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Compounds

COMPOUND NPA004208

STRUCTURE
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PROPERTIES
NPAID NPA004208
CLUSTER ID 95
NODE ID 90
NAME Candelalide A
FORMULA C25H34O4
MOLECULAR WEIGHT (Da) 398.5430
ACCURATE MASS (Da) 398.2457
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Sesquicillium
ORIGIN SPECIES candelabrum
InChIKey SCHPGLGCBCJZKD-YYHYCTJNSA-N
InChI InChI=1S/C25H34O4/c1-15-8-9-20-24(4,12-10-21-25(20,5)11-7-13-28-21)19(15)14-18-22(26)16(2)17(3)29-23(18)27-6/h7,13,19-21H,1,8-12,14H2,2-6H3/t19-,20-,21-,24-,25+/m1/s1
SMILES CC1=C(OC(=C(C1=O)C[C@@H]2C(=C)CC[C@@H]3[C@@]2(CC[C@@H]4[C@]3(CC=CO4)C)C)OC)C
ORIGINAL ISOLATION REFERENCE
CITATION Singh, S B; Zink, D L; Dombrowski, A W; Dezeny, G; Bills, G F; Felix, J P; Slaughter, R S; Goetz, M A Candelalides A-C: novel diterpenoid pyrones from fermentations of Sesquicillium candelabrum as blockers of the voltage-gated potassium channel Kv1.3 Organic Letters 2001 3 (2) 247-250.
DOI 10.1002/chin.200119162 PMID 11430046
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Sordariomycetes MycoBank 147550
Order Hypocreales MycoBank 5125
Family Bionectriaceae MycoBank 103887
Genus Sesquicillium MycoBank 122396
SYNTHESES
CITATION 1 Watanabe K; Iwasaki K; Abe T; Inoue M; Ohkubo K; Suzuki T; Katoh T Enantioselective total synthesis of (-)-candelalide A, a novel blocker of the voltage-gated potassium channel Kv1.3 for an immunosuppressive agent. Organic Letters 2005 7 (17) 3745-8. DOI: 10.1021/ol051398c PMID: 16092865
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