4-3-5-19(26-9)17(22)13(21)8-14(27-19)16-11-6-10(24-2)7-12(20)15(11)18(23)25-16/h3,5-7,9,13-14,16-17,20-22H,4,8H2,1-2H3/t9-,13-,14+,16-,17-,19+/m0/s1
SMILES C[C@H]1CC=C[C@]2(O1)[C@H]([C@H](C[C@@H](O2)[C@@H]3C4=CC(=CC(=C4C(=O)O3)O)OC)O)O
ORIGINAL ISOLATION REFERENCE
CITATION Vongvilai, Pornrapee; Isaka, Masahiko; Kittakoop, Prasat; Srikitikulchai, Prasert; Kongsaeree, Palangpon; Thebtaranonth, Yodhathai Ketene Acetal and Spiroacetal Constituents of the Marine Fungus Aigialus parvus BCC 5311 Journal of Natural Products 2004 67 (3) 457-460.
DOI 10.1021/np030344d PMID 15043431
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Dothideomycetes MycoBank 147541
Order Pleosporales MycoBank 92860
Family Aigialaceae MycoBank 715274
Genus Aigialus MycoBank 193126
SYNTHESES
CITATION 1 Figueroa R; Hsung RP; Guevarra CC An enantioselective total synthesis of (+)-aigialospirol. Organic Letters 2007 9 (23) 4857-4859. DOI: 10.1021/ol702195w PMID: 17949099
CITATION 2 Figueroa R; Feltenberger JB; Guevarra CC; Hsung RP Two Remarkable Epimerizations Imperative for the Success of an Asymmetric Total Synthesis of (+)-Aigialospirol. Science China Chemistry 2011 54 (1) 31-42. DOI: 10.1007/s11426-010-4176-8 PMID: 21221423
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