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Compounds

COMPOUND NPA021187

STRUCTURE
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PROJECT MOLECULE TO GLOBAL VIEW See Global
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PROPERTIES
NPAID NPA021187
CLUSTER ID 6624
NODE ID 4593
NAME Vermiculine
FORMULA C20H24O8
MOLECULAR WEIGHT (Da) 392.4040
ACCURATE MASS (Da) 392.1471
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Penicillium
ORIGIN SPECIES vermiculatum
InChIKey CFDVIOQSLRJWSU-IIWBTEQSSA-N
InChI InChI=1S/C20H24O8/c1-13(21)11-17-7-3-15(23)6-10-20(26)28-18(12-14(2)22)8-4-16(24)5-9-19(25)27-17/h5-6,9-10,17-18H,3-4,7-8,11-12H2,1-2H3/b9-5+,10-6?
SMILES CC(=O)CC1CCC(=O)/C=C/C(=O)OC(CCC(=O)C=CC(=O)O1)CC(=O)C
ORIGINAL ISOLATION REFERENCE
CITATION Fuska J; Nemec P; Kuhr I VERMICULINE, A NEW ANTIPROTOZOAL ANTIBIOTIC FROM PENICILLIUM VERMICULATUM Journal of Antibiotics 1972 25 (4) 208-211.
DOI 10.7164/antibiotics.25.208 PMID 4559271
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Eurotiomycetes MycoBank 147545
Order Eurotiales MycoBank 5042
Family Aspergillaceae MycoBank 1131492
Genus Penicillium MycoBank 5073
SYNTHESES
CITATION 1 Corey EJ; Nicolaou KC; Toru T Letter: Total synthesis of (plus or minus)-vermiculine. Journal of the American Chemical Society 1975 97 (8) 2287-8. DOI: 10.1021/ja00841a058 PMID: 1133413
CITATION 2 Steib P; Breit B Concise Total Synthesis of (-)-Vermiculine through a Rhodium-Catalyzed C Chemistry - A European Journal 2019 25 (14) 3532-3535. DOI: 10.1002/chem.201900216 PMID: 30672028
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