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Compounds

COMPOUND NPA003674

STRUCTURE
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PROPERTIES
NPAID NPA003674
CLUSTER ID 193
NODE ID 181
NAME Brevianamide A
FORMULA C21H23N3O3
MOLECULAR WEIGHT (Da) 365.4330
ACCURATE MASS (Da) 365.1739
ORIGIN ORGANISM TYPE Fungus
ORIGIN GENUS Chaetomium
ORIGIN SPECIES sp.
InChIKey MWOFPQAPILIIPR-DJJZHVJBSA-N
InChI InChI=1S/C21H23N3O3/c1-18(2)14-10-19-8-5-9-24(19)17(27)20(14,23-16(19)26)11-21(18)15(25)12-6-3-4-7-13(12)22-21/h3-4,6-7,14,22H,5,8-11H2,1-2H3,(H,23,26)/t14-,19+,20+,21-/m0/s1
SMILES CC1(C)[C@@H]2C[C@@]34CCCN3C(=O)[C@]2(C[C@@]12NC1=CC=CC=C1C2=O)NC4=O
ORIGINAL ISOLATION REFERENCE
CITATION Birch, AJ; Wright, JJ The brevianamides: a new class of fungal alkaloid Journal of the Chemical Society D: Chemical Communications 1969 (12) 644b-645.
DOI 10.1039/c2969000644b PMID -
ORIGINAL ISOLATION TAXONOMY
RANK NAME DB LINK NCBI
Domain Eukarya - 2759
Kingdom Fungi MycoBank 4751
Phylum Ascomycota MycoBank 4890
Class Sordariomycetes MycoBank 147550
Order Sordariales MycoBank 5139
Family Chaetomiaceae MycoBank 35718
Genus Chaetomium MycoBank 5149
REVISIONS
VERSION SMILES CITATION
Original Isolation CC1(C2CC34CCCN3C(=O)C2(CC15C(=O)C6=CC=CC=C6N5)NC4=O)C Birch, AJ; Wright, JJ The brevianamides: a new class of fungal alkaloid Journal of the Chemical Society D: Chemical Communications 1969 (12) 644b-645. DOI: 10.1039/c2969000644b
2 CC1(C)[C@@H]2C[C@@]34CCCN3C(=O)[C@]2(C[C@@]12NC1=CC=CC=C1C2=O)NC4=O Mansour, Ali; Gagosz, Fabien Expedited Total Synthesis of (±)-Brevianamide A via the Strategic Use of Gold(I) Catalysis. Organic Letters 2022 24 (39) 7200-7204. DOI: 10.1021/acs.orglett.2c02971 PMID: 36170661
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